Charming Vacation Rentals in Islamorada, FL

Cheeca Lodge & Spa
Resort
81801 Overseas Highway Mile Marker 82, Islamorada, FL, FL 33036, USA

Positioned on 27 acres of lush gardens and 1000 feet of private waterfront, Cheeca Lodge & Spa is a luxury resort in Islamorada, Florida. It features a 9-hole par 3 golf course, on-site spa, and 525-foot fishing pier. Each guestroom includes dark hardwood furniture and a balcony with views of the resort. Guests can watch movies on the 42-inch flat-screen TV with DVD player or browse the internet with free WiFi. An in-room safe and coffee maker are also provided. Adult and family-style swimming pools can be enjoyed at the resort. Additionally, a fully equipped fitness center, 6 tennis courts, and a full-service watersports facility are open to guests. Three restaurants and a tiki bar are located on-site at Cheeca Lodge & Spa. Atlantic’s Edge offers tropically-inspired cuisine amid a classic décor while Nikai Sushi Bar & Restaurant serves nigiri, sashimi, and more. Downtown Key Largo is a 20-minute drive from Cheeca Lodge & Spa. Long Key State Park is 13.7 miles from the resort.

Guest Reviews:

- "It was a wonderful experience." - "I was visiting for my birthday and it was one of the most beautiful places I’ve ever visited. The people were very welco" - "Took my 20-year-old niece with me I don’t think it’s a great place for younger kids" - "Did enjoy" - "Great romantic place to stay with gorgeous views from everywhere." - "Great facility warm and informative employees" - "Spectacular but make sure you’re not next door to any noisy dogs!"

Cheeca Lodge & Spa
Resort
81801 Overseas Highway, Mile Marker 82, Islamorada, FL, 33036, USA

Luxury resort on the beach, with 3 outdoor pools
Spend the day relaxing at Cheeca Lodge & Spa's private sand beach, practicing your swing on the golf course, or pampering yourself at the full-service spa. Then enjoy a meal at one of the resort's 3 restaurants.
Cheeca Lodge & Spa offers 243 accommodations with safes and coffee/tea makers. Rooms open to balconies. Beds feature premium bedding. 47-inch LED televisions come with premium cable channels.

Bathrooms include bathrobes, slippers, designer toiletries, and complimentary toiletries. Business-friendly amenities include desks and phones; free local calls are provided (restrictions may apply). Additionally, rooms include hair dryers and irons/ironing boards. In-room massages and hypo-allergenic bedding can be requested. A nightly turndown service is provided and housekeeping is offered daily.


Guests can play rounds at the 9-hole golf course and enjoy other recreation facilities including a private beach, 10 outdoor tennis courts, and complimentary bicycles. 3 outdoor swimming pools are on site along with a hot tub. Other recreational amenities include a sauna and a 24-hour fitness center.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "Excellent resort" - "The best property in the Keys. We loved it!" - "Probably the 2nd best resort I have stayed at in the Keys. Highly recommend! Lots of things to do in the resort such as pool, kayaking, paddle boarding, and bars. We also went fishing under the bridge near by and caught some nice fish! You can rent a boat at the resort but we didn’t as it wasn’t necessary since most boats came to the bridge to fish also. Had a great time and everyone in the area was very kind. "

Casa Morada
Hotel
136 Madeira Road, Islamorada, FL, FL 33036, USA

Located in Islamorada, a 10-minute walk from Upper Matecumbe Key, Casa Morada has accommodations with free bikes, free private parking, an outdoor swimming pool and a garden. With a terrace, the 5-star hotel has air-conditioned rooms with free WiFi, each with a private bathroom. The hotel provides a hot tub and luggage storage space. At the hotel, every room has a closet. Rooms come with a coffee machine, while some rooms include a balcony and others also feature sea views. The rooms in Casa Morada are equipped with a flat-screen TV and free toiletries. Guests at the accommodation can enjoy a buffet breakfast. Theater of the Sea on Islamorada is 2.3 miles from Casa Morada, while Windley Key is 2.9 miles from the property. Miami International Airport is 75 miles away.

Guest Reviews:

- "Best hidden gem in the keys" - "Overall great stay. Comfortable beds and room. And right next to where we wanted to be." - "Amazing place" - "A wonder escape from Miami" - "CLASSIC ESTABLISHMENT A MUST VISIT" - "perfect in every way" - "We found a hidden gem at Casa Morada. We plan to go again next year." - "Excellent!" - "It was a very nice stay. The reception was very helpful. Great outdoor area." - "Beautiful and relaxing environment"

Amara Cay Resort
Resort
80001 Overseas Hwy, Islamorada, FL, 33036, USA

On private beach with outdoor pool, near Bud n' Mary's Dive Center
At Amara Cay Resort, spend the day on the private sand beach where you can enjoy snorkeling. Then return for a meal at one of the resort's 2 restaurants.
Change of towels is available on request.
Amara Cay Resort offers 110 air-conditioned accommodations with safes and coffee/tea makers. Each accommodation is individually furnished and decorated. Pillowtop beds feature Egyptian cotton sheets, down comforters, and premium bedding. Flat-screen televisions are featured in guestrooms.

Bathrooms include bathtubs or showers, bathrobes, complimentary toiletries, and hair dryers. Business-friendly amenities include desks and desk chairs, as well as phones; free local calls are provided (restrictions may apply). Additionally, rooms include irons/ironing boards and blackout drapes/curtains. Hypo-allergenic bedding and change of towels can be requested. Housekeeping is provided daily.


Recreational amenities at the resort include a private beach, an outdoor pool, and a fitness center.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "The resort itself is amazing, just one thing that they need to work on is with the restaurant menu specifically breakfast " - "I would recommend this hotel the staff is super friendly. The hotel is clean. Q at the front desk made our stay at the hotel extra special. She was outstanding. I would definitely stay here again. " - "We had a great stay. The resort is so relaxing from the ocean swim to the pool. The resort staff was super friendly and I am already planning with my friends a time we can get back to enjoy for more!"

Islander Resort
Resort
82100 Overseas Highway, Islamorada, FL, FL 33036, USA

A tranquil and relaxing retreat directly on the beach in the Florida Keys, this property offers spacious accommodations equipped with microwaves and refrigerators and easy access to attractions and activities. Relax and enjoy beautiful views from fully furnished private porches or lanais. Spend the afternoon lounging by the Islander's 2 on-site swimming pools. Enjoy on-site dining at Beachside Bar and Grill. Easily discover a variety of activities only minutes from the Islander Resort, including snorkeling and scuba diving. Enjoy deep-sea fishing, sailing or browsing the local shops, also only a short distance away.

Guest Reviews:

- "We enjoyed our stay room was beautiful clean and wonderful staff. We enjoyed all the amenities that were offered! We" - "Private, secluded, uncrowded, and dog-friendly!" - "Stay longer" - "The location was perfect and close to restaurants in the area. Hope to return !" - "Will definitely return!" - "A relaxing stay with polite and attentive staff. The location is perfect for restaurants and attractions within walking" - "Relaxing time at a beautiful smallish resort on the beach!"

Islander Resort
Hotel
82100 Overseas Highway, Islamorada, FL, 33036, USA

Family-friendly beachfront location with 2 outdoor pools
At Islander Resort, spend the day on the private sand beach where you can enjoy volleyball. Then return for a meal at one of the hotel's 3 restaurants.
Islander Resort offers 114 accommodations, which are accessible via exterior corridors and feature safes and complimentary bottled water. Rooms open to lanais. Beds feature premium bedding. 50-inch Smart televisions come with cable channels. Bathrooms include bathtubs or showers, bathrobes, slippers, and complimentary toiletries.

Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include desks and desk chairs, as well as phones; free local calls are provided (restrictions may apply). Additionally, rooms include coffee/tea makers and hair dryers. Housekeeping is provided daily.


A private beach and complimentary bicycles are featured at the hotel. 2 outdoor swimming pools are on site along with a 24-hour fitness center.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "Loved this resort !!!!!!!! " - "A great experience" - "This amazing, family-owned resort checks all the boxes! Gorgeous grounds, fantastic food, superb service, beautifully appointed rooms - each with your own large, very private lanai and a fridge/freezer big enough to help with food & beverage costs. Two perfect pools, a large hot-tub, & splash pad, private dock, onsight snorkel excursions, extensive private beach, separate & charming wedding venue, and a relaxed vibe that just permeates everything. And, pet friendly as well."

Amara Cay Resort
Hotel
80001 Overseas Highway, Islamorada, FL, FL 33036, USA

This beachfront hotel is located in Islamorada, Florida and features transfer services within 3.7 mi from the property. WiFi is included in the resort fee. Guests can relax on beachside hammocks or enjoy the outdoor pool at Amara Cay Resort. An on-site fitness center is available, as well as a meeting space. A flat-screen TV, work desk, and safety deposit box comes standard in every guestroom. Bicycle rentals and luggage storage are offered on site. Sample a custom cocktail at the Tiki Bar or experience Amara Cay Resort’s restaurant, ReelCatch. The History of Diving Museum is 3 mi away. Guests will be 8 minutes’ drive from Anne’s beach. Windley Key Fossil Reef Geological State park is 8 minutes’ drive.

Guest Reviews:

- "Good price, beautiful grounds" - "Stunning stunning" - "Excellent" - "We had such a beautiful family vacation at Amara Cay we will definitely be returning." - "The best place for relax and romantic" - "Lovely staycation in Islamorada!" - "Had a great stay. Thank you" - "Amazing" - "Beautiful place and location. Great pool and pool bar!" - "Relaxing and exactly what we needed" - "The resort was great. Room service disappointed as they wouldn't report left items."

La Siesta Resort & Villas
Resort
80241 Overseas Highway, Islamorada, FL, 33036, USA

Beachfront, with outdoor pool
At La Siesta Resort & Villas, hit the private sand beach, relax by an outdoor pool, or spend the day at a marina.
Housekeeping is available on request.
La Siesta Resort & Villas offers 55 air-conditioned accommodations, which are accessible via exterior corridors and feature safes and coffee/tea makers. Each accommodation is individually decorated. Pillowtop beds feature Egyptian cotton sheets and premium bedding. Accommodations at this 4-star resort have kitchenettes with refrigerators and microwaves. Bathrooms include shower/tub combinations, designer toiletries, complimentary toiletries, and hair dryers.

Premium cable television is provided. Business-friendly amenities include desks, desk chairs, and phones. Additionally, rooms include irons/ironing boards and ceiling fans. Hypo-allergenic bedding and change of towels can be requested. Housekeeping is provided on request.


A private beach and a marina are featured at the resort. Other recreational amenities include an outdoor pool.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "Good " - "We had a double room (upstairs and downstairs) rented on the south side of property which was very nice. Big spaces, big balcony with some view of the water. I didn’t pay attention enough but assume there would be a place to swim on beach there. There isn’t. Everything is close to do anything you want to do though and had a great time. The only complaint that I had is that there is no dishes in the kitchenettes." - "Overall the Property is very nice. COVID makes some things of course difficult ....like meeting new friends. Very Clean. The continental breakfast could have been handled a bit better more hospitality."

La Siesta Resort & Villas
Hotel
80241 Overseas Highway, Islamorada, FL, FL 33036, USA

Just off the Overseas Highway and in front of the ocean, this Islamorada hotel offers an on-site marina. The beachfront hotel features an outdoor pool. WiFi is included in the resort fee. The suites and cottages at La Siesta Resort & Villas are equipped with a cable TV and air conditioning. On site, SIDECAR bar serves light fares, beer, and wine daily. Activities such as boating, fishing, jet skiing and snorkeling can be arranged. The on-site marina offers both gulf-side and ocean-side slips while non-motorized watersports equipment and bicycles are provided for guests' use. Theater of the Sea is 3.7 mi away from the accommodations while Anne's Beach is located 6.7 mi away.

Guest Reviews:

- "A piece of paradise." - "Would not have wanted to stay anywhere but at La Siesta!" - "Wish we could have stayed, hope to go again." - "Absolutely Perfect" - "Tropical vacation in the US, we loved it!" - "A great location with exceptional rooms that exceeded my expectations" - "We had a wonderful stay in a beautiful comfortable clean cabana." - "I’m very happy with the Resort" - "Great location with amazing ocean views."

The Islands of Islamorada
Villa
82779 Old Hwy, Islamorada, FL, 33036, USA

While you're here, you can enjoy all the comforts of home and more, including free WiFi and a Smart TV, as well as Netflix and a coffee/tea maker. Other amenities include designer toiletries, premium bedding, a pillowtop bed, and towels.

Guest Reviews:

- "We came the Labor Day weekend, to celebration two birthdays. It was a first for our family and we were pleasantly amazed by the property and all its amenities. We kayaked, sailed, played pickleball, biked and had a lot of fun overall. Our elderly mother was able to very comfortably relax inside, while enjoying the breathtaking views of the ocean from our balcony. We travel internationally several times a year,and this was one of our most relaxed vacations! But most noteworthy is the staff...they were all very attentive to our needs, super responsive and always with a smile. This was a top notch weekend, and we will absolutely be back. Special thanks to Mary at the front desk, who was the perfect host, very helpful with our elderly mother and so lovely! And Emanuel at the kayak stand who was always helpful and ready to assist."

Bayside Villas by Islander Resort
Resort
81450 Overseas Highway, Islamorada, FL, FL 33036, USA

Located on the waters of the Florida Bay, the Islander Bayside Resort is less than 5 minutes’ walk from the beach. This resort features a kitchen in every townhouse and an outdoor pool. A flat-screen TV is included in every guest townhouse of this Islamorada resort and all units have free WiFi and laundry facilities. Kitchens offer a microwave, refrigerator and an oven. Bicycle rental is possible on site and various water sport activities are located nearby. There are various dining options less than 1 mi from this resort and Windley Key Fossil Reef Park is 5 minutes’ drive away. Long Key is 15 minutes’ drive from the property. This hotel provides laundry valet service only.

Guest Reviews:

- "Shuttle to other resort was great" - "Excellent Value, would definitely revisit" - "Will stay again...great for families dn walking distance to some great spots." - "Amazing place" - "Amazing Stay in a beautiful, clean and friendly place!" - "Beautiful place, very cosy" - "Quick, nice stay!" - "Brand new villa on a serene peaceful location with beautiful view over the gulf- great for watching sunsets!" - "Saved by Alice"

Pineapple Beach by Florida Keys Luxury Rentals
House
130 Aregood Lane, Islamorada, FL, 33036

This smoke-free vacation home features a private beach, multilingual staff, and free self parking. WiFi in public areas is free. The vacation home boasts a private pool and offers free WiFi and a kitchen. Guests can appreciate conveniences like 4 bathrooms and a dining area, and other amenities include a refrigerator and a microwave.

Amenities:

Air Conditioner • Bedding/Linens • Kitchen • Pool • Internet • Private Pool

Anglers Reef Paradise
House
110 Anglers Way 110, Islamorada, FL, FL 33036, USA

Just a 6-minute walk from Windley Key and 0.8 miles from Theater of the Sea on Islamorada, Anglers Reef Paradise features accommodations in Islamorada, with pool with a view and a garden. This property offers access to a terrace, free private parking, and free Wifi. Outdoor seating is also available at the vacation home. The air-conditioned vacation home consists of 2 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a walk-in shower and a hair dryer. A flat-screen TV with streaming services and DVD player, as well as a CD player are available. For added privacy, the accommodation features a private entrance. During warmer months, you can make use of the barbecue facilities and eat on the private balcony. Guests at Anglers Reef Paradise will be able to enjoy activities in and around Islamorada, like cycling and fishing. Snorkeling and diving can be enjoyed nearby, while a bicycle rental service and a private beach area are also available on-site. Upper Matecumbe Key is 3.4 miles from the accommodation, while Pigeon Key is 10 miles from the property. Miami International Airport is 71 miles away.

Guest Reviews:

- "Perfect location, very comfortable stay in beautiful surroundings" - "Great experience" - "We had a great time, great facilities… no need to go out." - "Whether the sun shines or the breezes blow, we know we have now found the perfect place to relax and recharge." - "Fabulous pool on site and perfect location for exploring all of the Florida Keys" - "A great, beautiful, spacious, well furnished house in a nice community with nice views of the ocean"

Chesapeake Beach Resort
Hotel
83409 Overseas Hwy, Islamorada, FL, 33036, USA

Hotel on the beach, with 2 outdoor pools
At Chesapeake Beach Resort, you can relax at one of the 2 outdoor swimming pools, play on the private white sand beach, or spend the day at a marina.
Chesapeake Beach Resort offers 60 air-conditioned accommodations, which are accessible via exterior corridors and feature coffee/tea makers and designer toiletries. Beds feature pillowtop mattresses. 43-inch flat-screen televisions come with cable channels. Bathrooms include showers, complimentary toiletries, and hair dryers.

This Islamorada hotel provides complimentary wireless Internet access, with a speed of 100+ Mbps (good for 1–2 people or up to 6 devices). Business-friendly amenities include phones along with free local calls (restrictions may apply). Additionally, rooms include irons/ironing boards and ceiling fans. Housekeeping is offered daily and hypo-allergenic bedding can be requested.


A private beach, a marina, and complimentary bicycles are featured at the hotel. 2 outdoor swimming pools are on site.

Children under 16 years old are not allowed in the swimming pool without adult supervision.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "Beautiful property and helpful staff." - "Easy check in, property and room very clean. " - "Great Waterview" - "It was a perfect spot close to all we wanted to do. Will definitely be back!" - "Great views, spacious and clean room, and convenient location to drive to restaurants and other Keys! The property was safe and quiet. There were kayaks, paddle boards, and life jackets available as well as boat rentals on site. The one downside was the breakfast was very limited on options but it was available for 6-11 am. Overall a great value for a beautiful spot!"

The Islands of Islamorada
Hotel
82779 Old Highway, Islamorada, FL, FL 33036, USA

Located in Islamorada, 1.1 miles from Upper Matecumbe Key, The Islands of Islamorada provides accommodations with free bikes, free private parking, an outdoor swimming pool and a fitness center. The property has a private beach area and water sports facilities, as well as a terrace and a bar. The hotel features a hot tub, room service and free WiFi throughout the property. Some rooms are equipped with a kitchen with a fridge, a dishwasher and an oven. The hotel has a playground. Guests at The Islands of Islamorada will be able to enjoy activities in and around Islamorada, like snorkeling. Theater of the Sea on Islamorada is 1.7 miles from the accommodation, while Windley Key is 2.3 miles away. Miami International Airport is 74 miles from the property.

Guest Reviews:

- "A tropical oasis" - "Beautiful and quiet resort, perfect for a wedding anniversary weekend" - "A bunch of fun with friends at a beautiful place"

Hadley Resort and Marina
Hotel
82749 Overseas Hwy, Islamorada, FL, 33036, USA

Family-friendly beachfront location with outdoor pool
At Hadley Resort and Marina, hit the private sand beach, relax by an outdoor pool, or spend the day at a marina.
Housekeeping is available on request.
Hadley Resort and Marina offers 37 air-conditioned accommodations, which are accessible via exterior corridors and feature coffee/tea makers and hair dryers. Rooms open to furnished balconies or patios. Each accommodation is individually furnished and decorated. Beds feature premium bedding. Premium satellite television is provided. Bathrooms include shower/tub combinations and complimentary toiletries.

Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include phones; local and long-distance calls are complimentary (restrictions may apply). Additionally, rooms include irons/ironing boards and blackout drapes/curtains. Change of towels and change of bedsheets can be requested. Housekeeping is provided on request.


A private beach, a marina, and complimentary bicycles are featured at the hotel. Other recreational amenities include an outdoor pool.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "Very cute hotel. " - "Very well done" - "The area is great " - "Great stay, good location, nice spacious updated rooms " - "Very clean, love the kitchen. And quite! Pool awesome! " - "Only complaint is 8AM breakfast should occur earlier. Great, friendly staff " - "Friendly staff. Nice room." - "I can't say enough good things about our stay! We rented a 2 bedroom unit. So spacious, views were breathtaking. Quite, had everything we needed. Breakfast in the morning till 10:30. Check out 11. Thomas manager offered so many suggestions to our questions ."

Islamorada Paradise Overlooking the Fabulous Florida Bay.
Apartment
88540 Overseas Highway, Tavernier, FL, FL 33070, USA

Featuring a tennis court, Islamorada Paradise Overlooking the Fabulous Florida Bay. Features accommodations in Tavernier. Among the facilities at this property are an elevator and bicycle parking, along with free Wifi throughout the property. The property provides barbecue facilities and parking on-site. Providing a balcony and sea views, the spacious apartment includes 3 bedrooms, a living room, flat-screen TV, an equipped kitchen, and 2 bathrooms with a shower. Towels and bed linen are provided in the apartment. The accommodation is non-smoking. Guests can also relax in the garden, next to the infinity pool, on the sun terrace, or in the shared lounge area. Windley Key is 3.2 miles from the apartment, while Upper Matecumbe Key is 6.5 miles away. Miami International Airport is 68 miles from the property.

Guest Reviews:

- "What a wonderful place to spent to get away from it all!" - "Great location, clean and well equipped; highly recommended."

Fisher Inn Resort & Marina
Hotel
84951 Overseas Hwy, Islamorada, FL, 33036, USA

Family-friendly fun on the beach, with outdoor pool
At Fisher Inn Resort & Marina, relax by an outdoor pool or hit the private sand beach where you can enjoy snorkeling.
Housekeeping is available on request.
Fisher Inn Resort & Marina offers 22 air-conditioned accommodations with coffee/tea makers and irons/ironing boards. Each accommodation is individually furnished and decorated. Beds feature premium bedding. Refrigerators and microwaves are provided. Bathrooms include shower/tub combinations and complimentary toiletries.

Guests can surf the web using the complimentary wireless Internet access (speed: 50+ Mbps). Premium cable television is provided. Hair dryers, change of towels, and change of bedsheets can be requested. Housekeeping is provided on request.


A private beach and complimentary bicycles are featured at the motel. Other recreational amenities include an outdoor pool.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "Excellent " - "All fine, we like it" - "The staff was very friendly and helpful." - "It was a great place to stay " - "Lots of amenities " - "Beautiful location. We arrived late but still had to pay the resort fee. Next morning was cold and blustery and we weren't able to use any of the kayaks, pool etc" - "Staff was friendly and helpful. Property and room was clean. I would stay again." - "it was a pleasure staying with them!"

Key Lime Cottage in the heart of Islamorada
House
76777 Overseas Highway, Islamorada, FL, FL 33036

Key Lime Cottage in the heart of Islamorada offers accommodations in Islamorada, 1.6 miles from Sea Oats Beach and 5.3 miles from Upper Matecumbe Key. This property offers access to a terrace and free private parking. Outdoor seating is also available at the vacation home. This air-conditioned 2-bedroom vacation home comes with a seating area, a satellite flat-screen TV, and a fully equipped kitchen with an oven. Towels and bed linen are provided in the vacation home. For added privacy, the accommodation features a private entrance. Guests can enjoy the outdoor swimming pool and garden at Key Lime Cottage in the heart of Islamorada. Theater of the Sea on Islamorada is 7.8 miles from the accommodation, while Windley Key is 8.4 miles away. Key West International Airport is 74 miles from the property.

Guest Reviews:

- "If you can sustain in a cottage style design, then your stay will be worth it."

Sunset Inn
Hotel
82200 Overseas Hwy, Islamorada, FL, 33036-3637, USA

Hotel in Islamorada with free parking
An outdoor pool, free use of bicycles, and a garden are available at this smoke-free hotel. Free WiFi in public areas and free self parking are also provided. Additionally, barbecue grills, a picnic area, and a front-desk safe are onsite.
Sunset Inn offers 30 air-conditioned accommodations, which are accessible via exterior corridors and feature laptop-compatible safes and coffee/tea makers. Flat-screen televisions come with cable channels and Netflix.

Bathrooms include showers, bidets, complimentary toiletries, and hair dryers. Guests can surf the web using the complimentary wireless Internet access. Housekeeping is provided daily.


Recreational amenities at the hotel include an outdoor pool and complimentary bicycles.

Guest Reviews:

- "Friendly staff and very clean. Great value! " - "Have stayed here the last 3 years and the staff is friendly, the pool is heated and it’s location is great " - "This may be an old hotel, but well taken care of, clean, nice pool, updated bathroom… will stay here again! " - "My room was very clean and huge, and the heated pool was great after a long day on the road! My only issue was with the traffic as it’s next to a very busy road, so I barely got some sleep, but other than that it’s a great location and other guests didn’t seem too bothered by the noise so maybe it’s just me!"

EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS
House
87200 Overseas Highway, Islamorada, FL, FL 33036, USA

EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS in Islamorada provides accommodations with a private beach area, an outdoor swimming pool, and a garden. There's a private entrance at the vacation home for the convenience of those who stay. The vacation home features rooms with air conditioning, free private parking, and free Wifi. The vacation home provides guests with a terrace, a seating area, satellite flat-screen TV, a fully equipped kitchen with a dishwasher and an oven, and a private bathroom with walk-in shower and a hair dryer. A microwave, a toaster, and fridge are also available, as well as a coffee machine. At the vacation home, every unit is equipped with bed linen and towels. There is an on-site bar, and during warmer months you can make use of the barbecue facilities. You can play tennis at EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS. The vacation home has a picnic area where you can spend the day outdoors. Windley Key is 2.4 miles from the accommodation, while Theater of the Sea on Islamorada is 3 miles from the property. Miami International Airport is 70 miles away.

Amenities:

Balcony/Terrace • Internet • Bar • View • Ocean View • Barbecue/Outdoor Cooking • Tv • Sports/Activities • Fireplace/Heating • Security/Safety • Entertainment • Oceanfront

Drop Anchor
Hotel
84959 Overseas Highway, 222, Islamorada, FL, 33036, USA

Art Deco hotel with a nearby private beach and an outdoor pool
Along with an outdoor pool, this hotel has coffee/tea in a common area and a business center. Free WiFi in public areas and free self parking are also provided. Additionally, free use of bicycles, wedding services, and a garden are onsite.
Limited housekeeping is available.
Drop Anchor offers 18 air-conditioned accommodations with coffee/tea makers and hair dryers. Each accommodation is individually furnished and decorated. Beds feature premium bedding. Flat-screen televisions come with premium cable channels.

Bathrooms include showers and complimentary toiletries. This Islamorada hotel provides complimentary wireless Internet access. Additionally, rooms include irons/ironing boards and ceiling fans. Housekeeping is provided daily.


Recreational amenities at the hotel include an outdoor pool and complimentary bicycles.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "We chose the property as a last minute option and because of its proximity to our fishing guide’s marina. We didn’t expect as nice a pool and beach area and the option of using the hotels boat ramp and moorings. The bright colors added to the beach ambience. While the rooms are simple and our bathroom was small, everything was functional and clean. The highlight was the personable and very helpful manager." - "Very Nice location and spectacular view. Sandy Beach area...no shoes required. I was very satisifed with everything about Drop Anchor. Our accomadations were a quaint bungalow with 2 bedrooms, living room, dining and kitchen. Bath nice too. Clean, great view right out our windows with a nice private patio There is even a boat launch here and private dock for your boat. Just offshore in the Islamorada Sand Bar snorkeling, fishing and just hanging out. here you are close to Theatre on the Sea, Robbies (A MUST FOR Lunch or Dinner...order "MAHI"), Abel's Tackle Box, Wahoo Bar n Grill and too many Marines and other great dining. The Owner/Manager is the most helpful and knowlegable guy and his insight is worth the price of your stay alone. Only regret is we should have stayed way longer......"

Anglers Reef Vacation Rental
Villa
109 Anglers Way, Islamorada, FL, FL 33036, USA

Just a 5-minute walk from Windley Key and 0.7 miles from Theater of the Sea on Islamorada, Anglers Reef Vacation Rental features accommodations in Islamorada with barbecue facilities. This property offers access to a balcony and free private parking. The pool features a fence and garden views. With free Wifi, this 2-bedroom villa offers a cable flat-screen TV, a washing machine, and a fully equipped kitchen with kitchenware. The accommodation is non-smoking. Guests at the villa will be able to enjoy activities in and around Islamorada, like fishing and canoeing. Snorkeling and cycling can be enjoyed nearby, while a private beach area and water sports facilities are also available on-site. Upper Matecumbe Key is 3.4 miles from Anglers Reef Vacation Rental, while Pigeon Key is 10 miles from the property. Miami International Airport is 71 miles away.

Amenities:

Sports/Activities • Balcony/Terrace • Parking • Ocean View • Guest Services • Oceanfront • Private Beach • Pool • Security/Safety • Wellness Facilities • Air Conditioner • Barbecue/Outdoor Cooking

Pelican Cove Resort & Marina
Hotel
84457 Overseas Highway, Islamorada, FL, 33036, USA

Ocean-view hotel with a poolside bar, near Windley Key Fossil Reef Geological State Park
At Pelican Cove Resort & Marina, hit the private sand beach, relax by an outdoor pool, or spend the day at a marina.
Pelican Cove Resort & Marina offers 63 accommodations, which are accessible via exterior corridors and feature safes and coffee/tea makers. Rooms open to balconies. These individually decorated and furnished accommodations have separate dining areas. LCD televisions come with premium cable channels. Bathrooms include shower/tub combinations, complimentary toiletries, and hair dryers.

This Islamorada hotel provides complimentary wireless Internet access. Business-friendly amenities include desks and phones. Additionally, rooms include irons/ironing boards and blackout drapes/curtains. Housekeeping is provided daily.


A private beach and a marina are featured at the hotel. Other recreational amenities include an outdoor pool.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "We had a great time in paradise. We’ll hopefully be coming back next year for a longer stay." - "So not what we were expecting. Want my money back !" - "My boyfriend and I stayed here for a weekend get away. We love the private beach and the adult vibe yet family friendly. Great staff who did everything possible to make our stay wonderful! We can’t wait to come back!" - "This property was perfect for our weekend getaway. Outside of the unit accommodations, the amenities were great."

Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water views!
House
Islamorada, FL, USA

Offering a spa and wellness center and a garden, Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water views! in Islamorada is close to Upper Matecumbe Key and History of Diving Museum. This vacation home provides air-conditioned accommodations with a balcony. The vacation home features parking on-site, an outdoor swimming pool, and a 24-hour front desk. With free Wifi, this 3-bedroom vacation home offers a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. The accommodation is non-smoking. Theater of the Sea on Islamorada is 2.1 miles from the vacation home, while Windley Key is 2.7 miles from the property. Miami International Airport is 74 miles away.

Amenities:

Pool • Sports/Activities • Guest Services • Air Conditioner • Wellness Facilities • Security/Safety • View • Breakfast • Parking • Other • Spa • Internet

Pines & Palms Resort
Hotel
80401 Old Hwy, Islamorada, FL, 33036, USA

Beachfront, with outdoor pool
At Pines & Palms Resort, hit the private sand beach, relax by an outdoor pool, or spend the day at a marina.
Pines & Palms Resort offers 26 air-conditioned accommodations with coffee/tea makers and hair dryers. These individually decorated and furnished accommodations have separate sitting areas. Beds feature premium bedding. Accommodations at this 3-star hotel have kitchens with full-sized refrigerators/freezers, stovetops, microwaves, and cookware/dishes/utensils.

Guests can surf the web using the complimentary wireless Internet access. Flat-screen televisions come with premium cable channels. Additionally, rooms include irons/ironing boards and complimentary toiletries. Housekeeping is provided daily.


A private beach and a marina are featured at the hotel. Other recreational amenities include an outdoor pool.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "This villa was spectacular! Beds…awesome. Showers…awesome. View….best ever." - "The property and room very clean, only down fall was that the tiki bar was not always open" - "Beautiful location easy to stay, relaxing atmosphere, convenient" - "Awesome location, property and people. Will definitely be back!" - "My family and I usually travel somewhere warm just after Christmas and this time we decided on the Fl Keys. Staying at this place was wonderful. My son enjoyed the heated pool and as an amateur outdoor photographer, I was astounded and so very pleased with all the waterfowl that I was able to photograph on the beach without ever leaving the balcony. The beds were very comfortable (a must in my book), the staff was very pleasant, and the property (albeit with a slightly dated kitchen....but you are renting it, not buying it) was well maintained and immaculate, including the beaches which were raked every morning by the landscaping crew. Next time we are in the keys, we will try to stay here at the exact same villa once again."

Ocean View Penthouse Retreat amenities: tennis court heated Pool Vista Key Two
Apartment
Islamorada, FL, USA

Offering massage services, Ocean View Penthouse Retreat amenities: tennis court heated Pool Vista Key Two provides accommodations in Islamorada. The air-conditioned accommodation is a 1-minute walk from Sea Oats Beach. Upper Matecumbe Key is 7.7 miles away and Theater of the Sea on Islamorada is 10 miles from the apartment. Providing a balcony with sea views, this apartment also provides guests with a cable TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 3 bathrooms with a bath and a hair dryer. The accommodation is non-smoking. Guests can also relax in the garden. Windley Key is 11 miles from the apartment, while Pigeon Key is 21 miles away. Key West International Airport is 71 miles from the property.

Amenities:

Barbecue/Outdoor Cooking • View • Guest Services • Air Conditioner • Other • Pet Friendly • Accessibility • Security/Safety • Sports/Activities • Parking • Pool • Wellness Facilities

Casa Morada
Hotel
136 Madeira Road, Islamorada, FL, 33036, USA

Adults-only beach hotel with outdoor pool
At Casa Morada, relax by an outdoor pool or hit the nearby beach where you can enjoy kayaking.
Casa Morada offers 16 accommodations with DVD players and minibars. Rooms open to balconies or patios. These individually decorated and furnished accommodations have separate sitting areas. Beds feature premium bedding. Flat-screen televisions come with cable channels. Bathrooms include bathrobes, designer toiletries, complimentary toiletries, and hair dryers.

Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include safes and phones; free local calls are provided (restrictions may apply). In-room massages and irons/ironing boards can be requested. Housekeeping is provided daily.


Recreational amenities at the hotel include an outdoor pool and complimentary bicycles.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "quiet, relaxing, great hospitality and perfect location to walk or bike to everything needed" - "Nice little hidden gem!" - "Had a great time" - "accommodations, grounds, pool.... all perfectly lovely, and the thoughtful nighttime thunder and lightning show was over the top. loved the place. would suggest you for a wonderful break from the rat world to anyone. thank you so much for the needed respite." - "This place is beautiful! Can’t wait to go back! Hazel was so awesome when we checked in and Yoga on the water was just the icing on the cake, thank you Lauren! A perfect weekend away. "

Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location
Villa
Islamorada, FL, USA

Just a 12-minute walk from Upper Matecumbe Key and 0.7 miles from History of Diving Museum, Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location features accommodations in Islamorada with a garden. This villa offers air-conditioned accommodations with a balcony. The villa features parking on-site, an outdoor swimming pool, and a 24-hour front desk. With free Wifi, this 3-bedroom villa provides a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. The accommodation is non-smoking. Theater of the Sea on Islamorada is 2.1 miles from the villa, while Windley Key is 2.7 miles away. Miami International Airport is 74 miles from the property.

Amenities:

Sports/Activities • Wellness Facilities • Air Conditioner • Other • View • Internet • Parking • Pool • Breakfast • Guest Services • Accessibility • Security/Safety

Bayside Villas by Islander Resort
Hotel
81450 Overseas Highway, Islamorada, FL, 33036, USA

Beach location and outdoor pool
Spend the day on the nearby beach where you can enjoy sailing. Then return to Bayside Villas by Islander Resort for a meal at one of the hotel's 3 restaurants.
Weekly housekeeping is available.
Bayside Villas by Islander Resort offers 25 accommodations with safes and complimentary bottled water. Rooms open to furnished balconies. Accommodations have separate sitting areas and are furnished with queen sofa beds and dining tables. Pillowtop beds feature premium bedding. Accommodations at this 3.5-star hotel have kitchens with full-sized refrigerators/freezers, stovetops, microwaves, and separate dining areas. Bathrooms include bathtubs or showers, designer toiletries, complimentary toiletries, and hair dryers.

This Islamorada hotel provides complimentary wireless Internet access. 55-inch LCD televisions come with cable channels. Additionally, rooms include coffee/tea makers and ceiling fans. Hypo-allergenic bedding, change of towels, and change of bedsheets can be requested. Housekeeping is provided daily.


Recreational amenities at the hotel include an outdoor pool.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "The property was clean and well taken car of." - "Nice quiet place on the bayside! Excellent place. Clean. Rooms could be updated, but that wasn’t any concern for me. I loved it! Had to pool to ourselves! Will stay here again!" - "Great place with incredible view of the bay." - "Loved the location. Near many restaurants and local shopping. They have a golf cart that will drive you within a mile or so of the resort. We tried to take it, but it took too long to come (waited 30 min). Kitchen cook ware and utensils were sparse. Tried to contact the property through the VRBO app to see if we could make minor change to our dates, but never received a response. Other than those 2 minor things, great place!!"

Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Villa
Islamorada, FL, USA

Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable offers accommodations in Islamorada, a 12-minute walk from Upper Matecumbe Key and 2.1 miles from Theater of the Sea on Islamorada. This villa features air-conditioned accommodations with a balcony. The villa offers parking on-site, an outdoor swimming pool, and a 24-hour front desk. With free Wifi, this 3-bedroom villa provides a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. The accommodation is non-smoking. A children's playground is also available at the villa, while guests can also relax in the garden. Windley Key is 2.7 miles from Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable, while Pigeon Key is 13 miles away. Miami International Airport is 74 miles from the property.

Amenities:

Security/Safety • Guest Services • Air Conditioner • Breakfast • Parking • Other • View • Wellness Facilities • Internet • Child Friendly • Sports/Activities • Pool

The Caribbean Resort
Hotel
117 Carroll St, Islamorada, FL, 33036, USA

Waterfront hotel with a marina and an outdoor pool
Along with a marina, this hotel has an outdoor pool and a hot tub. Other amenities include free use of bicycles, laundry facilities, and wedding services.
The Caribbean Resort offers 14 air-conditioned accommodations with washers/dryers and coffee/tea makers. Rooms open to balconies or patios. These individually decorated and furnished accommodations have separate sitting areas. Beds feature premium bedding. Accommodations at this 3.5-star hotel have kitchens with full-sized refrigerators/freezers, stovetops, microwaves, and separate dining areas.

Bathrooms include showers, complimentary toiletries, and hair dryers. LED televisions come with premium cable channels. Additionally, rooms include irons/ironing boards and ceiling fans. Housekeeping is provided daily.


A marina and complimentary bicycles are featured at the hotel. An outdoor pool and a hot tub are on site.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "The grounds were beautiful and well kept. the staff was friendly and helpful. Everything needed for a wonderful stay was included. It is a beautiful resort and The only improvement I would recommend would be to get a larger screen TV." - "This place is like a dream. There are fancier places on the island but the vibe here was so amazing. They really feel like they are working extra hard to create something special. The only thing we were sad about was the bed was pretty firm but overall I would give this a 10 out of 10 experience "

Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location
Villa
Islamorada, FL, USA

Just a 12-minute walk from Upper Matecumbe Key and 0.7 miles from History of Diving Museum, Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location features accommodations in Islamorada with a spa and wellness center. This villa provides air-conditioned accommodations with a balcony. The villa offers parking on-site, an outdoor swimming pool, and a 24-hour front desk. With free Wifi, this 3-bedroom villa features a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. The accommodation is non-smoking. A children's playground is also available at the villa, while guests can also relax in the garden. Theater of the Sea on Islamorada is 2.1 miles from Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location, while Windley Key is 2.7 miles from the property. Miami International Airport is 74 miles away.

Amenities:

Pool • Sports/Activities • Security/Safety • Other • View • Wellness Facilities • Spa • Air Conditioner • Guest Services • Breakfast • Parking • Internet

Coconut Cove Resort and Marina
Hotel
84801 Overseas Highway, Islamorada, FL, 33036, USA

Family beach fun and outdoor pool
Guests at this beach hotel will appreciate convenient onsite amenities such as a children's pool and barbecue grills.
Housekeeping is available on request.
Coconut Cove Resort and Marina offers 20 accommodations, which are accessible via exterior corridors and feature coffee/tea makers and hair dryers. Rooms open to patios. 24-inch LCD televisions come with cable channels.

Refrigerators and microwaves are provided. Additionally, rooms include complimentary toiletries and ceiling fans. Irons/ironing boards and change of towels can be requested. Housekeeping is provided daily.


An outdoor pool and a children's pool are on site. Other recreational amenities include a fitness center.

Children under 18 years old are not allowed in the fitness facility without adult supervision.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "Very good 👍 " - "It was like being in paradise. Beautiful surroundings, helpful staff and was made to feel very welcome" - "Wonderful view" - "Wonderful place; everything is very nice there!" - "Personal , place and peaceful!!" - "If you are looking to stay at a high end luxury resort this is not the place for you. If you are looking to stay in a quiet, clean, family owned property that is trying to retain the historic charm and independent ownership of the keys, by all means stay here. We loved the staff, the natural state of the property, the 2 person jacuzzi in our room was well worth the extra money for the seasonal weather. Wish we had more time to relax on property and enjoy. Only thing missing was a tetherball court. Great bar and restaurant Oceanview right across the street. If you don't like cats, you are probably not a good person anyway, but also don't stay in the keys or this property. A highlight of our stay was getting to know "Stump" , "Sneaky Pete" and the other numerous super friendly cats that keep the property entertaining and pest free. Hope to return someday soon. Keep the keys free from development!"

Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location
Villa
Islamorada, FL, USA

Just a 12-minute walk from Upper Matecumbe Key and 0.7 miles from History of Diving Museum, Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location features accommodations in Islamorada with a spa and wellness center. This villa features air-conditioned accommodations with a balcony. The villa provides parking on-site, an outdoor swimming pool, and a 24-hour front desk. With free Wifi, this 3-bedroom villa offers a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. The accommodation is non-smoking. A children's playground is also available at the villa, while guests can also relax in the garden. Theater of the Sea on Islamorada is 2.1 miles from Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location, while Windley Key is 2.7 miles away. Miami International Airport is 74 miles from the property.

Amenities:

View • Sports/Activities • Pet Friendly • Parking • Guest Services • Security/Safety • Child Friendly • Breakfast • Other • Internet • Spa • Wellness Facilities

Treasure Harbor
Boat Rental
200 Treasure Harbor Dr, Islamorada, FL, 33036, USA

Hotel in Islamorada with free parking
This smoke-free hotel features an outdoor pool, free self parking, and free WiFi in public areas. Other amenities include a vending machine.
Housekeeping is available once per stay.
Treasure Harbor offers 6 air-conditioned accommodations with coffee/tea makers and hair dryers. These individually decorated accommodations have separate sitting areas. Beds feature premium bedding. 25-inch flat-screen televisions come with digital channels.

Bathrooms include showers and complimentary toiletries. This Islamorada hotel provides complimentary wireless Internet access. Housekeeping is offered once per stay and change of towels can be requested. Housekeeping is provided on a limited basis.


Recreational amenities at the hotel include an outdoor pool.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "Excellent location and beautiful serene place. " - "Excelente " - "Everything was great! Loved the porch to lookout on the water. We had a manatee come say hi! If you go kayaking we saw so much sea life. There was a shark and seq turtle swimming right beside us. It was beautiful to watch and relax. Everyone at the site were friendly and helpful!" - "Absolute top notch all around!! We loved it and only wished we booked longer. "

Hidden Gem Duplex in Heart of Islamorada Sleeps 8
House
82236 Overseas Highway, Islamorada, FL, 33036, USA

Just a 13-minute walk from Upper Matecumbe Key and 0.6 miles from History of Diving Museum, Hidden Gem Duplex in Heart of Islamorada Sleeps 8 features accommodations in Islamorada with a garden. This vacation home offers air-conditioned accommodations with a patio. Theater of the Sea on Islamorada is 2.1 miles away and Windley Key is 2.7 miles from the vacation home. With free Wifi, this 4-bedroom vacation home features a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are available in the vacation home. For added privacy, the accommodation features a private entrance. Pigeon Key is 13 miles from the vacation home, while John Pennekamp State Park is 21 miles from the property. Miami International Airport is 74 miles away.

Amenities:

Child Friendly • Security/Safety • View • Fireplace/Heating • Internet • Parking • Air Conditioner

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Resort
84001 Overseas Hwy, Islamorada, FL, 33036, USA

Family-friendly beachfront location with 3 outdoor pools
Spend the day relaxing on Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort's private sand beach or at a marina before returning for a meal at one of the resort's 4 restaurants.
Housekeeping is available on request.
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort offers 214 accommodations, which are accessible via exterior corridors and feature safes and complimentary bottled water. Each accommodation is individually furnished and decorated. Refrigerators and coffee/tea makers are provided. Bathrooms include bathtubs or showers, complimentary toiletries, and hair dryers.

Guests can surf the web using the complimentary wireless Internet access. 37-inch flat-screen televisions come with cable channels. Housekeeping is provided on request.


A private beach, a marina, and complimentary bicycles are featured at the resort. 3 outdoor swimming pools are on site along with a 24-hour fitness center.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "We stayed for two nights in February. Great property and Italian restaurant" - "On its way back better then ever from before. Staff was amazing and so was the food and drink. Top notch" - "Awesome place, beautiful , lots to do , wish i could move there" - "It was a nice resort feel unlike any I have had in the keys" - "The entire staff was very friendly " - "Excellent and amazing property. I love this resort. Will be back"

Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location
House
Islamorada, FL, USA

Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location offers accommodations in Islamorada, a 12-minute walk from Upper Matecumbe Key and 2.1 miles from Theater of the Sea on Islamorada. This vacation home provides air-conditioned accommodations with a balcony. The vacation home offers parking on-site, a spa center, and a 24-hour front desk. With free Wifi, this 3-bedroom vacation home features a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. The accommodation is non-smoking. A children's playground is also available for guests at the vacation home. Windley Key is 2.7 miles from Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location, while Pigeon Key is 13 miles from the property. Miami International Airport is 74 miles away.

Amenities:

Breakfast • Parking • Wellness Facilities • Sports/Activities • Guest Services • Other • Security/Safety • Child Friendly • Air Conditioner • View • Internet • Spa

Topsider Resort
Condo
75500 Overseas Hwy, Islamorada, FL, 33036, USA

A short distance from scuba diving, snorkeling, and more, this beach condo lets you experience it all. Jump into your car and make short work of the 5-minute drive to Anne's Beach or the 3-minute drive to Robbie’s of Islamorada (and enjoy the property's convenient onsite parking in the meantime).

After you return, you can unwind at the private beach (enjoy the beach umbrellas!), chill by the heated pool with the sun loungers, or sip a drink in the hot tub; you may also like the garden. As for the great indoors, you can come inside and enjoy the free WiFi and TV.

As you settle into this 2-bedroom, 2-bathroom rental, you'll find a BBQ grill and climate-controlled air-conditioning. The kitchen is equipped with an oven, a stovetop, and a full-sized refrigerator/freezer, as well as a coffee maker, a microwave, and cookware. And there's access to laundry facilities, so you can even pack a bit lighter.

Guest Reviews:

- "Its a great choice for small families looking to relax. Heated pool and hot tub. on property beach access (gulf side). Kayaks and bikes to use. inside the dwelling, master bedroom w/ full bath, another bedroom w/ two twin beds, another full bath, full kitchen + kitchenette, and living room. Really pleased. " - "Was happy with our stay as I didn’t have high expectations of it being fancy or modern. We learned that a Topsider is kind of like a treehouse with its main support in the middle underneath which puts you 9-10ft up off the ground. There was some sagging around the outside edges of the structure causing gaps in the flooring and flex with walking around. We loved the simplicity and quietness of this place, the private little beach & dock. All our “neighbors” were kind & respectful with many having ownership in this 20 unit “resort”. Make sure you bring your own shampoo/cond. if you prefer to not use bar soap or dish soap. Hair dryers are also not supplied. The kitchen is well stocked w/dishes, utensils, pots & pans but need to bring your own salt, pepper, oil or anything to cook with. Check-in was easy & proactive communication was appreciated. The beds were quite firm for my liking and bathrooms very small. Good A/C to keep you comfortable. Didn’t use the pool or hot tub as they were sorta out of commission. Glad we got to stay here to end 2024 & start 2025!"

Waterfront Wonder
House
Islamorada, FL, USA

Waterfront Wonder is located in Islamorada, just a 9-minute walk from Sea Oats Beach and 7.6 miles from Upper Matecumbe Key. The vacation home has access to a restaurant. The vacation home offers an outdoor swimming pool, hot tub, and an elevator. Accommodation for disabled guests is also available at the property. Providing access to a balcony with pool views, the spacious air-conditioned vacation home consists of 6 bedrooms. Offering a terrace with sea views, this vacation home also features a satellite TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 6 bathrooms with a walk-in shower and a hair dryer. There's also a seating area and a fireplace. A children's playground is also available for guests at the vacation home. Theater of the Sea on Islamorada is 10 miles from Waterfront Wonder, while Windley Key is 11 miles from the property. Key West International Airport is 72 miles away.

Amenities:

Laundry • Wellness Facilities • Hot Tub • Restaurant • Guest Services • View • Security/Safety • Balcony/Terrace • Child Friendly • Sports/Activities • Pet Friendly • Wheelchair Accessible

Angler's Reef Resort by KeysCaribbean
House
84977 Overseas Highway, Islamorada, FL, 33036, USA

While you're here, you can enjoy all the comforts of home and more, including a full-sized refrigerator/freezer and an oven, as well as a stovetop and a dishwasher. Other amenities include hypo-allergenic bedding, laundry facilities, a freezer, and towels.

Guest Reviews:

- "Overall 4.5 stars. The house/villa itself needs a bit of checking up on like under the back deck and head the beat in a carpet nail on the stairs. Also the master suite backs into the edge of the property and you can hear the traffic outside very clearly all day+night, it was not the best for sleeping once people really hit the road in the early morning. The rest was great. Large beds and TVs, full kitchen and grill, patio seating was nice. But really it was about the outside time. Hardly anyone else used the beach areas so it felt like a private island beach. The pool was an average size and was overlooking the ocean where boats depart so that was also beautiful. Overall, family loved it, they definitely want to return soon."

Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
House
Islamorada, FL, USA

Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable offers accommodations in Islamorada, a 12-minute walk from Upper Matecumbe Key and 2.1 miles from Theater of the Sea on Islamorada. This vacation home provides air-conditioned accommodations with a balcony. The vacation home features parking on-site, an outdoor swimming pool, and a 24-hour front desk. With free Wifi, this 3-bedroom vacation home offers a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. The accommodation is non-smoking. A children's playground is also available at the vacation home, while guests can also relax in the garden. Windley Key is 2.7 miles from Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable, while Pigeon Key is 13 miles from the property. Miami International Airport is 74 miles away.

Amenities:

Internet • Pool • Security/Safety • Air Conditioner • Child Friendly • Breakfast • Other • View • Sports/Activities • Guest Services • Parking • Wellness Facilities

La Jolla Resort
Hotel
82216 Overseas Highway, Islamorada, FL, 33036, USA

Beachfront hotel in Islamorada with an outdoor pool
This smoke-free hotel features a private beach, an outdoor pool, and concierge services. WiFi in public areas is free. Additionally, tour/ticket assistance, a garden, and barbecue grills are onsite.
La Jolla Resort offers 20 air-conditioned accommodations with coffee/tea makers and irons/ironing boards. Flat-screen televisions come with cable channels.

Bathrooms include showers. Guests can surf the web using the complimentary wireless Internet access. Housekeeping is provided daily.


Recreational amenities at the hotel include a private beach and an outdoor pool.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "Good!!! " - "Ok" - "Very nice and easy to deal with" - "Beautiful beach with ewsy acdess to the beach " - "We love this property. This is the 4th time we have stayed and it never disappoints. " - "Location is great. Walking distance to brewery, Mangrove Mikes and Lorelei. Everyone is friendly. Cat on site. No place to put your toiletries. No tvs in bedrooms. Plenty of towels. Low water pressure. " - "Loved the La Jolla! Cannot wait to come back! "

Beach Residence Private overwater dock Heated Pool Mahi Key
House
Islamorada, FL, USA

Beach Residence Private overwater dock Heated Pool Mahi Key offers accommodations in Islamorada, 5.7 miles from Upper Matecumbe Key and 8.3 miles from Theater of the Sea on Islamorada. The air-conditioned accommodation is 1.4 miles from Sea Oats Beach. Florida Keys Aquarium Encounters is 24 miles away and John Pennekamp State Park is 27 miles from the vacation home. Offering a balcony with sea views, this vacation home also features a cable TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 3 bathrooms with a bath and a hair dryer. The accommodation is non-smoking. Guests can enjoy the outdoor swimming pool at the vacation home. Windley Key is 8.8 miles from Beach Residence Private overwater dock Heated Pool Mahi Key, while Pigeon Key is 19 miles from the property. Key West International Airport is 73 miles away.

Amenities:

Accessibility • Pet Friendly • Air Conditioner • Security/Safety • Guest Services • Barbecue/Outdoor Cooking • Pool • Parking • View • Internet • Other • Sports/Activities

Breezy Palms Resort
Apartment
80015 Overseas Highway, Islamorada, FL, 33036, USA

Beachfront, with outdoor pool
At Breezy Palms Resort, hit the beach, relax by an outdoor pool, or spend the day at a marina.
Each apartment features a kitchen with a refrigerator and a microwave, plus free WiFi and a TV with cable channels. Other amenities that guests will find include a sitting area and a coffee/tea maker. Weekly housekeeping is available.
Breezy Palms Resort offers 40 accommodations with coffee/tea makers. Accommodations offer separate sitting areas. Kitchens offer full-sized refrigerators/freezers, microwaves, and cookware/dishes/utensils. Bathrooms include bathtubs or showers.

Guests can surf the web using the complimentary wireless Internet access (speed: 50+ Mbps). Cable television is provided. Housekeeping is offered weekly and hair dryers can be requested. Housekeeping is provided on a limited basis.


Recreational amenities at the aparthotel include an outdoor pool.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "By far the best hotel I have stayed so far. Our room was right in front of the ocean and the view was amazing. The amenities inside the rooms were also top notch." - "Very nice property and friendly staff" - "Adorable updated unit. Friendly welcoming staff. " - "A little dated but very clean and nice atmosphere " - "The kind staff and clean pool. Excellent housekeeping as well the kitchen. We weree able to enjoy our time and make meals as needed. "

Breezy Palms Resort
Hotel
80015 Overseas Highway, Islamorada, FL, FL 33036, USA

Facing the beachfront, Breezy Palms Resort offers 3-star accommodations in Islamorada and has an outdoor swimming pool, private beach area and terrace. The property is located 2 miles from Upper Matecumbe Key, 4.5 miles from Theater of the Sea on Islamorada and 5.1 miles from Windley Key. Free WiFi is available and private parking can be arranged at an extra charge. Complete with a private bathroom equipped with a shower and free toiletries, the rooms at the hotel have a flat-screen TV and air conditioning, and certain rooms come with a balcony. Guest rooms will provide guests with a fridge. Speaking both English and Spanish, staff at the reception can help you plan your stay. Pigeon Key is 15 miles from Breezy Palms Resort, while John Pennekamp State Park is 23 miles from the property. Miami International Airport is 76 miles away.

Guest Reviews:

- "Heaven on the beach!" - "We enjoyed our night there. Very quiet, nice lounge chairs, outside bathroom was great. Most don’t have that. I’d stay t" - "I am coming back I found a new vacation spot!!" - "Great find!" - "Wonderful" - "Had a really nice time!" - "Only stayed one night but a great base for exploring the Keys" - "Good place for a stopover." - "Fab establishment on the water!" - "Exactly what you pay for. Very clean"

Sands of Islamorada
Hotel
80051 Overseas Highway, Islamorada, FL, 33036, USA

Suburban hotel in Islamorada with free parking
An outdoor pool, laundry facilities, and a garden are available at this hotel. Free WiFi in public areas and free self parking are also provided. Additionally, barbecue grills, a picnic area, and a front-desk safe are onsite.
Sands of Islamorada offers 9 air-conditioned accommodations with safes and coffee/tea makers. Each accommodation is individually furnished and decorated. Guests can make use of the in-room refrigerators and microwaves. Bathrooms include shower/tub combinations, bathrobes, complimentary toiletries, and hair dryers.

Guests can surf the web using the complimentary wireless Internet access. 20-inch flat-screen televisions come with premium cable channels. Additionally, rooms include irons/ironing boards and ceiling fans. Housekeeping is provided daily.


Recreational amenities at the hotel include an outdoor pool.

Guest Reviews:

- "great property. yes older, but well and recently remodeled. close to many essentials. definitely would come here again." - "Just perfect" - "Awesome view, nice room." - "Check in was a little confusing as no one at check-in and had to call a number on the front door. Not real inviting that is for sure. Place was clean and bed was comfortable. " - "Beautiful views of the water. Conveniently located close to shops and restaurants. Very clean. Beds were ok, hard to get a hold of staff but very friendly when we did. "

Hadley Resort and Marina
Hotel
82749 Overseas Highway,, Islamorada, FL, FL 33036, USA

This hotel is located in Islamorada, Florida. Hadley Resort and Marina features an outdoor swiming pool and free WiFi throughout the property. Each room at the Hadley Resort and Marina features a private bathroom, a kitchenette with a refrigerator and a microwave. Some rooms also have sea views or pool views. Other facilities offered at the property include dock space and a marina. A dock and a marina are offered at the property. The Theater of the Sea is located 1.8 mi from the hotel, the Tiki Bar at Holiday Isle is 1.5 mi away, and Founders Park Watersports is 4.8 mi from the property.

Guest Reviews:

- "Would definitely stay again." - "Loved it. Room next door was rather noisy after folks moved in." - "Nice hotel, but should be for the money charged." - "Great location to explore the keys" - "We had a Wonderful time with amazing views!" - "Nice room and lovely staff" - "Great value for the money; safe, clean. Will visit again!" - "Pls fix the bed"

Ragged Edge Resort & Marina
House
243 Treasure Harbor Dr, Islamorada, FL, 33036, USA

While you're here, you can enjoy all the comforts of home and more, including free WiFi and a TV, as well as a dock and climate control. Other amenities include laundry facilities, towels, a picnic area, and a ceiling fan.

Guest Reviews:

- "A great place to stay" - "Property was very clean and updated. The beds were comfortable and the showers were hot. The beach area looked nice and I liked the free bikes. We were only there for the night but we would gladly go back and spend more time. " - "great places " - "Nice relaxing Keysie vib. Comfy beds, friendly service, beautiful locatIon. The only negative might be the tiny shower and trying to adjust the water temperature. Otherwise, highly recommend!"

Sunset Inn
Hotel
82200 Overseas Highway, Islamorada, FL, FL 33036

Located in Islamorada, a 9-minute walk from Upper Matecumbe Key, Sunset Inn provides accommodations with a garden, free private parking and barbecue facilities. Featuring an outdoor swimming pool, the 3-star hotel has air-conditioned rooms with free WiFi, each with a private bathroom. Pigeon Key is 13 miles away and John Pennekamp State Park is 21 miles from the hotel. Selected rooms contain a kitchenette with a fridge and a microwave. Guest rooms at the hotel are equipped with a flat-screen TV with cable channels and a safety deposit box. Theater of the Sea on Islamorada is 2.2 miles from Sunset Inn, while Windley Key is 2.8 miles away. Miami International Airport is 75 miles from the property.

Guest Reviews:

- "Total blast. We fished, took in a eco-tour, snorkeled, travelled to other keys, and much more." - "Will come back again !" - "I will be back next summer! Thank you!" - "would book it again" - "I will stay there again!" - "Good budget option for a night or 2." - "Not very pleasant."

Matecumbe Resort
Resort
76261 Overseas Hwy, Islamorada, FL, 33036, USA

Beachside resort with outdoor pool
Guests at this beach resort will appreciate convenient onsite amenities such as charcoal grills and a picnic area.
Housekeeping is available on request.
Matecumbe Resort offers 36 accommodations with hair dryers and blackout drapes/curtains. Rooms open to patios. Accommodations offer separate sitting areas. Kitchens offer full-sized refrigerators/freezers, stovetops, microwaves, and separate dining areas. Bathrooms include showers.

Guests can surf the web using the complimentary wireless Internet access (speed: 100+ Mbps (good for 1–2 people or up to 6 devices)). Televisions come with cable channels. Irons/ironing boards, change of towels, and change of bedsheets can be requested. Housekeeping is provided on request.


A private beach and complimentary bicycles are featured at the resort. Other recreational amenities include an outdoor pool.

The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "This hotel was the final stop on our Florida road trip, and it was exactly what my son and I needed—a place to unwind and relax. There were plenty of activities to enjoy, such as ping pong and kayaking, and the pool was well-maintained. We stayed in an apartment-style room in the building near the beach, and the sunrise views were spectacular. The only downside was the reception hours, which seemed to operate on "island time." While there are no nearby cafes or stores, the famous Robbie's of Islamorada is not too far away. If I visit the Florida Keys again, I wouldn't hesitate to stay here."

Fisher Inn Resort & Marina
Hotel
84951 Overseas Highway, Islamorada, FL, FL 33036, USA

Located right on the shores of Islamorada, the Fisher Inn Resort & Marina is 14 miles from Key Largo. Guests will enjoy convenient beach access and a boat ramp as well as an outdoor pool and outdoor games on the property. Free Wi-Fi is included in all rooms of this Islamorada hotel and guests can also enjoy cable TV in the rooms. Some units offer a kitchenette so guests can prepare their own meals during their stay. Laundry facilities is available on site at the Fisher Inn Resort & Marina. Guests will also be able to enjoy various activities such as fishing, windsurfing, kayaking, paddle boarding and snorkeling during their stay. This oceanfront hotel is less than 10 minutes’ walk from the Theater of the Sea. The Holiday Isle Marina is also less than 1 mile away.

Guest Reviews:

- "Great quite Hotel" - "This was a great place for my weekend stay." - "Loved it here" - "Had a great time. Grand daughter enjoyed the pool and all of the games" - "Will go back for sure!!" - "Comfortable, clean and convenient location with great ocean view." - "Good but the pet fee should be $25 per day instead of $50 considering housekeeping only made the beds, supplied fresh to" - "We love the fisher inn and will continue to stay there!"

The Ocean View Inn & Pub
Hotel
84500 Overseas Hwy, Islamorada, FL, 33036, USA

Hotel in Islamorada with bars and an outdoor pool
Along with an outdoor pool, this smoke-free hotel has a restaurant and 2 bars/lounges. Free WiFi in public areas and free self parking are also provided. Other amenities include ATM/banking services.
Change of towels is available on request.
The Ocean View Inn & Pub offers 7 air-conditioned accommodations with hair dryers and complimentary toiletries. Rooms open to patios. Televisions come with cable channels.

Bathrooms include showers. Guests can surf the web using the complimentary wireless Internet access (speed: 25+ Mbps). Housekeeping is offered daily and change of towels can be requested.


Recreational amenities at the hotel include an outdoor pool.

Guest Reviews:

- "Very fun place to stay. Everything you need in one spot! " - "Awesome place to stay, restaurant and bar attached, outside bar and dining area overlooking the bay. Pool also very nice. " - "The highlight was the fun outside bar and restaurant, we had a blast!" - "The sheets were not clean But the spot of the pool is super"

Chesapeake Beach Resort
Resort
83409 Overseas Highway, Islamorada, FL, FL 33036, USA

Guests at this Islamorada oceanfront resort can enjoy free WiFi access. Windley Key Fossil Reef Geological State Park is 2 miles away. A 37-inch flat-screen cable TV and a small refrigerator are offered in each room at this Florida Chesapeake Beach Resort. Select rooms and suites have a balcony. Chesapeake Beach Resort features an outdoor pool with an ocean view. Guests can check out the History of Diving Museum (3 minutes’ walk) or see a show at the Theater of the Sea (4 minutes’ drive).

Guest Reviews:

- "My husband and I took a vacation. The Chesapeake resort was so relaxing so beautiful so very clean in the hospitality wa" - "Love it" - "Bewutiful, tranquil, relaxing. Very clean and the staff was exceptional!" - "The staff was very helpful, pleasant and friendly."

OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
House
Islamorada, Florida, USA

***June 2022 - Installed a new AC with Germicidal UV light air purifier, which improves air quality by sterilizing mold, bacteria, allergens and viruses: and of course, our housekeeping staff complies with the latest cleaning and disinfecting CDC guidelines. ***

ANGLERS REEF is a quiet oceanfront community of Key West inspired homes, streets, and walking paths, that wind through a quaint village-style retreat. Located at Mile Marker 85 by Theater of the Sea, Windley Key Geographical Site, Snake Creek Marina & some of the best bars and restaurants in Islamorada.

GREAT LOCATION
The house is in a quiet section of the community, away from the highway and just 2 homes from the ocean. Our porches are shaded and face a tree-lined yard with a view of the ocean.

OCEANFRONT RESORT-STYLE SWIMMING POOL
The pool is both heated & chilled so that it is always a perfect 87 degrees.

TWO PRIVATE SANDY BEACHES
The South Beach has a shoreline & ocean access. A tandem kayak sits on the beach for your use, (additional kayak, paddleboards, jet ski & boat rentals are available close by and available for drop-off to your beach or dock).

The North Beach, a white sandy beach, is located just steps from the house.

DEEP WATER MARINA
Our boat slip, with direct ocean access, is available for rent and is also just steps away from the house. But whether or not you use our slip, the marina is part of the community and enjoyed by all guests.

OUR HOUSE
Built in 2007, this home, is bright and cheery with tile floors, high ceilings, and many large windows. It is newly decorated for the Keys and surrounded by lush tropical landscaping.
The main floor has an open plan with, tile floors, granite counters, stainless appliances, flat screen TV w/DVD players, cable with ALL PREMIUM CHANNELS, A DVR, Fast WiFi & a SONOS wireless speaker system.

There are 2 bedroom suites with flat screen TV’s and private baths located on the 2nd floor. Both baths have frameless glass showers and granite vanities. Rear bedroom has an ocean view and a private porch.

ISLAMORADA
Parks in Islamorada, Village of Islands: Just 2 miles north is Islamorada Founders Park at MM 87 Bayside, which offers activity or relaxation for the whole family. An Olympic-sized pool with diving area, a shallow water beach, water sports rentals, ball fields, fishing jetty, bocce, tennis and basketball courts, vita course with 18 exercise stations, multi-purpose path, skate park and dog park all are within the 40-acre park. Fees may apply. Village municipal parks also include the Islamorada Library Beach and Anne’s Beach. There is the Windley Key State Geological Site, a state park, at the site of a former coral rock quarry. In addition to shady walks through unique foliage, fossils of sea creatures can be seen throughout the park. A free guidebook is available at the visitors center for use during your stay in the park. Islamorada also offers an 18-mile bicycle path that extends the length of the Village.

Scuba/Snorkel!: Islamorada, long recognized as the 'Sport Fishing Capital of the World,' is now an icon among sport divers for a similar reason: a massive population of tropical marine life. High-profile coral heads and broad ledges shelter huge congregates of French grunt and goat fish, while regal queen angelfish casually graze amid the reef recesses. Friendly green moray eels swim freely along the spur-and-groove channels, and reclusive nurse sharks lurk beneath the overhangs. Islamorada offers a wide variety of shallow coral reefs, mini walls, shipwrecks, and even an underwater habitat for scientific research, the Aquarius. To learn more about Islamorada or any other manner of local lore, stop by the Chamber of Commerce at MM 82.5.

Guest Reviews:

- "The house was great and is in a location we’ve visited every year for the past 5 years. The house was clean, owners were extremely quick and thorough with communication and had a great overall experience with them and their home. We would definitely stay here again. The community is perfect for friends or family and very convenient if you have a boat." - "My husband and I thoroughly enjoyed our stay at the property. The owner was extremely prompt in answering all of my questions and was a pleasure to deal with. The house was amazing. The property was very quiet and extremely clean. It provided us everything that we needed for a lovely stay. Next time we will plan ahead and rent a boat and it will be even more amazing! We can't wait to return. We highly recommend this property."

Pines & Palms Resort
Resort
80401 Old Highway, Islamorada, FL, FL 33036

This Islamorada resort in the Florida Keys is located near Alligator Reef. It features an oceanfront freshwater pool, a Tiki Bar and a private beach area. Each accommodations includes a full kitchen. A living area with a cable TV is included in all units at Pines & Palms Resort. The traditionally styled units feature light colors and island decor. Most offer a private terrace with ocean views. Guests at Resort Palms & Pines have access to kayak and bike rentals, private boat docks and premium sport fishing areas. A covered cabana with a barbecue grill, fridge and sink is available for guest use. This resort is less than 1 mi from Miss Islamorada Fishing Charters. The entrance to John Pennekamp Coral Reef State Park is less than 30 minutes’ drive away.

Guest Reviews:

- "Amazing stay!" - "Rest and relaxation" - "Amazing stay" - "Wish we could've stayed longer. We hope to get a chance to return." - "Home away from home" - "Palms & Pines - our home away from home - so glad we chose this place!" - "Family weekend" - "Strategic position!" - "Exceptional stay" - "Great place to stay in the keys." - "Relaxing getaway, you feel like your on a Caribbean island without leaving the states."

OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
House
Islamorada, Florida, USA

"Windley Cottage" is a private home in the exclusive gated community of Angler's Reef in Islamorada. This welcoming, tastefully-decorated home is located at mile marker 85, away from the highway , and just steps from the pool and docks. The “Bahamian conch style" home provides irresistible charm and comfort tucked in among lush landscaping. ts central location is perfect for exploring all of the Florida Keys!
Whether you’re looking for a couples’ retreat or an exciting Keys experience with the family, this home is the answer! Flexible bed arrangements. Call 239-250-4135 for more information. I
We have amenities for all ages! Enjoy a swim in our temperature-controlled pool. Paddle out to the sandbar on our complimentary paddle boards or kayaks. Cycle to the many gift shops and restaurants. Scuba or snorkel the nearby coral reefs and shipwrecks, rich with underwater wonders. Dive near the popular Alligator Reef Lighthouse, which is visible and easily accessible from Angler's Reef. For a fee, dock your boat in our protected lagoon with direct, deep-channel access on the Atlantic. Nearby marinas offer boat/jet ski rentals, fishing/scuba/snorkeling charters, and party boats for fun on the water. Whether you fish from shore or our docks, flats-fish in the back bays, or deep-water fish for big game, Islamorada has it all! Swim with the dolphins and learn about the local marine life at Theater of the Sea (1/2 mile from our home). Dine at one of the fabulous nearby restaurants, many offering nightly entertainment.

Just 2 miles north is Islamorada Founders Park at MM 87 Bayside. The park offers a shallow water beach, ball fields, playground, fishing jetty, driving cage, 3paddle ball courts, bocce, tennis, a large playground, and basketball courts, an exercise course with 18 stations, and a multi-purpose path within the 40-acre park. Bring your rental agreement for free entry to the park.

Other municipal parks include the Islamorada Library Beach and Anne’s Beach. The Windley Key State Geological Site, a state park, is a former coral rock quarry, where fossils of sea creatures can be seen throughout the park.

After a busy day, enjoy a glass of wine on one of our two private beaches. Play a board game on the back porch. Dim the pendant lights and turn on the fireplace as you cuddle up to watch your favorite movie after a busy day.

Just pack a few clothes and your toothbrush and head down to the Florida Keys for the vacation of a lifetime in the comfort and luxury of Windley Cottage! See why people from all over the world get sand in their toes and return here again and again!

Contactless check-in and check-out is on Saturdays. Please contact us if you want a different day. Our calendar is updated in real-time and posted rates are accurate. When you find the perfect dates for your stay, simply click on "Book Now".

STR#-24-0163
FL DBPR #DWE5403337

NOTE: We also own a vacation rental property on Cape Cod, MA. Visit Vrbo listing 3757615 for photos and further information.

Guest Reviews:

- "Everything about the property is 5 Stars!! We enjoyed our week!! We chose this property because of the pictures, location and previous reviews! We would love to come again in the future. From the moment we walked in to sleeping it was very immaculate, cozy and we felt right at home. This is a beautiful home and will highly recommend to anyone wanting to stay here. Linda & Roger we’re always readily available and even checked in to make sure everything was to our expectation! Thank you for a wonderful week! Tina & Darin"

Drop Anchor Resort & Marina
Resort
84959 Overseas Highway, Islamorada, FL, FL 33036, USA

Located adjacent to Windley Key Fossil Reef Geological State Park, this Islamorada resort features an ocean-side outdoor swimming pool. Beach towels, Kayaks, Paddle-boards & WiFi are included at this oceanfront resort and marina. A microwave, refrigerator and coffee-making facilities come standard in each a room at Drop Anchor Resort & Marina Resort and Marina. A flat-screen TV is also included. Trailer parking and boat docking are possible at Drop Anchor Resort & Marina Resort. Barbecue facilities, outdoor dining areas and hammocks are available as well. Theater of the Sea is just 9 minutes’ walk from Drop Anchor Resort & Marina Resort and Marina. Guests will be 6.9 miles from Indian Key Historic Park.

Guest Reviews:

- "Will definitely stay here again!" - "Perfect getaway" - "I want to shut out the receptionist, he’s so nice and so humble. I believe he’s really passionate about his job. I was s" - "Very comfortable" - "Nice view but cannot swim in the private beach" - "Great value for the location and amenities. Would definitely stay here again" - "I enjoyed Drop Anchor enough to revisit but disappointed with the additional charge, when I feel we already paid a fair"

Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
House
Islamorada, Florida, USA

Come stay at the Tipsy Turtle in Angler's Reef! This magnificent home with ocean views from all 4 balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef, a quiet oceanfront community in the Florida Keys. Angler's Reef is a boutique complex of 52 homes inspired by Native Conch & British West Indies architecture. Quaint streets & walking paths wind through this village-styled retreat. Amenities include a community pool overlooking the Atlantic Ocean and 500ft of private beach. The home's boat slip is available for rent with a deep channel out to the Atlantic ($500/week). Or launch our kayaks and Paddleboards from the private beach (kayaks and paddle boards available for all guests to use). This home has 2 Master bedrooms located on the 2nd floor. The first bedroom has a King Sleepy's Curve Foam Mattress and the Second has another King Sleepy's Curve Foam Mattress. Each bedroom has a private bathroom and each having a private porch with an ocean view, and has 2 more porches downstairs with ocean views for morning coffee or cocktails. Upgraded Queen Sleeper Sofa downstairs sleeps 2 more . Homes decor includes stainless appliances, granite counters, Brazilian cherry hardwood floors, 3 flat screen TVs with cable including Cable & WiFi. Check-in/Check-out days are Saturday. Message me should you wish to check in/out on a different day. Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

Islamorada is synonymous with the best fishing - gulf, backcountry or ocean. There are plenty of guides, charters or boat rentals. You can also try for hogfish, snapper, mahi, tuna, bonefish, tarpon, snook, & more. Right at the Anglers Reef docks you can catch mangrove snapper, ladyfish, jack crevalle, moonfish, grunts, mullet & barracuda depending on season. We had one lucky vacationer catch a 70 pound Tuna right off the docks.

For those who don't like fishing there is still a ton to do which is one of the reasons we chose Anglers Reef. The development and the Islamorada area have a lot to do for people who are not into fishing. Just hanging at our home on one of the four porches is enough of a full day for some.

Enjoy our spacious decks with a book or cocktail and the views of the turquoise waters and ocean breeze. Or enjoy the large community pool (heated in winter and cooled in summer!). And if that's not enough you can take a stroll thru the community or relax on the private beaches or you can launch Kayaks and Paddle boards right off our beaches.

Restaurants: a short 5 minute walk are Hog Heaven, Smugglers Grill and the Island Grill. By car a few miles away are lots of oceanfront or bay front restaurants to eat at. All are amazing. See our recommendation book in the home.

Attractions: Swim with dolphins at Theater of the Sea 1/2 mile south. Founders Park is just a mile north with concerts and lots to do. The Islamorada Chamber of Commerce visitors center is also near the entrance to Founders Park for local info as well as affordable postcards, posters, T-shirts and books.

Grocery & Other Shopping: Publix just opened at MM83 on the Island and is just 2 miles south of the home. For quick items Trading Post is a little further south. There is also a Winn Dixie a few minutes north (around Mile Marker 91 in Tavernier. There is also a West Marine, Bass Pro Shops and other cool little stores around the town.

Parks in Islamorada, Village of Islands: Just 2 miles north is Islamorada Founders Park at MM 87 Bayside, which offers activity or relaxation for the whole family. An Olympic-sized pool with diving area, a shallow water beach, water sports rentals, ball fields, fishing jetty, bocce, tennis and basketball courts, vita course with 18 exercise stations, multi-purpose path, skate park and dog park all are within the 40-acre park. Fees may apply. Village municipal parks also include the Islamorada Library Beach and Anne’s Beach. There is the Windley Key State Geological Site, a state park, at the site of a former coral rock quarry. In addition to shady walks through unique foliage, fossils of sea creatures can be seen throughout the park. A free guidebook is available at the visitors center for use during your stay in the park. Islamorada also offers an 18-mile bicycle path that extends the length of the Village.

Scuba/Snorkel! : Islamorada, long recognized as the 'Sport Fishing Capital of the World,' is now an icon among sport divers for a similar reason: a massive population of tropical marine life. High profile coral heads and broad ledges shelter huge congregates of French grunt and goat fish, while regal queen angelfish casually graze amid the reef recesses. Friendly green moray eels swim freely along the spur-and-groove channels, and reclusive nurse sharks lurk beneath the overhangs. Islamorada offers a wide variety of shallow coral reefs, mini walls, shipwrecks, and even an underwater habitat for scientific research, the Aquarius. To learn more about Islamorada or any other manner of local lore, stop by the Chamber of Commerce at MM 82.5.

*The Eagle - This 287 ft ship was intentionally sunk in 110 ft of water as a dive attraction, cloaked in sponge & coral, populated by grunt, harpoon & jack. *Davis Reef - Reef revered for its incredible concentration of grunts & schoolmaster snapper, as well as several amiable resident green morays, long accustomed to benign interaction with the dive masters. *Alligator Reef - Now marked by a 136-ft-tall lighthouse, on this spot in 1822 the USS Alligator grounded & sank while protecting a convoy from pirates; remains of the wreck are the twin piles of ballast stones, but the coral reef - in just 25 ft of water - is vibrant and alive. *Conch Wall - Offering a precipitous sloping wall & captivating concentrations of barrel sponge & gorgonia punctuating seafloor. *Crocker Wall - A 450+-foot-long wall in 50 ft of water. The wall has a 30 ft decline and features grunts, yellow tail &grouper with spur-and-groove coral & block coral.

*Pickles Reef - Reef's minutia in 15-25 ft of water.

Guest Reviews:

- "We had a wonderful vacation. My only “complaint” is that check out is at 9:30 am. Unless your flight is early, you’re stuck with a lot of idol time. However, I appreciate the necessity to do this in order to thoroughly clean. The house was well stocked and Scott was super responsive and easy to communicate with. We’ll definitely stay here again if they’ll have us!" - "Very nice house in a great little community" - "My family and I have stayed in numerous properties all over the Keys and can honestly say Anglers Reef was the best location and amenities. We rented two different homes and had boat slips too! So nice to have the kayaks and paddleboards. Our host Scott was very responsive as well. Highly recommend!"

Islamorada Vacation-Rentals on the Map

Compare the Best Vacation-Rentals in Islamorada – Addresses, Prices, Stars, Rating, and Review Count

Property Name Address Price ($) Star Rating Review Count Book
Cheeca Lodge & Spa 81801 Overseas Highway Mile Marker 82, Islamorada, FL, FL 33036, USA 865 5.0 8.7 977 Click here
Cheeca Lodge & Spa 81801 Overseas Highway, Mile Marker 82, Islamorada, FL, 33036, USA 298 5.0 9.2 1271 Click here
Casa Morada 136 Madeira Road, Islamorada, FL, FL 33036, USA 603 5.0 9.1 90 Click here
Amara Cay Resort 80001 Overseas Hwy, Islamorada, FL, 33036, USA 230 4.0 8.8 1256 Click here
Islander Resort 82100 Overseas Highway, Islamorada, FL, FL 33036, USA 348 4.0 8.7 1451 Click here
Islander Resort 82100 Overseas Highway, Islamorada, FL, 33036, USA 355 4.0 9.2 1006 Click here
Amara Cay Resort 80001 Overseas Highway, Islamorada, FL, FL 33036, USA 254 4.0 8.1 607 Click here
La Siesta Resort & Villas 80241 Overseas Highway, Islamorada, FL, 33036, USA 294 4.0 8.8 1001 Click here
La Siesta Resort & Villas 80241 Overseas Highway, Islamorada, FL, FL 33036, USA 240 4.0 8.3 339 Click here
The Islands of Islamorada 82779 Old Hwy, Islamorada, FL, 33036, USA 732 4.0 9.8 68 Click here
Bayside Villas by Islander Resort 81450 Overseas Highway, Islamorada, FL, FL 33036, USA 345 4.0 8.6 232 Click here
Pineapple Beach by Florida Keys Luxury Rentals 130 Aregood Lane, Islamorada, FL, 33036 2950 4.0 1 Click here
Anglers Reef Paradise 110 Anglers Way 110, Islamorada, FL, FL 33036, USA 400 4.0 9.6 19 Click here
Chesapeake Beach Resort 83409 Overseas Hwy, Islamorada, FL, 33036, USA 207 3.0 9.2 1577 Click here
The Islands of Islamorada 82779 Old Highway, Islamorada, FL, FL 33036, USA 795 4.0 9.3 17 Click here
Hadley Resort and Marina 82749 Overseas Hwy, Islamorada, FL, 33036, USA 160 3.0 7.8 1005 Click here
Islamorada Paradise Overlooking the Fabulous Florida Bay. 88540 Overseas Highway, Tavernier, FL, FL 33070, USA 189 4.0 9.8 6 Click here
Fisher Inn Resort & Marina 84951 Overseas Hwy, Islamorada, FL, 33036, USA 162 3.0 8.2 1004 Click here
Key Lime Cottage in the heart of Islamorada 76777 Overseas Highway, Islamorada, FL, FL 33036 308 4.0 9.3 3 Click here
Sunset Inn 82200 Overseas Hwy, Islamorada, FL, 33036-3637, USA 156 3.0 9.4 1002 Click here
EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS 87200 Overseas Highway, Islamorada, FL, FL 33036, USA 180 4.0 8.5 2 Click here
Drop Anchor 84959 Overseas Highway, 222, Islamorada, FL, 33036, USA 173 3.0 8.8 1001 Click here
Anglers Reef Vacation Rental 109 Anglers Way, Islamorada, FL, FL 33036, USA 495 4.0 9.5 2 Click here
Pelican Cove Resort & Marina 84457 Overseas Highway, Islamorada, FL, 33036, USA 188 3.0 8.2 1000 Click here
Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water views! Islamorada, FL, USA 966 4.0 10.0 2 Click here
Pines & Palms Resort 80401 Old Hwy, Islamorada, FL, 33036, USA 261 3.0 9.2 1000 Click here
Ocean View Penthouse Retreat amenities: tennis court heated Pool Vista Key Two Islamorada, FL, USA 582 4.0 1 Click here
Casa Morada 136 Madeira Road, Islamorada, FL, 33036, USA 520 3.0 9.4 410 Click here
Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada, FL, USA 617 4.0 1 Click here
Bayside Villas by Islander Resort 81450 Overseas Highway, Islamorada, FL, 33036, USA 331 3.0 8.8 397 Click here
Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada, FL, USA 627 4.0 1 Click here
The Caribbean Resort 117 Carroll St, Islamorada, FL, 33036, USA 639 3.0 10.0 154 Click here
Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada, FL, USA 737 4.0 1 Click here
Coconut Cove Resort and Marina 84801 Overseas Highway, Islamorada, FL, 33036, USA 190 3.0 9.0 140 Click here
Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada, FL, USA 802 4.0 1 Click here
Treasure Harbor 200 Treasure Harbor Dr, Islamorada, FL, 33036, USA 365 3.0 9.0 111 Click here
Hidden Gem Duplex in Heart of Islamorada Sleeps 8 82236 Overseas Highway, Islamorada, FL, 33036, USA 828 4.0 1 Click here
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort 84001 Overseas Hwy, Islamorada, FL, 33036, USA 313 3.0 9.0 109 Click here
Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada, FL, USA 841 4.0 1 Click here
Topsider Resort 75500 Overseas Hwy, Islamorada, FL, 33036, USA 446 3.0 8.8 62 Click here
Waterfront Wonder Islamorada, FL, USA 1007 4.0 1 Click here
Angler's Reef Resort by KeysCaribbean 84977 Overseas Highway, Islamorada, FL, 33036, USA 459 3.0 9.0 14 Click here
Isla Mirabelle - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada, FL, USA 1186 4.0 1 Click here
La Jolla Resort 82216 Overseas Highway, Islamorada, FL, 33036, USA 145 2.0 9.0 1003 Click here
Beach Residence Private overwater dock Heated Pool Mahi Key Islamorada, FL, USA 1282 4.0 1 Click here
Breezy Palms Resort 80015 Overseas Highway, Islamorada, FL, 33036, USA 136 2.0 8.8 567 Click here
Breezy Palms Resort 80015 Overseas Highway, Islamorada, FL, FL 33036, USA 166 3.0 8.3 1411 Click here
Sands of Islamorada 80051 Overseas Highway, Islamorada, FL, 33036, USA 195 2.0 8.8 389 Click here
Hadley Resort and Marina 82749 Overseas Highway,, Islamorada, FL, FL 33036, USA 202 3.0 7.1 1125 Click here
Ragged Edge Resort & Marina 243 Treasure Harbor Dr, Islamorada, FL, 33036, USA 179 2.0 9.4 203 Click here
Sunset Inn 82200 Overseas Highway, Islamorada, FL, FL 33036 164 3.0 8.5 1098 Click here
Matecumbe Resort 76261 Overseas Hwy, Islamorada, FL, 33036, USA 141 2.0 8.8 83 Click here
Fisher Inn Resort & Marina 84951 Overseas Highway, Islamorada, FL, FL 33036, USA 205 3.0 7.7 1006 Click here
The Ocean View Inn & Pub 84500 Overseas Hwy, Islamorada, FL, 33036, USA 199 2.0 9.6 7 Click here
Chesapeake Beach Resort 83409 Overseas Highway, Islamorada, FL, FL 33036, USA 536 3.0 8.0 846 Click here
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars Islamorada, Florida, USA 420 10.0 200 Click here
Pines & Palms Resort 80401 Old Highway, Islamorada, FL, FL 33036 282 3.0 9.0 762 Click here
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards Islamorada, Florida, USA 432 10.0 185 Click here
Drop Anchor Resort & Marina 84959 Overseas Highway, Islamorada, FL, FL 33036, USA 377 3.0 7.7 341 Click here
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach Islamorada, Florida, USA 436 10.0 180 Click here

Note: The prices for each Vacation-Rentals in Islamorada do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here) to get the latest prices.

Frequently Asked Questions

Vacation rentals in Islamorada that include a pool include:

  • Cheeca Lodge & Spa.- Review Count: 977, Rating: 8.7
  • Cheeca Lodge & Spa.- Review Count: 1271, Rating: 9.2
  • Casa Morada.- Review Count: 90, Rating: 9.1

Vacation rentals in Islamorada offering shuttle or transport options include:

  • Cheeca Lodge & Spa.- Review Count: 977, Rating: 8.7
  • Islander Resort.- Review Count: 1451, Rating: 8.7
  • Amara Cay Resort.- Review Count: 607, Rating: 8.1

These vacation rentals in Islamorada provide spa or wellness access:

  • Cheeca Lodge & Spa.- Review Count: 977, Rating: 8.7
  • Cheeca Lodge & Spa.- Review Count: 1271, Rating: 9.2
  • The Islands of Islamorada.- Review Count: 68, Rating: 9.8

Family-friendly vacation rentals in Islamorada include:

  • Cheeca Lodge & Spa.- Review Count: 977, Rating: 8.7
  • Cheeca Lodge & Spa.- Review Count: 1271, Rating: 9.2
  • Amara Cay Resort.- Review Count: 1256, Rating: 8.8

Pet-friendly vacation rentals in Islamorada include:

  • Casa Morada.- Review Count: 90, Rating: 9.1
  • Islander Resort.- Review Count: 1451, Rating: 8.7
  • Amara Cay Resort.- Review Count: 607, Rating: 8.1

Vacation rentals in Islamorada that include breakfast options include:

  • Cheeca Lodge & Spa.- Review Count: 977, Rating: 8.7
  • Cheeca Lodge & Spa.- Review Count: 1271, Rating: 9.2
  • Amara Cay Resort.- Review Count: 1256, Rating: 8.8

Vacation rentals in Islamorada with private or on-site parking include:

  • Cheeca Lodge & Spa.- Review Count: 977, Rating: 8.7
  • Cheeca Lodge & Spa.- Review Count: 1271, Rating: 9.2
  • Casa Morada.- Review Count: 90, Rating: 9.1

Some of the best Vacation Rentals in Islamorada are:

  • Cheeca Lodge & Spa.- Review Count: 1271, Rating: 9.2
  • Cheeca Lodge & Spa.- Review Count: 977, Rating: 8.7
  • Casa Morada.- Review Count: 90, Rating: 9.1

Some of the popular Vacation Rentals in Islamorada are:

  • Chesapeake Beach Resort.- Review Count: 1577, Rating: 9.2
  • Islander Resort.- Review Count: 1451, Rating: 8.7
  • Breezy Palms Resort.- Review Count: 1411, Rating: 8.3