Best Short-Term Rentals in Islamorada

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.

- "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!"

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.

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

- "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. "

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.

- "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"

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.

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

- "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!"

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.

- "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!"

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.

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

- "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."

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.

- "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."

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.

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

- "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."

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.

- "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."

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.

- "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."

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.

- "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"

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.

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

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.

- "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"

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.

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.

- "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!"

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.

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

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.

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

- "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 ."

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.

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

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.

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

- "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 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.

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

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.

- "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!"