Top-Rated Hotels in Islamorada

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"

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."

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!"

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."

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 ."

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 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!"

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.

- "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"

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!"

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.

- "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"

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.

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

- "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......"

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.

- "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."

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.

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

- "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."

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.

- "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!"

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.

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

- "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."

The Ocean View Inn has an outdoor swimming pool, terrace, a restaurant and bar in Islamorada. The property is around 2.9 miles from Upper Matecumbe Key, 10 miles from Pigeon Key and 18 miles from John Pennekamp State Park. Dolphin Cove is 18 miles away and History of Diving Museum is 1.6 miles from the hotel. At the hotel, rooms include a closet. Complete with a private bathroom equipped with a shower and free toiletries, the rooms at The Ocean View Inn have a flat-screen TV and air conditioning, and certain rooms have a patio. Guest rooms will provide guests with a fridge. Popular points of interest near the accommodation include Theater of the Sea on Islamorada, Windley Key and Windley Key Fossil Reef Geological State Park. Miami International Airport is 72 miles from the property.

- "Excellent experience. Thank you." - "See you soon!" - "Quaint place to stay with beautiful environment and friendly hosts"

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.

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

- "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. "

Offering an outdoor pool and sun terrace, Caloosa Cove Resort is located in Islamorada in the Florida Region, 6 mi from Upper Matecumbe Key. Theater of the Sea on Islamorada is 11 mi from the property. All units feature a flat-screen TV, a balcony, and fully equipped kitchen. Some units have 2 flat-screen TVs and 2 balconies with an ocean view. Unites also have 1 or 2 full bathrooms. Towels are exchangeable daily. Even though this is a beachfront resort not every room has a water view. Guests can enjoy a meal at the on-site restaurant. The property has a private beach area. The area is popular for fishing. Windley Key is 11 mi from Caloosa Cove Resort, while Windley Key Fossil Reef Geological State Park is 11 mi away.

- "We’d stay again." - "It was a perfect spot! Beautiful, quiet, easy." - "Perfect, quiet getaway" - "So relaxing and fun! Staff super nice." - "Great place to stay would stay again." - "Beautiful, relaxing location." - "Next to the Sea Base for Scouts!" - "Great resort and I am already planning on next year to stay there" - "We had a wonderful stay and would definitely come back." - "A peaceful retreat in a picturesque setting."

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.

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

- "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!!"