Islamorada - the ideal getaway for relaxation, fishing and water sports!
The area around Windley Key is highly rated by travellers for relaxation, sunsets and restaurants.
relaxation, water sports and beaches are just a few reasons you’ll love the area around Windley Key Fossil Reef Geological State Park.
If tranquillity, kayaking and relaxation are for you, don’t miss out on the area around History of Diving Museum!
Travellers choose the area around Anne s Beach for relaxation, fishing and water sports.
Enjoy beaches, shopping and beach walks during your next trip to Hallandale Beach!
Positioned on 27 acres of lush gardens and 1000 feet of private Beach, Cheeca Lodge & Spa is a luxury resort in Islamorada, Florida.
“The grounds and location were fantastic. Facilities great and safe for young families and staff all very friendly. Thoroughly recommended.”
Average review score: 8.5
636 hotel reviews
A tranquil and relaxing retreat directly on the beach in the Florida Keys, this property offers spacious accommodations complete with full kitchens and easy access to attractions and activities.
“Wonderful place! Great pool and hot tub.”
Average review score: 8.5
1142 hotel reviews
Featuring a unique tropical atmosphere and situated on an island in the Florida Keys, this resort offers WiFi and parking to guests. A cable TV and a private bathroom are included in every guestroom.
“Excellent location, service, cleanliness in the room, the views as well. Even though we did not have a direct view of the beach being in building 2, still we had our little view of the bay which was perfect.”
Average review score: 8
833 hotel reviews
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 and hot tub. WiFi is included in the resort fee.
“Location, location, location.The views are spectacular, the property is awesome and conveniently located. Juan at the Raft Shack (kayak and paddleboard hut) was awesome. Staff was courteous, friendly and accommodating.”
Average review score: 8.3
499 hotel reviews
Guests at this Islamorada oceanfront resort can start every day with a hot breakfast and enjoy a private beach area and oceanfront hot-water spa.
“How could you not like this place? Especially coming from the cold Midwest.”
Average review score: 8
407 hotel reviews
This privately-owned boutique hotel contains 16 suites. Caribbean inspired decor can be found throughout the property. Casa Morada is 600 metres from Upper Matecumbe Key.
“The atmosphere. A very relaxing and quiet place”
Average review score: 9.1
136 hotel reviews
This beachfront hotel is located in Islamorada, Florida and features transfer services within a 6 km radius. WiFi is included in the resort fee.
“Didn't eat there...but the place and it's atmosphere is just wonderful”
Average review score: 8.6
591 hotel reviews
Located in Islamorada in the Florida Keys, this property is nestled on its own private beach and offers a cabana cafe and a saltwater lagoon. Theatre of the Sea is less than 1 mile away.
“Hotel property has own private beach. Great views. Staff accommodating. You also allowed to visit sister property next door.”
Average review score: 8.6
620 hotel reviews
Featuring free WiFi and an outdoor pool, La Jolla Resort offers accommodation in Islamorada, 800 metres from Upper Matecumbe Key. Free private parking is available on site.
“Beautiful views; plenty of bikes, kayaks and paddle boards; well kept and pretty grounds”
Average review score: 8.6
Average review score: 8.8
This Islamorada resort in the Florida Keys is located near Alligator Reef. It boasts an oceanfront freshwater pool, a Tiki Bar and a private beach area. Each accommodation includes a full kitchen.
“Everything was nice, close food, clean pool wonderful staff”
194 hotel reviews
Average review score: 8
This resort is situated on one-quarter mile of private beach on Long Key between Islamorada and Marathon. Bright spacious rooms, 2 swimming pools and snorkeling are available.
“Extra comfy beds. Great hotel.”
139 hotel reviews
Average review score: 7
Located in Islamorada, Florida, this beachfront inn offers an outdoor pool and a private beach area. A marina is on site as well.
“Love 💕 finding places like this. The most perfect little hotel in my opinion. The room was clean and comfy and I was lucky enough to have been offered an upgrade upon arrival. The place just screams laid-back charm and happiness as you pull in. The lovely lady on reception was a delight. The whole place has bags of character. I travel all over America from corner to corner and I've stayed in hundreds of hotels and motels on my road trips and this has got to be up there with the top 10. Not because it was the "poshest" or even the cleanest or biggest etc but because it has charm and a warm welcome. The beds are comfy the pool and the view are gorgeous and the amenities are all that I needed.... and ref: a previous comment about insects I never saw one! If u want sterile boring pristinness stay at the Ritz and pay those prices. All I saw were gorgeous birds little lizards and the cutest little cat. I will definitely come back here again and the great lady on reception ( manageress ) should be sent round other hotels to teach less friendly and accommodating receptionists how it's done 😊”
Average review score: 9.1
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.
“I'm a little hesitant to review as I love this Hidden Treasure....it was just the right amount of everything to make a Great relaxing Vacation.... The rooms, the pool, the sunsets.. The people... A slice of Paridise 🌴☀️”
289 hotel reviews
Average review score: 7.9
Offering free WiFi and a year-round outdoor pool, Matecumbe Resort is set in Islamorada, 9 km from Upper Matecumbe Key. Theater of the Sea on Islamorada is 13 km away.
Average review score: 9.1
Offering a private beach, this adults only Islamorada resort is 3.8 km from Windley Key Fossil Reef Geological State Park. Snorkelling equipment, paddles boards, and free Wi-Fi are provided.
“A small hotel, very comfy, very cozy and beautiful. The pool and solarium area is outstanding. The staff is super friendly and helpful and want to make sure you are as happy as possible. They lighted up the fireplace next to the sea for us to watch the stars! If you are going to Keys, do not miss it!!!”
Average review score: 8.4
This Islamorada, Florida inn boasts an outdoor pool with a hot tub and a boat dock with a ramp. Guests will be 4 miles from Theater of the Sea and 2 miles of Indian Key Historic State Park.
“Location perfect. Apartment very clean. Bed comfortable. Staff happy & friendly. Pool & beach well maintained.”
Located in Islamorada, these Florida Keys villas feature a full kitchen and free WiFi. The villa is 2 minutes’ walk from a private beach.
Average review score: 6.7
Featuring free WiFi throughout the property and free breakfast, Smugglers Cove Resort and Marina is a pet-friendly accommodation in Islamorada. Guests can enjoy the on-site restaurant.
“Staff friendly and 1/2 price food and drink special. Renee and Dixie are outstanding bartenders and people.”
334 hotel reviews
Average review score: 8.3
Offering free Wi-Fi and located in the Florida Keys, this motel is 6.2 km from Tavernaero Park Airport. All rooms feature a flat-screen cable TV. The property offers free parking.
“The locations, The owner, the staff It is familiar”
Average review score: 7.6
Offering a sandy beach with private lagoon, this Islamorada resort is 2.8 miles from Windley Key Fossil Reef Geological State park.
“Beautiful resort. Excellent views of sunset. Incredible patio.”
Offering a year-round outdoor pool and views of the sea, Little Basin Villas is located in Islamorada in the Florida Region. Free private parking is available on site.
Offering a year-round outdoor pool, Manatee Bay is located in Islamorada, 5 km from Windley Key. Theater of the Sea on Islamorada is 6 km away. Free WiFi is featured throughout the property.
Average review score: 6.2
These beachfront apartments, located in Islamorada, Florida, feature an outdoor pool. Days Inn and Suites Key Islamorada also offers free Wi-Fi and all rooms include a cable TV and refrigerator.
“I don't have time but was very good for my needs I will stop and stay there again”
Average review score: 8.4
Offering a public outdoor pool and sun terrace, Caloosa Cove Resort & Marina is situated in Islamorada in the Florida Region, 9.6 km from Upper Matecumbe Key.
“very relaxed setting with amazing pool and surroundings”
Set in Islamorada, 15 km from Upper Matecumbe Key, Angler's Reef Resort Villas features air-conditioned rooms with free WiFi. Free private parking is available on site. All rooms have a flat-screen...
Featuring an outdoor pool, 110 Anglers Way is a detached holiday home located in Islamorada. The air-conditioned unit is 300 metres from Windley Key. Free WiFi is provided .
131 Anglers Way is a holiday home with an outdoor pool, set in Islamorada, 300 metres from Windley Key. The holiday home is 900 metres from Theater of the Sea on Islamorada.
Located 300 metres from Windley Key in Islamorada, this holiday home features a garden with a year-round heated outdoor pool.
