Upper Matecumbe Key
Travel Guide
Visit Upper Matecumbe Key
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is RM771 per night from 22 Dec to 23 Dec
RM771
RM1,096 total
22 Dec - 23 Dec
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,597 reviews)
Idyllic beautiful beach setting, clean comfortable rooms, lovely setting.
Reviewed on 14 Dec 2025
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
The price is RM960 per night from 8 Jan to 9 Jan
RM960
RM1,351 total
8 Jan - 9 Jan 2026
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy a private beach, 3 bars/lounges and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
8.8/10 Excellent! (1,268 reviews)
I would give this hotel one the highest ratings for my most recent stays in the area. The views were spectacular. All of the staff were very friendly and helpful. Very very minor thing was the condition of the furniture and electrical sockets weren't the best quality but I just loved everything else ...
Reviewed on 16 Dec 2025
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is RM2,034 per night from 15 Jan to 16 Jan
RM2,034
RM2,586 total
15 Jan - 16 Jan 2026
includes taxes & fees
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (1,267 reviews)
Everything was awsome
Reviewed on 7 Dec 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Breezy Palms Resort
80015 Overseas Highway Islamorada FL
Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...
8.8/10 Excellent! (587 reviews)
Spotless room- right on beach- really enjoyed
Reviewed on 17 Dec 2025
The Islands of Islamorada
82779 Old Hwy Islamorada FL
Stay at this beach villa in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada Brewery ...
9.6/10 Exceptional! (69 reviews)
Beautiful accommodations and location, very clean, many activities available at resort
Reviewed on 25 Nov 2025
Treasure Harbor
200 Treasure Harbor Dr Islamorada FL
Stay at this hotel in Islamorada. Enjoy free Wi-Fi, free parking and premium bedding. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.8/10 Excellent! (117 reviews)
I am obsessed with tiny houses and this one floats! It was so relaxing to sit on the deck and enjoy the view. The bed was very comfy and the gentle motion of the water put me right to sleep. The staff are friendly and helpful. Islamorada is beautiful and fun to explore.
Reviewed on 25 Nov 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Florida Keys Brewing Co.
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.
History of Diving Museum
Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.
Hurricane Monument
The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway.
Bud n' Mary's Dive Center
Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this family-friendly area.
Islamorada Brewery & Distillery
You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.
Keys History & Discovery Center
You can spend time studying the exhibits at Keys History & Discovery Center during your trip to Islamorada.
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