Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NT$5,933 per night from Jan 28 to Jan 29
NT$5,933
NT$8,439 total
Jan 28 - 2026/1/29
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (1,609 reviews)
Entire resort was clean and beautiful. Quiet location with beautiful rooms. We will return.
Reviewed on 2025/12/31
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
The price is NT$7,393 per night from Jan 4 to Jan 5
NT$7,393
NT$10,612 total
Jan 4 - 2026/1/5
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.8/10 Excellent! (1,271 reviews)
Was very nice , Did order cookies and brownies for the room Christmas night and that never happened! Fishing pole rental was ridiculous Food was great and good Keylime dessert !
Reviewed on 2025/12/28
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is NT$9,383 per night from Jan 4 to Jan 5
NT$9,383
NT$12,851 total
Jan 4 - 2026/1/5
includes taxes & fees
Book a stay at this 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! (1,278 reviews)
Good property but a little dated and understaffed. They are trying and they are hospitable but not a 5 star experience. Still one of the nicer resorts in the area.
Reviewed on 2025/12/29
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
Book a stay at this beach aparthotel in Islamorada. Enjoy free WiFi, a beach locale, and a marina. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (596 reviews)
Property was nice and easy to navigate, ocean view room was extra nice to have!
Reviewed on 2025/12/27
The Islands of Islamorada
82779 Old Hwy Islamorada FL
Book a stay at this beach villa in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada ...
9.6/10 Exceptional! (70 reviews)
Beautiful accommodations and location, very clean, many activities available at resort
Reviewed on 2025/11/25
Treasure Harbor
200 Treasure Harbor Dr Islamorada FL
Stay at this hotel in Islamorada. Enjoy free WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.8/10 Excellent! (119 reviews)
Great spot! Will be back someday hopefully.
Reviewed on 2025/12/29
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.
Check Upper Matecumbe Key hotel availability
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
4.5/5(51 reviews)
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
4/5(66 reviews)
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
4.5/5(141 reviews)
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 exploring the galleries in Keys History & Discovery Center during your trip to Islamorada.
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- Eco Pond
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