Upper Matecumbe Key
Travel Guide
Visit Upper Matecumbe Key
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is €228 per night from 18 Jan to 19 Jan
€228
18 Jan - 19 Jan 2026
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! (1,602 reviews)
Great little place on highway 1 in Islamorada. Renovated, clean great bathrooms, balconies, 2 heated pools and a jacuzzi, wonderful breakfast excellent and friendly staff and a welcome champagne drink 😃. Wait did i forget to mention amazing ocean views with ample beach chairs and umbrellas. They ...
Reviewed on 26 Dec 2025
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
The price is €287 per night from 4 Jan to 5 Jan
€287
4 Jan - 5 Jan 2026
includes taxes & fees
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 their reviews. ...
8.8/10 Excellent! (1,267 reviews)
Clean rooms! Great resort , fun activities , very nice and quiet area , made my anniversary with my girlfriend very special!
Reviewed on 21 Dec 2025
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is €348 per night from 4 Jan to 5 Jan
€348
4 Jan - 5 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! (1,276 reviews)
It was over the top amazing
Reviewed on 27 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! (597 reviews)
Kitchen was clean, bed was wonderful. Enjoyed screened In porch.
Reviewed on 28 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! (70 reviews)
Beautiful accommodations and location, very clean, many activities available at resort
Reviewed on 25 Nov 2025
New - Oceanfront Estate - Private Beach - Heated Pool - Stunning
Islamorada FL
Stay at this beach holiday home in Islamorada. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Bud n' Mary's Dive Center and Hurricane ...
Upon arrival, we were amazed at the beauty of the location of the home. Everything was in prestine condition. The pool and beach are minutes away from the back door. We experienced a plethora of restaurants on the island. The owners were wonderful to work with. We definitely will be returning.
Reviewed on 16 Oct 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.
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
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
3/5(2 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(3 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 studying the exhibits at Keys History & Discovery Center during your trip to Islamorada.
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