Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
$178 nightly
The price is $201 total per night from Dec 1 to Dec 2
$201 total
Dec 1 - Dec 2
Total with taxes and 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! (1,574 reviews)
Good spot.
Reviewed on Nov 15, 2025
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$298 nightly
The price is $336 total per night from Dec 1 to Dec 2
$336 total
Dec 1 - Dec 2
Total with taxes and 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 ...
9/10 Wonderful! (1,270 reviews)
Everything about our stay was amazing and exceeded our expectations in every way!!
Reviewed on Nov 17, 2025
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$205 nightly
The price is $231 total per night from Nov 30 to Dec 1
$231 total
Nov 30 - Dec 1
Total with taxes and 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! (1,266 reviews)
Loved the resort
Reviewed on Nov 21, 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
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! (572 reviews)
Beautiful oceanfront room, renovated, clean. Deducted a star because the blinds in the bedroom (parking lot side) were not sufficient to darken the room at night. Needs blackout curtains!
Reviewed on Nov 19, 2025
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! (68 reviews)
i like the fact that there's beach area but it was difficult to walk in an out of it due to the rocks. The pool filter could have been cleaned during our stay as there was multiple days of debris caught in the drain trap. would have enjoyed more dining options. Room was available before check in ...
Reviewed on Oct 27, 2025
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! (111 reviews)
Yes everything was clean and neat , staff very helpful and friendly
Reviewed on Nov 16, 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
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 relaxing area.
Islamorada Brewery & Distillery
You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.
MoradaWay Arts & Cultural District
You can spend time browsing the exhibits at MoradaWay Arts & Cultural District during your travels in Islamorada.
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- Bud n' Mary's Dive Center
- Florida Keys Brewing Co.
- History of Diving Museum
- Islamorada Brewery & Distillery
- MoradaWay Arts & Cultural District
- Matecumbe United Methodist Church
- Hurricane Monument
- Everglades National Park
- John Pennekamp Coral Reef State Park
- Baker's Cay Resort Beach
- Jimmy Johnson's Big Chill
- Fiesta Key
- Anne's Beach
- Founders Park
- Long Key State Park
- Harry Harris Park
- Islamorada County Park
- Florida Keys Dive Center
- Bluefin Rock Harbor Marina
- Pigeon Key
- Jacob's Aquatic Center
- Windley Key Fossil Reef Geological State Park
- Sunset Drive Beach
