Upper Matecumbe Key, FL
Travel Guide
Visit Upper Matecumbe Key
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is ￥35,332 per night from Aug 9 to Aug 10
￥35,332
￥51,624 total
Aug 9 - Aug 10
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 ...
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
The price is ￥24,838 per night from Aug 16 to Aug 17
￥24,838
￥39,819 total
Aug 16 - Aug 17
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 ...
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
The price is ￥23,795 per night from Aug 16 to Aug 17
￥23,795
￥35,904 total
Aug 16 - Aug 17
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! (1,745 reviews)
"The property was beautiful and well maintained. The check in staff and staff at the bar were not polite or helpful at all. Very disappointing. The food selection at 3 oclock was limited to two things when it didn’t close for two hours."
Reviewed on Jul 18, 2026
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! (708 reviews)
"Too many Iguanas and trash on the lawn."
Reviewed on Jul 17, 2026
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! (78 reviews)
"Love this property! Our family had the most amazing time in the villas. The location is great and the property is really well kept with amazing staff. We enjoyed the pool, the kids game area, pickle ball and relaxing in the home. Highly recommend!!"
Reviewed on Jul 13, 2026
5 bedroom - Deep Dockage & Heated Pool in Islamorada.
Islamorada FL
Stay at this vacation home in Islamorada. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Lorelei Restaurant & Cabana Bar and Keys ...
10/10 Exceptional! (128 reviews)
"This home was wonderful and offered easy boat access to the Gulf, making it the perfect place for our stay. We really appreciated all of the owners’ personal recommendations for places to shop and eat. They made exploring the area even more enjoyable.We loved fishing from the dock, where we were ..."
Reviewed on Jun 27, 2026
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.
Stay near popular Upper Matecumbe Key attractions
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