Upper Matecumbe Key
Travel Guide
Visit Upper Matecumbe Key
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is CA $305 per night from Aug 6 to Aug 7
CA $305
CA $446 total
Aug 6 - Aug 7
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 CA $243 per night from Aug 10 to Aug 11
CA $243
CA $376 total
Aug 10 - Aug 11
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 CA $205 per night from Aug 16 to Aug 17
CA $205
CA $310 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. ...
9.4/10 Exceptional! (1,743 reviews)
"Great pool and beach area"
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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- Visit Islamorada
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- Visit Marathon
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- Visit Long Key
- Visit Plantation Key
- Visit Layton
- Visit Homestead
- History of Diving Museum
- Visit Largo Sound Village
- Sombrero Beach
- Visit Kendale Lakes
- Visit South Miami
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