Upper Matecumbe Key, FL

Travel Guide

Islamorada showing a beach bar
Islamorada showing a sandy beach
Islamorada
Islamorada featuring mangroves, general coastal views and a marina
Islamorada which includes a sandy beach, general coastal views and tropical scenes
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is ¥19,360 per night from Dec 7 to Dec 8
¥19,360
¥30,565 total
Dec 7 - Dec 8
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! (1,585 reviews)
Room was very clean, view was amazing, breakfast was great, and restaurants and activities nearby. Only issue was hot tub not working. Would’ve enjoyed that amenity!

Reviewed on Nov 24, 2025

Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is ¥32,430 per night from Dec 10 to Dec 11
¥32,430
¥47,025 total
Dec 10 - Dec 11
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 ...
9/10 Wonderful! (1,275 reviews)
This was a great property. Numerous dining options. I was so impressed with the grouper sandwich, possibly the best that I’ve eaten in 30 years in Florida and the Florida Keys. The customer service staff was amazing and so thorough informing guest at check-in of all of the amenities available to ...

Reviewed on Nov 23, 2025

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is ¥21,966 per night from Nov 30 to Dec 1
¥21,966
¥35,077 total
Nov 30 - Dec 1
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! (1,266 reviews)
Loved the resort

Reviewed on Nov 21, 2025

Amara Cay Resort
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

Breezy Palms Resort

2.5 out of 5
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

Breezy Palms Resort
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
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

The Islands of Islamorada
Treasure Harbor

Treasure Harbor

3 out of 5
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! (112 reviews)
Yes everything was clean and neat , staff very helpful and friendly

Reviewed on Nov 16, 2025

Treasure Harbor
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

Cities near Upper Matecumbe Key