Upper Matecumbe Key

Travel Guide

Islamorada which includes a beach bar
Islamorada which includes a sandy beach
Islamorada
Islamorada which includes a marina, mangroves and general coastal views
Islamorada featuring general coastal views, tropical scenes and a beach
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
The price is RM834 per night from 3 Nov to 4 Nov
RM834
RM1,221 total
3 Nov - 4 Nov
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 ...
9/10 Wonderful! (1,260 reviews)
A few problems with the room, ex. Coffee maker, sink in bathroom, shower, but over all excelent

Reviewed on 27 Oct 2025

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
The price is RM513 per night from 5 Nov to 6 Nov
RM513
RM813 total
5 Nov - 6 Nov
includes taxes & fees
Stay at this 3.5-star 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! (1,548 reviews)
I was very pleased with the resort. It’s a quiet hidden gem with a friendly and helpful staff. I would love to stay here again.

Reviewed on 27 Oct 2025

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is RM648 per night from 30 Nov to 1 Dec
RM648
RM1,007 total
30 Nov - 1 Dec
includes taxes & fees
Stay at this 4-star beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,271 reviews)
Hermoso lugar para descansar y estar en familia, una vibra única

Reviewed on 28 Oct 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 ...
8.6/10 Excellent! (551 reviews)
Peaceful stay
Absolutely loved my stay. However, the beds are not the most comfortable. That is my only complaint.

Reviewed on 27 Oct 2025

Breezy Palms Resort
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy, Islamorada, FL
Stay at this 4-star 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 27 Oct 2025

The Islands of Islamorada
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr, Islamorada, FL
Stay at this 3-star 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! (108 reviews)
Brand new houseboats, very clean & comfortable, new pool area which was great to relax & have a dip. Lots of wildlife in vicinity

Reviewed on 10 Oct 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