Upper Matecumbe Key

Travel Guide

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

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
The price is P11,732 per night from Nov 13 to Nov 14
P11,732
P17,178 total
Nov 13 - Nov 14
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! (1,256 reviews)
Well staffed and very prompt in requests. Our first visit there recommended by my children that have stayed often. Very efficient and polite and courteous in this ugly world it was a welcome feeling. We will be back

Reviewed on Nov 10, 2025

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
The price is P8,345 per night from Nov 16 to Nov 17
P8,345
P12,704 total
Nov 16 - Nov 17
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! (1,564 reviews)
breakfast was very good, but it was totally self service clean up as well. The beach in the keys is nothing special. The kayak was included for one hour if you want a fishing rod or two hours with two people only no fishing rod.

Reviewed on Nov 10, 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 P9,115 per night from Nov 30 to Dec 1
P9,115
P14,168 total
Nov 30 - Dec 1
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! (1,246 reviews)
Love

Reviewed on Nov 10, 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! (558 reviews)
Love this resort. Friendly check-in, room is always spotless and lovely outside area with beautiful views of the water. We have stayed here multiple times now - best spot in the keys!

Reviewed on Nov 6, 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 Oct 27, 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! (109 reviews)
The houseboat was so cute! The staff was very friendly and helpful. We really enjoyed out stay. The pool was new and clean. We would definitely come back.

Reviewed on Nov 1, 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.

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