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 RM831 per night from 20 Nov to 21 Nov
RM831
RM1,217 total
20 Nov - 21 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! (1,268 reviews)
Jess was great when checked in, made us feel right at home. The entire resort is beautiful, clean, well maintained. Although the rooms are spacious they’re starting to show their wear and tare, carpets needs a good cleaning or just install tile. Butch and Cole are great at the pool bar and as always ...

Reviewed on 3 Nov 2025

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
The price is RM591 per night from 10 Nov to 11 Nov
RM591
RM900 total
10 Nov - 11 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! (1,556 reviews)
Room was awesome and the amenities were great! Loved our stay!!!

Reviewed on 3 Nov 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 RM645 per night from 30 Nov to 1 Dec
RM645
RM1,003 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! (1,277 reviews)
Great stay except for the fact that we could not watch the World Series in the comfort of our room!! Really? Other than that thoughtless error our stay was relaxing and fun.

Reviewed on 3 Nov 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! (554 reviews)
The room was cute. I had reserved a king bed, but got 2 queen and they said that they couldn't do anything about that. The room phone didn’t work. The cable TV kept "rebooting" every 10 mins & would take 5 mins to reset. Some dishes were cracked & some burners on the stove didn't work. We made due ...

Reviewed on 4 Nov 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! (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 1 Nov 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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