Upper Matecumbe Key

Travel Guide

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

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is S$262 per night from 24 Nov to 25 Nov
S$262
24 Nov - 25 Nov
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,582 reviews)
Beautiful resort with lots of included activities & water sports. Friendly staff. Clean rooms.

Reviewed on 17 Nov, 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 S$439 per night from 1 Dec to 2 Dec
S$439
1 Dec - 2 Dec
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! (1,270 reviews)
Everything about our stay was amazing and exceeded our expectations in every way!!

Reviewed on 17 Nov, 2025

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is S$294 per night from 1 Dec to 2 Dec
S$294
1 Dec - 2 Dec
includes taxes & fees
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 their reviews. ...
8.8/10 Excellent! (1,265 reviews)
This resort was beautiful, clean and fantastic. The staff was friendly and helpful. We had a wonderful day and will be back.

Reviewed on 20 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
Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...
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 19 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 beach villa in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada Brewery ...
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 hotel in Islamorada. Enjoy free Wi-Fi, free parking and premium bedding. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.8/10 Excellent! (111 reviews)
Yes everything was clean and neat , staff very helpful and friendly

Reviewed on 16 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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