Upper Matecumbe Key

Travel Guide

Upper Matecumbe Key
Upper Matecumbe Key
Upper Matecumbe Key
Upper Matecumbe Key
Upper Matecumbe Key
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is P18,106 per night from Apr 29 to Apr 30
P18,106
P24,798 total
Apr 29 - Apr 30
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 ...
9.2/10 Wonderful! (1,303 reviews)
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Reviewed on Mar 29, 2026

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is P14,900 per night from Apr 14 to Apr 15
P14,900
P20,168 total
Apr 14 - Apr 15
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! (1,677 reviews)
Everything was lovely! Staff checked in daily via text which i think is a nice touch, the beach and pool areas were readily available with chairs and towels and our villa was so cute with everything you could need in a little kitchen and bathroom. Breakfast was from 6a-10a and it was what you'd expect ...

Reviewed on Mar 29, 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is P15,900 per night from Apr 19 to Apr 20
P15,900
P22,317 total
Apr 19 - Apr 20
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! (1,263 reviews)
Property was truly beautiful with friendly staff and amazing amenities. The free shuttle to the other resorts was a great surprise as well. We took the Rum Runner for breakfast (shout out to Captain Dave and Bruce for being amazing). In my opinion, Amara Cay was the nicest of the three resorts if ...

Reviewed on Mar 28, 2026

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! (644 reviews)
Clean room, good staff and convenience location for a visit.

Reviewed on Mar 24, 2026

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 ...
9.8/10 Exceptional! (73 reviews)
Phenomenal hotel, Marcel and Jackie were amazing with the kids and the activities offered. This is the first hotel where I feel there is great value in the resort fee with all that's included.

Reviewed on Mar 9, 2026

The Islands of Islamorada
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr Islamorada FL
Stay at this houseboat in Islamorada. Enjoy free WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (147 reviews)
There is a really great Mexican place to walk to and a great bagel place that also serves breakfast and lunch. The boats have air conditioning, 2 large beds, bathroom and living area with a couch, small kitchen and table. It was very relaxing. We will definitely go back. Also has a beautiful pool ...

Reviewed on Mar 25, 2026

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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