Upper Matecumbe Key

Travel Guide

Upper Matecumbe Key
Upper Matecumbe Key
Upper Matecumbe Key
Upper Matecumbe Key
Upper Matecumbe Key
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundable
The price is P12,192 per night from May 21 to May 22
P12,192
P17,171 total
May 21 - May 22
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! (1,718 reviews)
Breakfast was one of the best in the world…

Reviewed on May 14, 2026

Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundable
The price is P14,676 per night from May 21 to May 22
P14,676
P21,001 total
May 21 - May 22
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! (1,310 reviews)
Exelente service but the room need more clean and attention

Reviewed on May 11, 2026

Cheeca Lodge & Spa
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is P12,527 per night from Jun 1 to Jun 2
P12,527
P18,238 total
Jun 1 - Jun 2
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,009 reviews)
I think some of the outdoor cushions could be updated.

Reviewed on May 13, 2026

Islander 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! (675 reviews)
We stayed for 3 days. Breezy Palm is small quite and on the beach. Very clean and cozy. They have Boat rentals available. Great place to lounge in the sun. Nice breeze coming off the water. Plenty of parking. Will stay again on future trips to the Keys.

Reviewed on May 13, 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 ...
9.6/10 Exceptional! (75 reviews)
The "suite" was a single room with a king and pullout sofa, there was no separation. So if you are traveling with children be aware that this is the same as a double queen at any other hotel room.

Reviewed on Apr 30, 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! (153 reviews)
This place is absolutely incredible. It offers a perfect harmony with nature—you immediately feel relaxed and at peace as soon as you arrive. The atmosphere is calm, quiet, and truly refreshing, making it the perfect escape from everyday stress. The fishing experience here is amazing. Whether you're ...

Reviewed on May 3, 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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