Upper Matecumbe Key, FL

Travel Guide

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

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is ₩279,198 per night from Dec 22 to Dec 23
₩279,198
₩397,169 total
Dec 22 - Dec 23
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! (1,598 reviews)
The entire resort was wonderful.

Reviewed on Dec 17, 2025

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is ₩347,908 per night from Jan 4 to Jan 5
₩347,908
₩489,430 total
Jan 4 - Jan 5, 2026
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! (1,265 reviews)
very nice staff, quiet and comfortable

Reviewed on Dec 10, 2025

Amara Cay Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is ₩440,846 per night from Dec 19 to Dec 20
₩440,846
₩603,775 total
Dec 19 - Dec 20
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! (1,266 reviews)
Everything was awsome

Reviewed on Dec 7, 2025

Cheeca Lodge & Spa
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! (586 reviews)
The room was fantastically clean and the view from the balcony / sunrise was beautiful. It was everything we need for our stay to make it very enjoyable. The wild life in the area was a great bonus. We Loved watching the pelicans and spent the afternoon sat beside a host of iguanas

Reviewed on Dec 15, 2025

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! (69 reviews)
Beautiful accommodations and location, very clean, many activities available at resort

Reviewed on Nov 25, 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 WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.8/10 Excellent! (117 reviews)
I am obsessed with tiny houses and this one floats! It was so relaxing to sit on the deck and enjoy the view. The bed was very comfy and the gentle motion of the water put me right to sleep. The staff are friendly and helpful. Islamorada is beautiful and fun to explore.

Reviewed on Nov 25, 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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