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 NT$4,397 per night from Nov 18 to Nov 19
NT$4,397
NT$6,694 total
Nov 18 - Nov 19
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! (1,564 reviews)
Nice place, good location, friendly staff, clean room, good food, beat views, easy access to pool and beach.

Reviewed on 2025/11/9

Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is NT$6,182 per night from Nov 20 to Nov 21
NT$6,182
NT$9,052 total
Nov 20 - Nov 21
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! (1,259 reviews)
Beautiful grounds, immaculate rooms, divine sushi and meals! The pier is nonstop entertainment for kids, especially if they fish. There are activities for everyone in your family. Highly recommend this resort!

Reviewed on 2025/11/13

Cheeca Lodge & Spa
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 NT$4,802 per night from Nov 30 to Dec 1
NT$4,802
NT$7,464 total
Nov 30 - Dec 1
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! (1,245 reviews)
The rooms were clean, staff was friendly and helpful, food was delicious, the property was beautiful and loved how there was connections to the other resorts through van transportation or the Rum runner boat! Would definitely stay again!

Reviewed on 2025/11/8

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! (560 reviews)
Everything was perfect, recently remodeled, the best hotel for the price I've stayed at so far

Reviewed on 2025/11/8

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! (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 2025/10/27

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 2025/11/1

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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