Upper Matecumbe Key

Travel Guide

Islamorada featuring a beach bar
Islamorada showing a beach
Islamorada
Islamorada showing general coastal views, mangroves and a marina
Islamorada showing a sandy beach, general coastal views and tropical scenes
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
The price is HK$1,080 per night from 30 Oct to 31 Oct
HK$1,080
HK$1,740 total
30 Oct - 31 Oct
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! (1,241 reviews)
Awesome place!

Reviewed on 22 Oct 2025

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is HK$1,023 per night from 30 Oct to 31 Oct
HK$1,023
HK$1,667 total
30 Oct - 31 Oct
includes taxes & fees
Stay at this 4-star beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,264 reviews)
This was our second stay there and will definitely go back. The location is great and there is plenty of well-maintained beach area to enjoy. The room was large, clean and updated. However, the view from the room left a lot to be desired. We booked a standard room so we didn't have expectations one ...

Reviewed on 14 Oct 2025

Amara Cay Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
The price is HK$943 per night from 28 Oct to 29 Oct
HK$943
HK$1,498 total
28 Oct - 29 Oct
includes taxes & fees
Stay at this 3.5-star 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! (1,554 reviews)
Gem!
What a CLEAN and beautiful place! Vanessa at the front desk was awesome! Only stayed one night on the way to Key West, but I would definitely stay again!! So many amenities and your own private beach. 10/10

Reviewed on 20 Oct 2025

Chesapeake Beach 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! (550 reviews)
I had a lovely day for two nights. The beach was spectacular and the hotel was very clean and the staff were wonderful. Highly recommend.

Reviewed on 21 Oct 2025

Breezy Palms Resort
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy, Islamorada, FL
Stay at this 4-star 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! (67 reviews)
Great for family vacation with kids. love it

Reviewed on 20 Oct 2025

The Islands of Islamorada
5 bedroom - Deep Dockage & Heated Pool in Islamorada.

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

Islamorada
Stay at this vacation home in Islamorada. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Keys History & Discovery Center and Islamorada ...
10/10 Exceptional! (115 reviews)
This property is great and location couldn’t be better. Very close to a lot of restaurants, breweries and easy in and out with the boat. 5bdrms 4 bath was perfect for us. Got to meet an adult manatee and a juvenile manatee as well. Owners are awesome, got to meet them as well and communication prior ...

Reviewed on 24 Aug 2025

5 bedroom - Deep Dockage & Heated Pool in Islamorada.
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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