Upper Matecumbe Key Travel Guide

Tourist Guide

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

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
The price is AU$290 per night from 29 Sept to 30 Sept
AU$290
per night
29 Sept - 30 Sept
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! (1,532 reviews)
"Excelent"

Reviewed on 21 Sept 2025

Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
The price is AU$248 per night from 8 Oct to 9 Oct
AU$248
per night
8 Oct - 9 Oct
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! (1,211 reviews)
"I love it"

Reviewed on 21 Sept 2025

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is AU$373 per night from 1 Oct to 2 Oct
AU$373
per night
1 Oct - 2 Oct
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! (1,253 reviews)
"Beautiful peaceful clean"

Reviewed on 21 Sept 2025

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! (540 reviews)
"Quaint"

Reviewed on 21 Sept 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! (66 reviews)
"Beautiful property!"

Reviewed on 4 Aug 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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