Upper Matecumbe Key Travel Guide

Tourist Guide

A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.
A pier extending into calm waters with a covered seating area and a sandy beach.
A pelican standing on a wooden dock.
A pier with birds perched on poles, a sign, and a bridge in the background.
A calm lake with a reflection of trees and a cloudy sky.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is Rp3.279.536 per night from 19 Nov to 20 Nov
Rp3.279.536
Rp5.012.326 total
19 Nov - 20 Nov
includes taxes & fees
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 in their ...
Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundable
The price is Rp2.731.286 per night from 10 Nov to 11 Nov
Rp2.731.286
Rp4.089.809 total
10 Nov - 11 Nov
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
9.4/10 Exceptional! (1,808 reviews)
"Amazingly great.can't wait to go back!!"

Reviewed on 7 Nov 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is Rp3.039.133 per night from 16 Nov to 17 Nov
Rp3.039.133
Rp4.741.361 total
16 Nov - 17 Nov
includes taxes & fees
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 their reviews. ...
8.8/10 Excellent! (1,331 reviews)
"Have been staying here for years. The restaurant is excellent. Staff is nice. Unfortunately, the resort has become dog friendly. For this reason I will no longer stay here."

Reviewed on 7 Nov 2026

Amara Cay Resort
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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
Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...
Breezy Palms Resort
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr Islamorada FL
Stay at this houseboat in Islamorada. Enjoy free Wi-Fi, free parking and premium bedding. Our guests praise the helpful staff in their reviews. Popular attractions ...
9/10 Wonderful! (181 reviews)
"It was an amazing experience to stay on the houseboat. I love being on the water!"

Reviewed on 6 Nov 2026

Treasure Harbor
Island Bay Resort

Island Bay Resort

2.5 out of 5
92530 OVERSEAS HIGHWAY Tavernier FL
Stay at this beach aparthotel in Tavernier. Enjoy free Wi-Fi, free parking and a private beach. Our guests praise the helpful staff in their reviews. Popular ...
10/10 Exceptional! (190 reviews)
"This place is so nice and quaint. The cabanas were wonderful! It rained most of our trip but our trip was not ruined because of the cabanas and all of the hammocks and sitting areas here. The availability of using kayaks and paddle boards were a lot of fun. The host was wonderful! She gave so many ..."

Reviewed on 3 Nov 2026

Island Bay Resort
See all properties in Upper Matecumbe Key
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.

Stay near popular Upper Matecumbe Key attractions

A marina with boats docked, a motel, and a cafe.

Bud n' Mary's Dive Center

8.8/10 (504 reviews)
Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this relaxing area.
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