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 3.876.682 ₫ per night from 21 Sept to 22 Sept
3.876.682 ₫
6.263.964 ₫ total
21 Sept - 22 Sept
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
The price is 3.930.019 ₫ per night from 22 Sept to 23 Sept
3.930.019 ₫
5.884.784 ₫ total
22 Sept - 23 Sept
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. ...
9.2/10 Wonderful! (1,778 reviews)
"Nice pool, great breakfast with seating outside with nice views"

Reviewed on 19 Sept 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is 4.021.733 ₫ per night from 22 Sept to 23 Sept
4.021.733 ₫
6.427.145 ₫ total
22 Sept - 23 Sept
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. ...
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 ...
9/10 Wonderful! (749 reviews)
"It was very cozy. I was able to relax while I was celebrating my anniversary with my wife. The bed was super comfortable. The shower was excellent, and the staff was very friendly."

Reviewed on 20 Sept 2026

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! (175 reviews)
"Amazing location and well equipped. Loved the local vibe, didn't see a manatee but plenty of green iguanas. Property was comfortable with great AC."

Reviewed on 9 Sept 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 ...
9.8/10 Exceptional! (183 reviews)
"Property was quiet and on the water. Room was big enough. Parking is a little tight."

Reviewed on 17 Sept 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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