Upper Matecumbe Key

Travel 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 S$273 per night from 12 Oct to 13 Oct
S$273
12 Oct - 13 Oct
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 S$272 per night from 14 Oct to 15 Oct
S$272
14 Oct - 15 Oct
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! (1,799 reviews)
"Boo"

Reviewed on 7 Oct, 2026

Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is S$492 per night from 14 Oct to 15 Oct
S$492
14 Oct - 15 Oct
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the pool and the helpful staff in their reviews. ...
9.4/10 Exceptional! (1,134 reviews)
"We got the poolside cabana king and it was perfect! Resort was immaculate! Already want to go back!"

Reviewed on 6 Oct, 2026

Islander Resort
See all 2,714 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.
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! (762 reviews)
"All good thanks"

Reviewed on 6 Oct, 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! (177 reviews)
"Jennifer was amazing. We drove all night and checked in. She was so kind and helpful. Really loved treasure harbor. I will be posting videos on my social media soon. Great stay and absolutely beautiful islamorada ❤️ We hope to come again in the future. Thanks - Angel"

Reviewed on 4 Oct, 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! (182 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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A beach with palm trees and white lounge chairs under a clear blue sky.

Islamorada

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