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 CA $206 per night from Sep 2 to Sep 3
CA $206
CA $334 total
Sep 2 - Sep 3
includes taxes & fees
Book a 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 ...
Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is CA $157 per night from Sep 29 to Sep 30
CA $157
CA $254 total
Sep 29 - Sep 30
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is CA $197 per night from Sep 15 to Sep 16
CA $197
CA $323 total
Sep 15 - Sep 16
includes taxes & fees
Book a 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 ...
Amara Cay Resort
See all 2,769 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
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 ...
8.8/10 Excellent! (737 reviews)
"Espectacular y muy limpio"

Reviewed on Sep 1, 2026

Breezy Palms Resort
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

Islamorada FL
Stay at this vacation home in Islamorada. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Lorelei Restaurant & Cabana Bar and Keys ...
10/10 Exceptional! (67 reviews)
"Absolutely amazing rental! The location is incredible, we loved being able to walk to so many shops and restaurants! Publix is right around the corner! The pool gets just the right amount of shade and sun! We have already rebooked!!"

Reviewed on Aug 4, 2026

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
Oceanfront Private Cottage!

Oceanfront Private Cottage!

Islamorada FL
Stay at this cottage in Islamorada. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions History of Diving Museum and Islamorada Brewery ...
10/10 Exceptional! (119 reviews)
"Beautiful home!! Had everything we needed for our 7 night stay. We will definitely be back."

Reviewed on Aug 23, 2026

Oceanfront Private Cottage!
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 family-friendly area.
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Cities near Upper Matecumbe Key

A beach with palm trees and white lounge chairs under a clear blue sky.

Islamorada

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