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 $202 per night from Aug 12 to Aug 13
CA $202
CA $330 total
Aug 12 - Aug 13
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 ...
9.2/10 Wonderful! (1,364 reviews)
"2 reservations I made 2 weeks in advance for the property, both weren’t booked and I got no offers to make good. I was on my honeymoon and told them I would like a bottle of champagne at my table, never got that either. Not worth the money. Staff, facilities not what it used to be."

Reviewed on Jul 29, 2026

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is CA $227 per night from Aug 19 to Aug 20
CA $227
CA $358 total
Aug 19 - Aug 20
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 ...
8.8/10 Excellent! (1,313 reviews)
"Genuinely think this would be a wonderful resort! Unfortunately we ran into a few issues with the uncleanliness of the corridors which needed a good hoover and also had children running up and down the corridors at all hours of both nights of our stay and banging on doors. I did phone reception about ..."

Reviewed on Jul 29, 2026

Amara Cay Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is CA $212 per night from Aug 10 to Aug 11
CA $212
CA $318 total
Aug 10 - Aug 11
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. ...
9.2/10 Wonderful! (1,771 reviews)
"Room was super clean. Staff was so nice and good breakfast"

Reviewed on Jul 28, 2026

Chesapeake Beach Resort
See all 2,776 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! (713 reviews)
"The stay was very nice. The room me and my husband stay in was very clean. Staff were very friendly."

Reviewed on Jul 28, 2026

Breezy Palms Resort
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
Book a stay at this 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! (78 reviews)
"Love this property! Our family had the most amazing time in the villas. The location is great and the property is really well kept with amazing staff. We enjoyed the pool, the kids game area, pickle ball and relaxing in the home. Highly recommend!!"

Reviewed on Jul 13, 2026

The Islands of Islamorada
5 bedroom - Deep Dockage & Heated Pool in Islamorada.

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

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! (129 reviews)
"Amazing property!!Beautiful clean home in a great location! Deep-water dockage, pool, tiki, bait freezer, close to the restaurants, sandbar, & fishing, plenty of kitchen space to cook and eat and let's not forget our visits from our Manatee friend. Definitely memories were made never to be forgotten. ..."

Reviewed on Jul 24, 2026

5 bedroom - Deep Dockage & Heated Pool in Islamorada.
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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