Upper Matecumbe Key Cottages

A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.

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Recommended hotels in Upper Matecumbe Key

A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.

1. Chesapeake Beach Resort

Matecumbe

Phelicia

includes taxes & fees

3 Nov - 4 Nov

A patio with a wooden table and chairs, a sofa, and a striped ottoman. There are palm trees and a view of the beach.

2. Islander Resort

Matecumbe

includes taxes & fees

18 Oct - 19 Oct

A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

3. La Jolla Resort

Matecumbe

Brett

includes taxes & fees

14 Oct - 15 Oct

A covered outdoor area with a wooden deck, palm trees, and a view of the beach.

4. Breezy Palms Resort

Matecumbe

Gavin

includes taxes & fees

14 Oct - 15 Oct

A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.

5. Amara Cay Resort

Matecumbe

Danielle

includes taxes & fees

20 Oct - 21 Oct

A bathroom with a large bathtub, a view of the sea, and a pier with boats.

6. Cheeca Lodge & Spa

Matecumbe

Morgan

includes taxes & fees

19 Oct - 20 Oct

A balcony with a view of a beach, a pool, and a thatched-roof structure.

7. Hadley Resort and Marina

Matecumbe

weder

includes taxes & fees

9 Nov - 10 Nov

A resort with a pool surrounded by palm trees and a view of the ocean.

8. La Siesta Resort & Villas

Matecumbe

Brianne

includes taxes & fees

8 Nov - 9 Nov

A beachside resort with a pool area, lounge chairs, and palm trees.

9. Pines & Palms Resort

Matecumbe

Colt

includes taxes & fees

14 Oct - 15 Oct

A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

10. The Islands of Islamorada

Matecumbe

Christian

includes taxes & fees

14 Oct - 15 Oct

An outdoor dining area with wooden furniture, tables, and chairs, overlooking a beach and ocean.

11. Bayside Villas by Islander Resort

Matecumbe

Brian

includes taxes & fees

19 Oct - 20 Oct

A wooden deck with a view of the beach and ocean.

12. Sands of Islamorada

Matecumbe

Nicolas

includes taxes & fees

26 Oct - 27 Oct

A view from a window overlooking a beach with palm trees and a wooden pier.

13. Casa Morada

Matecumbe

David

includes taxes & fees

28 Oct - 29 Oct

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Top Upper Matecumbe Key Hotel Reviews

The Pelican Key Largo Cottages

8/10 Good

"The hotel’s location is fantastic, right on the Gulf side with its own private beach, lounge chairs, and even a small pier. The sunsets were absolutely stunning, and waking up by the water was a real treat. Just a heads up: we booked the economy double room and it was really small; barely enough space for two people and luggage. Still, the outdoor areas more than made up for it."

Find out more about Upper Matecumbe Key