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

Search Hotels by Hersha Hospitality in Upper Matecumbe Key

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Check prices for these dates

Tonight
22 Sept - 23 Sept
Tomorrow
23 Sept - 24 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct
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Top Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Great beach for the keys and great breakfast! The bar food is minimal and they don’t always open but Wahoo next door is amazing. Would definitely come back to this hotel."
Julia 1-night trip
Posted 4 hours ago
Chesapeake Beach Resort
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent
"Todo perfecto solo q en los Restaurantes no hay desayuno incluido, y los Plato’s están por en ima de la media de sus precios y en realidad no vale la pens pagarlos en ima de eso se demoran mucho"
Raul 2-night trip
Posted 6 hours ago
Playa Largo Resort & Spa, Autograph Collection
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

8/10 Good
"All was great, we just had an issue with a food item we ordered twice and was incorrectly doubled charged in both occasions. It looked liked a POS system issue, and the staff quickly resolved it. Other than that, everyone and everything was great. The resort is paradise by the beach ⛱️ 💯"
Luciana 1-night trip
Posted 6 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Casa Morada

Casa Morada

10/10 Excellent
"Very helpful staff and great location"
David 1-night trip
Posted 7 hours ago
Casa Morada
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

10/10 Excellent
"The Pelican is a darling spot! Lots of space, convenient parking right next to our door, beautiful sandy beach area, well maintained dock, plenty of comfy Adirondack chairs in multiple spots to watch the water - the boats, fish, birds, and manatees. We really enjoyed the use of kayaks as well. Just a lovely property and stay."
Heidi 1-night trip
Posted 22 hours ago
The Pelican Key Largo Cottages
Islander Resort

Islander Resort

10/10 Excellent
"Nice pool"
Henry 1-night trip
Posted 1 day ago
Islander Resort
Hawks Cay Resort

Hawks Cay Resort

8/10 Good
"The village we were assigned has roaches and the main bedroom has the pain from the felling peeling which could be a hazard. Also, the water park that was supposed to be completed on September has a delay and that was the main reason a reserve this hotel."
Miladis 2-night trip
Posted 1 day ago
Hawks Cay Resort
Hadley Resort and Marina

Hadley Resort and Marina

10/10 Excellent
"Si quieres unas vacaciones increíbles , este es el lugar"
Yerisleidys 2-night trip
Posted 2 days ago
Hadley Resort and Marina
Breezy Palms Resort

Breezy Palms Resort

10/10 Excellent
"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."
Dionisio 1-night trip
Posted 3 days ago
Breezy Palms Resort

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