A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Windley Key, Islamorada hotel rooms at the Hersha Hospitality

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Check prices for these dates

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Oct 8 - Oct 9
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Oct 9 - Oct 10
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Oct 9 - Oct 11
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Oct 16 - Oct 18
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Top Windley Key Hotel Reviews

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

10/10 Excellent
"Lovely and relaxed with free kayaks and stunning sunset views. We stayed here 10 years ago and we came back which didn't disappoint. Sharkys had great wings and fish dippers on happy hour and CCs pizza happy hour was amazing. Didnt bother with the restaurants next door as they were expensive. We saw a manatee and her calf at sunset down at the dock."
Keely 2-night trip
Posted 19 hours ago
The Pelican Key Largo Cottages
Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"Stayed for 2days. Pretty good experience with resort. Highly recommended."
Wenjing 1-night trip
Posted 20 hours ago
Waterside Suites & Marina
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

10/10 Excellent
"Book it you will like it"
anthony 3-night trip
Posted 21 hours ago
Fisher Inn Resort & Marina
Drop Anchor

Drop Anchor

10/10 Excellent
"Very clean property. Rooms well maintained and quiet."
Kelly 4-night trip
Posted 22 hours ago
Drop Anchor
Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Boo"
Francis X 5-night trip
Posted 23 hours ago
Chesapeake Beach Resort
Sunset Cove Beach Resort

Sunset Cove Beach Resort

10/10 Excellent
"Pet friendly"
John 2-night trip
Posted 23 hours ago
Sunset Cove Beach Resort
Reefhouse Resort & Marina

Reefhouse Resort & Marina

10/10 Excellent
"Está es mi segunda vez , visitando el resort, la atención es muy buena , la limpieza un 10 de 10 , la piscina tiene buen horario, Carlos en el mejor bartender , el único inconveniente es que cierran el bar muy temprano, porque ? Sería bueno que estuviera abierto hasta más tarde"
Malinayi 1-night trip
Posted 1 day ago
Reefhouse Resort & Marina
Islander Resort

Islander Resort

10/10 Excellent
"We got the poolside cabana king and it was perfect! Resort was immaculate! Already want to go back!"
Cheyenne 4-night trip
Posted 2 days ago
Islander Resort
Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Very clean resort. The pool was fabulous. The tiki bar was great. Stall friendly and helpful. Truly enjoyed my stay!"
Maureen 2-night trip
Posted 2 days ago
Amara Cay Resort

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