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

Tonight
Sep 22 - Sep 23
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Sep 23 - Sep 24
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Sep 25 - Sep 27
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Oct 2 - Oct 4
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Top Windley 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 3 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 5 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
Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay

10/10 Excellent
"Nice place"
Travis 1-night trip
Posted 18 hours ago
Hampton Inn Key Largo Manatee Bay
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 21 hours ago
The Pelican Key Largo Cottages
Bayside Inn Key Largo

Bayside Inn Key Largo

10/10 Excellent
"We stayed here for 2 nights and chose this hotel for the proximity to the dive shop we were diving with on their boat. It was a good choice with clean rooms and nice staff. Bonus SNOOKS restaurant & Tiki Bar right on the water! We would stay here again!"
Jamie 2-night trip
Posted 22 hours ago
Bayside Inn Key Largo
Rock Reef Resort

Rock Reef Resort

10/10 Excellent
"Un lugar en el que se respira paz y tranquilidad. Respeto al silencio. Sencillo y acogedor. Magnífico para descansar y recargar baterías. Y para los que les guste, observar la hermosa puesta y salida del Sol sobre el mar, en un entorno natural. Ideal para parejas."
Ricardo 3-night trip
Posted 23 hours ago
Rock Reef Resort
Islander Resort

Islander Resort

10/10 Excellent
"Nice pool"
Henry 1-night trip
Posted 1 day ago
Islander Resort
Reefhouse Resort & Marina

Reefhouse Resort & Marina

10/10 Excellent
"Opal takes pride ownership in running a customer service excellence resort The champagne touch is nice Thank you Dr Fajardo Garcia"
Onelia 1-night trip
Posted 1 day ago
Reefhouse Resort & Marina

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