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

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Windley Key guest houses

A beachside lounge with a thatched roof, lounge chairs, and a view of the ocean.

1. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.6 out of 10, Exceptional, (280 reviews)
"Incredible place, ample room and everything you need to cook and to bbq."
United States
Nathalie
The price is NZ$237
includes taxes & fees
18 Nov - 19 Nov
Ragged Edge Resort & Marina
A clear blue pool surrounded by palm trees and a bridge in the background.

2. Charming Suite @Islamorada With Pool Access - Twilight Suite

Charming Suite @Islamorada With Pool Access - Twilight Suite
Matecumbe
The price is NZ$4,277
includes taxes & fees
15 Dec - 16 Dec
Charming Suite @Islamorada With Pool Access - Twilight Suite
An indoor wooden structure with a thatched roof, multiple hanging spherical lights, and a central seating area.

3. Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
Matecumbe
The price is NZ$4,294
includes taxes & fees
21 Nov - 22 Nov
Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
A clear blue pool surrounded by palm trees and a bridge in the background.

4. Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite

Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
Matecumbe
The price is NZ$4,060
includes taxes & fees
15 Dec - 16 Dec
Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
A deck with a white railing, a lounge chair, a blue towel, and a large umbrella.

5. Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room

Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
Matecumbe
The price is NZ$2,099
includes taxes & fees
22 Nov - 23 Nov
Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
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.
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Top Windley Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

8/10 Good
"The room was clean and felt newly renovated. The shower door is farm slide style glass that is very heavy and difficult to use. There is not much sound insulation between the rooms. Our upstairs neighbors were very loud and were up super early which caused us to lose sleep. Not the hotels fault but annoying regardless. The location was great and very close to numerous activities and restaurants."
Robert 3-night trip
Posted 12 hours ago
Chesapeake Beach Resort

Find out more about Windley Key

Windley Key Guest Houses information

Number of reviews
Accommodation
4 Guest Houses
Lowest Price
NZ$237
Highest Price
NZ$4,294

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