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

Windley Key Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Windley Key vacation rentals

A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

1. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (175 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
The price is ₩146,219
₩356,484 total
includes taxes & fees
Sep 28 - Sep 29
Treasure Harbor
A beach with palm trees, thatched-roof huts, and lounge chairs.

2. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (753 reviews)
"Great Florida style resort, clean and nice staff. Close to everything in Islamorada!"
United States
Debra
The price is ₩111,668
₩147,429 total
includes taxes & fees
Oct 1 - Oct 2
Breezy Palms Resort
A beachside lounge with wooden lounge chairs and blue umbrellas, overlooking a calm sea and docked boats.

3. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
9.8 out of 10, Exceptional, (183 reviews)
"Amazing vacation spot!!"
United States
Katie Lyn
The price is ₩273,836
₩308,067 total
includes taxes & fees
Sep 29 - Sep 30
Island Bay Resort
A floating house with a thatched roof, large sliding glass doors, and a wooden deck with a chair.

4. Premium Floating Bungalow by Stay Ombi

Premium Floating Bungalow by Stay Ombi
3.5 star property
Key Largo
9.6 out of 10, Exceptional, (4 reviews)
"Great experience ! Will do it again"
United States
Deivys
The price is ₩1,123,362
₩1,263,782 total
includes taxes & fees
Oct 6 - Oct 7
Premium Floating Bungalow by Stay Ombi
A balcony with a view of the sea, a dining area with chairs and a table, and a ceiling fan.

5. Beach Residence Private Overwater Dock Heated Pool Mahi Key

Beach Residence Private Overwater Dock Heated Pool Mahi Key
2.0 star property
Matecumbe
The price is ₩2,009,271
₩3,423,910 total
includes taxes & fees
Oct 14 - Oct 15
Beach Residence Private Overwater Dock Heated Pool Mahi Key
A beach with thatched umbrellas, lounge chairs, and a clear view of the ocean.

6. Kings Kamp

Kings Kamp
2.5 star property
Key Largo
8.6 out of 10, Excellent, (41 reviews)
"It was very nice!!"
United States
Michelle
The price is ₩275,234
₩309,639 total
includes taxes & fees
Sep 26 - Sep 27
Kings Kamp
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

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent
"Amando este lugar muchas gracias Yoli por toda la atención volveremos pronto"
isoruma 1-night trip
Posted 15 hours ago
Playa Largo Resort & Spa, Autograph Collection

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