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

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Windley Key holiday rentals

A covered outdoor area with a wooden deck, palm trees, and a view of the beach.

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (780 reviews)
"Such a great place to stay!!"
United States
Gavin
The price is ฿2,313
฿4,337 total
includes taxes & fees
10 Nov - 11 Nov
Breezy Palms Resort
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (181 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
United States
Diane
The price is ฿3,599
฿8,774 total
includes taxes & fees
8 Nov - 9 Nov
Treasure Harbor
A beachfront property with a wooden building, outdoor seating, and palm trees.

3. Kings Kamp

Kings Kamp
2.5 star property
Key Largo
8.6 out of 10, Excellent, (42 reviews)
"It was very nice!!"
United States
Michelle
The price is ฿10,090
฿11,351 total
includes taxes & fees
9 Nov - 10 Nov
Kings Kamp
A room with a bed, two chairs, and a view of a lake.

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 ฿23,823
฿26,801 total
includes taxes & fees
8 Nov - 9 Nov
Premium Floating Bungalow by Stay Ombi
Exterior

5. Piece of Paradise

Piece of Paradise
2.0 star property
Key largo
The price is ฿5,723
฿12,629 total
includes taxes & fees
1 Dec - 2 Dec
Piece of Paradise
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

Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"My husband and I had a wonderful stay! Our room had a small private balcony overlooking the pool, and the water - it was very peaceful. The restaurant next door was excellent and laid back - great place to eat after a day out exploring. the pool is zero entry - so can walk in from the side. they have a cute little sitting area downstairs that would be great to sit and play games - and fun hammocks and chairs by the water to sit and read, rest, or lay out in the sun. The resort is located about half way down the Keys - and was a great spot to use as a base to go out and explore during the day. I would stay here again in a heartbeat!"
Sara 2-night trip
Posted 12 hours ago
Lime Tree Bay Resort

Find out more about Windley Key

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