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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Villas in Windley Key

The Islands of Islamorada
Relax by the pool surrounded by palm trees and enjoy stunning ocean views.

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (65)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is RM2,332
RM2,859 total
includes taxes & fees
6 Aug - 7 Aug
The Islands of Islamorada
Waterfront House with Boat Dock
Relax on the spacious balcony with a sofa set and individual chairs, overlooking a serene landscape.

Waterfront House with Boat Dock

5.0 star property
6.0 out of 10, (1)
"Covered porch was nice for time outside. Inside was in need of work. Closets unfinished, no place to put any luggage, advertises a king bed and a queen bed, but only had a king and a full, no tp, or tissue products when we arrived. None of the above were deal breakers but just allot of small things that add up to frustration."
Waterfront House with Boat Dock
Anglers Reef Villa 1
Stunning beachfront hotels with inviting porches and beautifully landscaped grounds.

Anglers Reef Villa 1

3.5 star property
9.4 out of 10, Exceptional, (3)
"The property is centrally located, so it's very easy to get to all of the keys. The layout is excellent and is very well stocked with everything you will need. The pool on the property is fantastic with a great view. Communication with the owner is fantastic. We would definitely go here again and highly recommend it."
Anglers Reef Villa 1
Midnight Runner in Islamorada
Relax by the serene pool, surrounded by lush greenery and palm trees, with lounge chairs and umbrellas providing shade.

Midnight Runner in Islamorada

2.0 star property
Midnight Runner in Islamorada
The Salty B in Islamorada
Stunning two-story home with a balcony and garage.

The Salty B in Islamorada

2.0 star property
The Salty B in Islamorada
The Caribbean Resort Royal Palm South
Relax in a serene ocean-view setting with a wicker sofa and chairs.

The Caribbean Resort Royal Palm South

3.5 star property
The Caribbean Resort Royal Palm South
Turtle Nest Estate in Islamorada
Relax on the beachfront deck with a pool and lounge chairs, surrounded by palm trees and a white fence.

Turtle Nest Estate in Islamorada

2.0 star property
Turtle Nest Estate in Islamorada
Island Palm Estate in Islamorada
Relax by the serene pool surrounded by tall palm trees and enjoy the ocean views.

Island Palm Estate in Islamorada

2.0 star property
Island Palm Estate in Islamorada
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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