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Check prices for these dates

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Sep 5 - Sep 7
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Sep 19 - Sep 21
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Oct 17 - Oct 19
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Nov 14 - Nov 16

Villas in Windley Key

Our top choices for Windley Key villas

The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (66)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is ₩769,610
₩942,947 total
includes taxes & fees
Aug 23 - Aug 24
The Islands of Islamorada
Waterfront House with Boat Dock
Terrace/patio

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
Property 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
The Caribbean Resort Royal Palm South
Outdoor pool

The Caribbean Resort Royal Palm South

3.5 star property
The Caribbean Resort Royal Palm South
The Salty B in Islamorada
Villa | 2 bedrooms

The Salty B in Islamorada

2.0 star property
The Salty B in Islamorada
Midnight Runner in Islamorada
Villa

Midnight Runner in Islamorada

2.0 star property
Midnight Runner in Islamorada
Turtle Nest Estate in Islamorada
Villa | 4 bedrooms

Turtle Nest Estate in Islamorada

2.0 star property
Turtle Nest Estate in Islamorada
Island Palm Estate in Islamorada
Villa | 10 bedrooms

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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Top Windley Key Hotel Reviews

Drop Anchor

Drop Anchor

10/10 Excellent
"Liked the Atlantic bulkhead. Plenty of dock space and casting room. Tasteful atmosphere with clean grounds and pool. Boat launch looked safe and maintained. Outdoor lights gave a nice ambience. Room was clean and properly stocked. TV was outdated."
STEPHEN 1-night trip
Posted 21 hours ago
Drop Anchor