Vacation rentals in Windley Key
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Top-rated vacation rentals in Windley Key
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windley Key vacation rentals
Other great vacation rentals in Windley Key
Guest favorite
Bungalow in Islamorada
4.97 out of 5 average rating, 29 reviewsDream in Paradise! King Master, Queen Guest, Pool
Feb 4 – 11
$693 per night
Guest favorite
Home in Islamorada
4.94 out of 5 average rating, 16 reviews3 Lux Ensuites Walk/Boat Island!
Feb 22 – Mar 1
$495 per night
Guest favorite
Home in Key Largo
5.0 out of 5 average rating, 14 reviewsPrivate 1 Acre House~Private Beach~Tiki Hut~Dock
May 22 – 29
$700 per night
Guest favorite
Home in Key Largo
4.99 out of 5 average rating, 74 reviewsLittle Cottage on an island
Jul 22 – 29
$150 per night
Guest favorite
Cottage in Islamorada
4.97 out of 5 average rating, 65 reviewsKey Lime Cottage 2br 1ba w/pool
Oct 27 – Nov 3
$316 per night
Guest favorite
Condo in Tavernier
4.98 out of 5 average rating, 64 reviewsSugar Cane - Florida Keys tropical retreat
Sep 15 – 22
$179 per night
Guest favorite
Home in Key Largo
5.0 out of 5 average rating, 47 reviewsThe Paradise 2
Nov 30 – Dec 7
$325 per night
Guest favorite
Home in Marathon
4.97 out of 5 average rating, 32 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Mar 22 – 29
$543 per night
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