Holiday Homes in Windley Key

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Featured Holiday Homes in Windley Key

Relax by the serene pool surrounded by lush greenery and palm trees.

"The property is central location in Islamorada, best location....The outdoor area is perfect,pool heated very enjoyable.. great neighborhood..Friendly Host JoAnn is amazing, and prompt response, a delightful person, and a wonderful host!"

Kitchen features a central island with a countertop, surrounded by cabinetry and a refrigerator, microwave, and oven.

"Amazing spot in the Keys. Stayed there the weekend for a wedding in Tavernier and was close to everything we needed. Would definitely stay here again when I come back. "

includes taxes & fees

13 Aug - 14 Aug

Relax in this serene beachside retreat with an outdoor space featuring a wicker table and chairs.

"Everything just great except need better vaccum"

Kayak rentals available at Key Largo's marina, where you can launch your fishing adventure.

"Great tiny house, enjoyed our stay"

includes taxes & fees

10 Aug - 11 Aug

Relax by the pool surrounded by lush greenery and palm trees, with lounge chairs and umbrellas nearby.

"This condo and the club is awesome. The pool is wonderful. We loved everything about or stay would come back! "

Relax by the clear blue pool surrounded by palm trees and a building with balconies.

"We had a Wonderful time! There was plenty of space for our family of five. We had a few minor issues with ants, but it did not impact our comfortable stay. We loved the pool and Pickleball court! Would highly recommend. "

"Beautiful property with a lot of space. Very well stocked with more than what you even think you need. Mariners Club is very nice with two great pools, a game room, marina, and pickleball courts. Only thing to note is there’s no beach access if that’s what you are looking for."

Surrounded by lush greenery and a serene water body, this resort offers a tranquil retreat amidst a tropical setting.

"Such a great little property in a awesome community! A from the host he was such a nice person and communicating was superior would definitely rent again! "

Relax by the pool surrounded by palm trees and lounge chairs.

"Clean , beautiful location and pools . "

Relax by the serene waterfront, where a dock invites you to unwind with a meal or a moment of tranquility.

"Best sunrise site."

includes taxes & fees

25 Aug - 26 Aug

Relax by the pool surrounded by lush greenery and palm trees, with lounge chairs and umbrellas providing ample seating and shade.

"Nice location with lots of restaurant choices, pools and especially the Grotto were awesome, Tarpon feeding was our favorite nearby activity."

includes taxes & fees

10 Aug - 11 Aug

"My wife and I stayed here for our honeymoon , and we were absolutely thrilled with everything. We loved that the house had a bunch of mini splits to keep it nice and chilly. We also loved that the house was very clean and well kept. The tiki hut on the water with the tv and great lighting at night makes a perfect place to relax at the end of a fun filled day. All around this was a fantastic place to stay!"

includes taxes & fees

8 Sept - 9 Sept

Relax by the serene waterfront with a covered seating area and tranquil views.

"We had a great stay! We loved having kayaks, snorkels, a lagoon and the ocean and everything nearby. We loved feeding the fish on the property. The kitchen is well stocked with everything we needed for making meals. Nice restaurants nearby! Thanks for meeting us, Norman - that was very helpful!!"

Relax by the pool under the stars, surrounded by lush trees and a thatched-roof structure.

"We have stayed in one of this Hosts properties for 5 years in a row. Always clean, always great communication and we always have a great time. We highly recommend."

Relax in a shaded beachside haven with a thatched-roof structure, comfortable seating, and stunning ocean views.

"The porperty had everything we needed for a great family spring break. The kids especially enjoyed trips to the jetty on the golf cart!"

Relax by the central pool surrounded by lush greenery and palm trees, with sun loungers and umbrellas at your disposal.

"We stayed at this property for our spring break trip and thoroughly enjoyed our stay. The home was clean, comfortable, and well-equipped with everything we needed. The location was great—close to local attractions yet peaceful enough for a relaxing getaway. The host was responsive and accommodating, making the entire experience seamless. We would definitely stay here again!"

Relax in style with comfortable sofas and chairs, a hot tub, and a shaded seating area surrounded by palm trees.

"We loved this house! Plenty of room, wonderful location. Super clean and the outdoor space was awesome! Hot tub, BBQ and plenty of toys to enjoy the lagoon❤️"

includes taxes & fees

17 Aug - 18 Aug

Relax by the pool surrounded by palm trees and enjoy the serene atmosphere.

"The unit was set up perfect for my family as well as my brother-in-law‘s for a family wedding in Key Largo. The pools were beautiful. The property was well maintained and we had a wonderful time. "