Holiday houses in Windley Key

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Popular amenities for Windley Key holiday rentals

Other great holiday rentals in Windley Key

Guest favourite
Villa in Islamorada
5 out of 5 average rating, 34 reviews

Anglers Reef Islamorada

DeborahRating, 5 stars1 month ago
We had never been to the Keys before and were not sure where to stay. Islamorada ended up being an excellent choice. There was a great variety of activities nearby, and within a 30-45 minute drive there were even more unique places to visit. The private community where Gina's house is located feels like a mini-resort that The Mouse would be proud of. The community was clean, the staff were extremely friendly, and the other people we met were all gracious. Gina's house was well located - close to the entrance and a 1-minute walk to the pool. The house was super clean, comfortable, and the few things we had questions about were immediately dealt with by Gina. We're considering another trip to the Keys and would not hesitate to stay here again or recommend it to another group.
Apartment in Tavernier
5 out of 5 average rating, 4 reviews

Superb Ocean View w/heated pool, beach, tennis

JustinRating, 5 stars2 months ago
Great location. It felt very quiet and peaceful. We didn't have the best weather so we didn't get to enjoy all the amenities of the property but it felt walkable.
Apartment in Islamorada
4.78 out of 5 average rating, 46 reviews

Poolside 2 queen Apartment

ElizabethRating, 5 stars1 week ago
We had a great time at Breezy Palms with just me and my daughter! The poolside apartment was so squeaky clean, tidy, and just lovely. The bed was very comfortable. We had everything we needed. We will definitely be back with the entire family.
Home in Islamorada
4.93 out of 5 average rating, 27 reviews

Islamorada 131 Anglers Reef Ocean Community 2/2.5

JaredRating, 5 stars2 months ago
We really enjoyed our stay at 131 Anglers Reef. The neighborhood was quiet and beautiful, and the community pool was a great bonus. The house itself was clean, well-maintained, and spacious enough for our family. During our stay, we rented a boat for the day from A1 Watersports — definitely one of the highlights of our trip! We also took a day trip to Key West and visited Fort Zachary Taylor State Park. The beach there was perfect for snorkeling and offered a fun change of scenery. Founders Park was just down the road. It’s a fantastic beach for all ages, especially for families with small kids.
Guest favourite
Home in Key Largo
5 out of 5 average rating, 20 reviews

Oceanside Paradise - Pool, HotTub, Kayaks, Pets OK

HannahRating, 5 stars2 weeks ago
Awesome modern home in a little, upcoming community. Pool was great place to relax. If you're up early enough to catch the sunrise they are breathtaking! You might spot a small nurse shark or tarpon in the water!
Top Guest favourite
Townhouse in Islamorada
5 out of 5 average rating, 9 reviews

NEW Oceanfront, Gameroom, Dockage - Paradise Palms

AndreaRating, 5 stars6 days ago
This house was so comfortable and accommodating! The weather was bad the first 4 days of our trip and it was so nice to have the game room to keep us entertained! Everything you need and more!
Top Guest favourite
Condo in Tavernier
5 out of 5 average rating, 5 reviews

Oceanfront 2 bdrm, 2 bath, View, Pool, Islamorada

MichalRating, 5 stars6 months ago
We stayed here for the Thanksgiving week. The place was nice, clean, and quiet. My kids enjoyed the playroom and the pool. The condo had plenty of board games to keep the kids entertained. The Keys have lots to offer, so there is always plenty to do. Donna was very responsive, the check-in was very simple, and we had a great time. Thank you for hosting us.
Guest favourite
Home in Islamorada
4.85 out of 5 average rating, 60 reviews

Oceanfront community 114 Anglers Reef Islamorada

MarkRating, 5 stars1 month ago
We absolutely loved Jennifer’s home! The house was so clean and had everything we needed included towels, kid’s toys and even baby gates for the stairs. The pool was so perfect and we had a blast swimming every day. We highly recommend staying at this beautiful property and will be visiting again!

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada
  6. Windley Key