
Holiday rentals in Windley Key
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Top-rated holiday rentals in Windley Key
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Other great holiday rentals in Windley Key

Villa in Islamorada
5 out of 5 average rating, 3 reviewsThe Nest Villa & Marina in the heart of Islamorada
JoanneRating, 5 stars1 week ago
This was our second stay at The Nest and we will be back! The interior is so soothing, comfortable, clean and very well stocked. Communication with the host was great and they were very responsive to questions. The surroundings are beautiful and peaceful, and the HUGE patio was so perfect for relaxing at the end of the day. Can’t wait to go back!
Guest favourite

Villa in Islamorada
5 out of 5 average rating, 35 reviewsAnglers Reef Islamorada
KatherineRating, 5 stars1 month ago
What a great place to stay! The community was well kept and the amenities were wonderful. There are great restaurants close by and it's location is perfect. We had a wonderful time and met some really wonderful people. We plan on returning, next year!

Home in Islamorada
5 out of 5 average rating, 3 reviewsCasa del Mar Retreat- June-December availability
AmyRating, 5 stars2 months ago
It was the perfect get away for my daughter and I and a few friends. The house was gorgeous. The pool was so relaxing. The pier was a great location to spend time and watch the wildlife in the ocean below. The location was super convenient to shops and restaurants and lots of activities. Ani was super communicative - offering to help connect us with tours and answering questions. It was hard to leave and we will definitely be back. Thanks for a great week!!!

Flat in Islamorada
4.78 out of 5 average rating, 46 reviewsPoolside 2 queen Apartment
ElizabethRating, 5 stars2 weeks 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 Marathon
5 out of 5 average rating, 4 reviewsThe Roseate House at Grassy Key
MollyRating, 5 stars2 weeks ago
I don’t even know where to begin. From start to finish, our stay was absolute perfection. The views could not be beat. There are kayaks to venture out into the gulf and the mangroves, a pool that’s COOLED (you know how hot pools can get during the summer. It was so refreshing) and a garden oasis full of some of the most beautiful foliage I’ve ever seen. I’m from Charleston, SC. I’m used to waterfront living, but this was just something more magical than I could’ve ever predicted. I’m already planning my trip back for next year. Heidi left a great list of recs for restaurants and activities to do, but the property was so incredible, I only left to eat really. If you’re looking for a relaxing place to stay, with on site water days this is the place for you. The house is nice, but also has that old school beach vibe which is my absolute favorite. I just can’t say enough good things. Thank you so much, Heidi, for sharing your stunning home with us.
Guest favourite

Villa in Key Largo
4.87 out of 5 average rating, 15 reviews4-Bed Spring Break Villa: Clubhouse, Pool&Marriott
IsaiasRating, 5 stars3 days ago
Words can’t describe how amazing the unit was. The pictures don’t do any justice. When I arrived I reached out to Josie for further instructions and she quickly responded. Upon entering the unit we immediately felt the warmth and welcome. I would recommend to any family of 8 in Key Largo area.

Home in Islamorada
4.93 out of 5 average rating, 27 reviewsIslamorada 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 reviewsOceanside 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!
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Bahia Honda State Park
- Coral Castle
- Cannon Beach
- Biscayne National Park
- Conch Key
- Calusa Beach & Loggerhead Beach
- Everglades Alligator Farm
- Theater of the Sea
- Cocoa Plum Beach
- EAA Air Museum
- Horseshoe Beach
- Sea Oats Beach
- Monkey Jungle
- Far Beach
- Deering Estate
- Windley Key Fossil Reef Geological State Park
- Long Key State Park
- Keys' Meads