Holiday rentals with beach access in Windley Key

Very nice condo in key colony beach, affordable, great stay for a family. Clean rooms, nice pool, nice private beach area, will bring family down again.

What an amazing location and you can really tell the host has thoughtfully designed the Airbnb, making it an experience. Will be back!

Norma was the most responsive host I’ve ever encountered. Her replies were prompt and she provided outstanding recommendations for local restaurants and entertainment. She checked in with us frequently. Her rental is adorably nautical, clean and well-maintained. I loved her style! She made sure we had everything we needed.

When I say that this is the most perfect Airbnb I’ve ever stayed in, I am not joking. Tina’s place is a gem in the upper Keys. Super close to John Pennekamp State park, good restaurants, and even better bars. I was able to show family who had never been to the Keys just how beautiful it truly is. Tina’s place drove that point home! I can’t wait until I have the chance to stay here again!

lots to do. beautiful pool

Perfect spot for a long weekend beach getaway! This was our first time visiting the Florida Keys, and we loved being right on the water with a small beach area to ourselves. The space was ideal for our group of friends, and the location was great—close to local bars and restaurants, some within walking distance or just a short drive away.

This is a beautiful condo in a great community. My 3 teens loved hanging out at the pool and the beach area. The bar on premises was an added perk and had a great menu.

This was our first family trip to the Keys and this location in Marathon was ideal! The condo was welcoming, beautiful and spacious for our family of 3. The balcony was our favorite place, which overlooked the pool and the seashore. The beach was lovely for shorter walks and just "being" with the ocean. Fun seashells & hermit crabs at low tide! Lots to do in the area -- definitely hoping to return next year. Mike was fantastic host & super helpful with questions.

SUPER CLEAN & exactly as the picture show! Loved having the golf cart assessable and the grounds are spectacular! Nice swimming pool and fishing and Lagoon! My family had an excellent stay!

This is the perfect location for us, we have a small flats boat and there’s great fishing in the area. The weather was not great but were able to find areas to fish sheltered from the wind. When not fishing, hanging out on the dock with Princess, watching the manatees and having a cold drink was absolute paradise. Penny is very responsive and was available anytime needed. This was our second time staying at this location and already talking about booking a longer stay next year.

Fantastic stay. Bryant was an excellent host and very responsive and accommodating

We had a great stay at Loretta’s place. The location offered a good jumping off point to explore the keys. The beach nearby along with canal access and kayaks was a huge plus. The garden area was nice though the mosquitos were intense. The place accommodated our group of 7 ppl well and everything was clean and well furnished. Overall, the place worked great for our group and we’d stay again!

We had an amazing family weekend here! The home was spotlessly clean, beautifully maintained, and incredibly well equipped with everything we needed. The ping pong table, video games, and sail kayaks were huge hits with the whole family. We also rented a boat, and having a private dock made that experience seamless and unforgettable. The location was quiet, safe, and perfect for quality time—cozy enough to relax, yet close to everything we needed. It truly felt like a home away from home. For all the amenities and the exceptional condition of the property, the price was a fantastic value. We’ve stayed in many vacation rentals, but this one stands out as one of the best. We’re already looking forward to coming back. Highly recommended!

The home is beautiful, well maintained, clean and perfectly set up for a large group. The house had literally everything we wanted plus additional thoughtful things that made our experience great! And.. All the amenities were just short a walk away. The host Joseph was very responsive and accommodating. Our family loved it here and will definitely return.

Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.

This was a great place for our family. We had plenty of space to relax. The home is well stocked with linens, kitchen items and paper goods. We only had to buy groceries. The tvs had streaming services and there are two types of coffee makers!

Swift response and resolution to a broken essential in the condo. Very responsive and timely communication. Would stay again.

Pedro was an amazing host! We got in a little early and thought we were going to need to check in early and he was very accommodating! I had a few questions and he responded almost immediately which is more than impressive! The place is perfectly decorated, had a very homey feeling to it and everything we needed.

Great, clean and well organized apartment. Great little pool a good beach and some restaurants and bars in walkable distance. Yuni responded very quickly to our messages and took care of the online little thing that wasn’t perfect right away. The location on marathon is also great as there are many things to do and see in a 5-10 minute drive. Great stay. Would absolutely do again and recommend. Thank you Yuni!

Great place for a family vacation, and perfect for kids! The lagoon is extremely convenient and fun for everyone. The fire pits and jetty are great for fishing and a relaxing night. The condo was just as pictured, extremely clean, and has everything you could need and more. It is located just around the corner from a ton of amazing restaurants. Would definitely come back again!

The condo was very nice. Lots of room, clean and easy to access. We loved the balcony, and spent a lot of time there. We enjoyed the kayaks a couple of different times as well. Our first time to The Keys and we enjoyed this spot.

We had a fantastic stay at this condo in Tavernier! The location was ideal—close to everything we wanted to see and do in the Keys. The unit was clean, comfortable, and well-stocked, with a beautiful view of the ocean that made every morning feel like a dream. The host was extremely responsive and made everything easy from check-in to check-out. Highly recommend this place—we’d love to come back!

I cannot say enough about how much we enjoyed our stay at Sangria Sunrise! The condo itself is beautiful, the property is awesome, well-maintained, and the staff are friendly and helpful! We spent most of our time at the pool and the beach. The pool bar is great and the pool is clean and refreshing. Plenty of sunny spots and lots of shaded tables, too. It’s right across from the condo so we went multiple times a day. Beautiful landscaping all around. The beach and marina area are really nice. We loved watching the boats from the balcony and seeing the sunrise over the water. Lots of fun things to do in the area within a short drive, but also plenty to do on the property if you prefer to stay put. Tracy is an excellent host and is very helpful and responsive. We will absolutely be back. Thank you for sharing your space with us, Tracy!

We were very happy to stay at Sunny's nice condo. It had everything we needed. This is a great location to explore the upper keys, John Pennykamp State Park is very near. It makes a perfect place to stay going to or from Key West. There is a tiny distant view of the ocean, but a lovely view of Mangrove Forest. You can sit on the little balcony and watch the sunrise, there are lots of birds to enjoy too. It is quiet and peaceful. The pool is nice, the grounds are clean and well maintained. There is a small beach and marina, and a good restaurant at the marina. We tried the coconut shrimp and it was delicious.