Vacation rentals with a pool in Windley Key

We really enjoyed our stay. It completely matched the description, the patio was amazing, and the place was well stocked with everything we needed. It had many personal touches which made us feel at home. It was a great fit for two adults and 2 kids. Our time on the porch in the morning and relaxing in the evenings were the best part. Highly recommend!

We had an absolutely wonderful stay here! It couldn’t have been any better. The house is laid out in a perfect way inside and out to make you just relax and enjoy the relaxed Key Largo way of life! There is an abundance of lovely towels for the bathroom as well as the pool, all showers are stocked with shower gels and soaps – it feels like a 5 star hotel! We appreciated all the personal touches very much. We love wildlife and we saw Manatees swim past us a few times, ospreys around us and such beautiful bird song. The layout allows you to enjoy the day downstairs on the deck in sun surrounded by palm trees and shade on the lovely outdoor seating area whatever you wish and the BBQ facility allows you to cook and enjoy the outdoor life. Upstairs has a great balcony place to sit outside at night around the table and enjoy dinner fully enclosed with mosquito netting so that you don’t get targeted or bitten. We loved our kayaking around the Mangroves and all the wildlife you can see

I am typically not an Airbnb person, as I prefer a hotel. This home was better than any resort we could’ve stayed at. Check in was simple. The home was beautiful. The location was perfect. Our favorite part was the second space that was separate from the main house. We are a family of four (mom, dad and two kids) who were traveling with my sister. She was able to have her own space with a private bathroom and entrance and could “go home” when the craziness of two kids was enough. Both units were adequately stocked with towels and linens. The kitchens had anything you could need including coffee maker, blender, toaster, pots and pans. The pool and hot tub were incredible! So much so, that we took two full days and only left for dinner! Sean and Denise were great hosts and super responsive! We will be back.

We had a great time at Cary’s Oceanside! Beautiful location, beautiful and comfortable accommodations! Maria was very helpful and responsive with our questions. We really enjoyed the pool and outdoor area.

We had six adults in our group and the house was a perfect location to go out fishing or to the beach. The house was well stocked and with plenty of linens and beach towels. We rented a boat for three days from Tropical boat rentals and the canal location made fishing super easy. Access to the ocean or the bay was convenient. We even caught several fish in the canal. We saw manatees, sharks, manna rays and tons of fish while enjoying the swimming pool. We can’t wait to make a return trip.

This was the most perfect Airbnb for our vacation. First of all, Marathon is the perfect location if you are looking to explore multiple parts of the Keys. 1 hour to Key Largo, 1 hour to Key West. We could not have asked for a better location. The home looks just like the photos and was perfect for our family of 4 + our pup. The beds were comfortable, the living space had plenty of room for our crew, but the real show stopper was the pool. If we weren't out and about exploring the Keys, we were definitely in/by the pool! A few added bonuses: (1) K-cups for our use for that first morning. This kept us from having to worry about an emergency grocery store trip the evening of our arrival (2) pool floats available for our use (3) bikes & kayaks for everyone (4) EVERYTHING. We couldn't have asked for better - we will definitely be back!

It really is the perfect place to stay. We picked this house after our last trip to FL where we rented a beach house only to have high winds and man of war jellyfish so couldn't get in the water at all. This place with its amazing hot tub and pool, tons of pool toys and floaties, books and games, would be a wonderful vacation even if you were stuck there the whole time due to bad weather, These owners have done a wonderful job thinking of so many amenities- cozy couch blankets, life jackets, tons of beach equipment, so many dishes and pans and various drink holders. The only complaint I could think of if I had to would be to have another ice tray (there were two semi broken ones but not a big deal as we just bought ice). But that's a pretty small thing in the long list of things that were superb. Even the beds were as soft and as comfortable as mine at home. I hate to let the secret out, but this house is fantastic.

We had an amazing time! The location is perfect with so many things to do, pool, hot tub, canal, etc. The home was overall beautiful and we loved every second of it!

This place was great for an in between Miami and Key West! The pool was perfect for relaxing at all day! Restaurants near by were all fantastic! Doable drives for day trips to key west and Miami!

Stayed at Vanessa’s place twice while visiting the Keys. Quiet, clean and private. A great host and would definitely stay again next time a visit. Easy access to everything off the highway and great amenities with the pool and beach nearby. 10/10.

The home was immaculate, all the necessary dishes, pans, appliances. There were no extras such as coffee filters or cooking oils etc. The setting was very beautiful and well maintained and many amenities. It is a family friendly community with multiple young children. Location near restaurants and activities was great. And we really enjoyed the screened in porch. Thanks!

We had a great stay with our kids - the condo was well furnished, clean, and easily walkable to the pool, game room, and tennis courts. We appreciated the condo was stocked with “kid things” - pack and play, high chair, pool toys, and games. Would recommend to others!

Kimberly was a very responsive host providing clear instructions, local recommendations and checking in on our stay to see if she could help with anything else. The unit was clean and comfortable. Wish the deck was larger was our only negative. The community pool area was great to hang out at with plenty of chairs, lounges and umbrellas. And we enjoyed the poke bowl and cocktails at the on-site grill. Would stay again if in the area.

The unit is just like the photos and was very comfortable! John was helpful and helped make for an enjoyable stay! Would happily stay here again

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!

Very clean with beautiful view of the water. Matched the description accurately would definitely come again