Pet-friendly holiday rentals in Windley Key

Christy was the best host! She was always available for quick questions and gave us great information as well. Her home was gorgeous! Beautifully decorated, flooring was luxurious and the space was perfect for the 2 us and our boat. The back porch was comfortable and the gas grill was a work of art! The boat ramp was a 1 mile away, Publix and Winn Dixie right around the corner and many restaurants all around made the location perfect for us. We had such a great stay and would definitely stay here again!! Thank You Christy for sharing your beautiful home with us!

The house was very cute, clean and comfortable. It was well-equipped for cooking, and had plenty of regular towels plus beach towels. We loved the outdoor space, particularly the screen porch. The hosts were super communicative - we had an issue with the shower head and they came and fixed it right away. Would recommend this spot!

Beautifully maintained, welcoming, peaceful and amazing outdoor entertaining pool area. Home is beautiful and provides enough space to entertain comfortably. Centrally located and wonderful restaurants to choose from. Would highly recommend this property. Maddie was very responsive and helpful. Will definitely rent again.

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!

Great place to stay for family vacation or guys fishing trip. Plenty of dock space to park the boat and easy access to the Atlantic. House is clean and all amenities worked as they should. Would definitely recommend to a family or friend. Mary was a great host who provided all information without even requesting it.

I’d like to start this review with JoAn is amazing and super responsive. If you need anything, she will ensure that you will get it. This house is the epitome of what you would expect for a Florida keys home. If you’re looking for a house with a lot of character, in a phenomenal location for Atlantic access and fuel, this is the place. We throughly enjoyed our time staying here and will be back next year. The pool was nice to get into after diving every day, there was a fresh water hose on the dock, a freshwater outside shower and even a fish cleaning station. There is a deep freezer for ice and a tiki bar outside with a sink. Couldn’t be any happier with the house or the host. Thanks again JoAn for letting us use your house.

We enjoyed our stay, the ground level is a fun place set up very well for children or pets, completely fenced to have no worries. Great view of the canal and direct access to run out of Pennekamp to the ocean side. Alejandro was very responsive and made everything easy

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!

Great place to stay. Really peaceful. Thank you!

Our family of five adults, plus two additional relatives, had the most incredible stay at this property. While we had planned several excursions, we found ourselves spending the majority of our seven-day trip enjoying everything this place had to offer. From fishing off the dock to kayaking and paddleboarding, the outdoor amenities were top-notch. The pool area was the perfect spot for relaxing and spending quality time together. One of the standout features was the amazing outdoor freezer—ideal for storing our fresh catch of Mahi from our charter trip. Inside, the kitchen was impressively well-equipped, making cooking a breeze. Every detail of the home was thoughtfully curated to provide comfort and convenience. This stay exceeded our expectations, and we’re already looking forward to returning. Highly recommend for anyone seeking a well-appointed, adventure-filled getaway!

The location was beautiful. The pictures were accurate. Andy was always helpful if we ever had any questions on anything that we needed.

Beautiful, well appointed home in the middle of the keys within driving distance to all the tourist attractions and restaurants. We are a 3 generation trip with grandparents and kids, and this house had it all! 3 bedrooms, each with excellent ocean views, great kitchen, kayaks and bikes in the garage, and incredible outdoor seating area! Highly recommended for families.

To begin with Niurka is a very sweet and nice person. I felt like we were family just by our communication. Her RV is the perfect location with everything you need! It was so clean, spacious and cozy. The surrounding areas are beautiful and you have everything you need to have an amazing time with your family. We will definitely be back to spend another weekend at Niurkas RV. Thank you for being such a great Host and always answering my calls. Gracias ❤️

The location and access to the beach and canal was amazing! We had such a fun time with the kayaks while being able to see all the wildlife and sail boats. The house was exactly what we needed. Jose was very helpful and flexible throughout our stay.

Larry was an excellent host who did everything to make the stay enjoyable. I would highly recommend staying at Larry's place and will definitely stay again if in the Marathon area.

This place was perfect for our small stay, we loved how well Alex communicated and he even came right over when I texted him to make him aware of something that was broke. He fixed it in 5 mins! He was extremely well at communicating and answered any questions we had.

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!

Key Lime Villa & Newman Hospitality were all around fantastic! We really enjoyed our weeklong stay at this beautiful property! They were a great host, very helpful and easy to deal with, super responsive too. The property itself was just as described, very nice, spacious and squeaky clean, very comfortable, we were able to settle in right away. Being big dog friendly was really nice as well, our boys were very comfortable and really enjoyed the place. We really love the pool and the fire pit area along with the dock area for sunset, it was very peaceful. Also, the location is perfect, it was right in the heart of the island so we were able to do a ton of walking to all of our restaurants and bars. We will definitely be back to stay here again for another trip soon! Thanks again to the team at Newman for making our stay a great one!

It was one of cleanliness Villas I have stayed in . We have been vacationing on Duck Key for 20 plus years and would definitely recommend 5085 - great location , very reasonable price and very simple easy check in and check out instructions. Thank you .

We had a wonderful stay at Playa Largo Ocean Residences. I came with my family to celebrate a milestone birthday and we all had a wonderful time! The house was even nicer than I had anticipated! It was modern, nicely furnished and very clean. We all had plenty of space as each bedroom has its own private bathroom. There was ample space in the common areas and we all really enjoyed hanging out on the third floor balcony. The hosts were quick to answer any questions via the Airbnb app. Having access to the Playa Largo Ocean Marriott was a huge plus as well. We spent an entire day there and rented a cabana by the pool (which I highly recommend). The pool and beach at the hotel were perfect and we stayed to eat dinner at the poolside restaurant which had excellent food. Afterward, they have free S’mores poolside which was a fun way to end the day. Would highly recommend this location and hope to stay again soon!

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!

Toni was very nice. She went out of her way to make sure we were satisfied with everything. The bed was comfortable and we got a great night's sleep there on the water. Watching the fish jump and pelicans dive as we sat on the front deck was very relaxing.

Location/ room was truly a 10/10!! The front desk representative was super helpful in accommodating us once we were unable to get into a our room due to the lock not working Great communication and customer service I would definitely stay here again 😍

Very nice townhouse, it was also really convenient to call the golf cart and go to the larger resort, which was beautiful.