Pet-friendly holiday rentals in Windley Key

I loved it so much, I was already inquiring about a weekend so I could rebook! It was in a perfect location. I was able to Instacart and get Uber eats easily. The kitchen had everything I needed. It was very spacious and clean! Looking forward to going back.

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!

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.

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!

My parents, wife, and I booked a three day run at this spot. It was awesome! The location was perfect and Leila recommended a lot of places around to visit and eat. Fishing is active off of the back dock and most of the surrounding areas have lights set up, so there were plenty of fish to target all day. It is a quick drive to Key West and had some nice beaches within a 5 minute drive. One big plus is that the cut that this home is located on had minimal seaweed compared to most of the other areas. Overall, this is the perfect spot. We will definitely be back.

We had a wonderful time staying at Tim’s place! He was an excellent host who was always available if I had a question. The house is in a beautiful location. We enjoyed sitting on and fishing off the dock. The house had everything we needed for a fantastic stay and a very enjoyable vacation. I can’t say enough good things about our experience at the home. We were able to meet Tim and he was a lovely host. Thank you for a great vacation! We hope to come back in the future!

Great condo conveniently located in the heart of key Largo. Easy access to the ocean has kayaks or paddle boards available for use. The condo faces the saltwater lagoon great place to chill in the water and lots of fish to see. Norman gives great tour of the condo and the grounds. He was very responsive to our needs! Great place to stay!

Incredible for a family vacation. 🏝️The property feels very private, clean, well decorated, and many amenities. We tried out the paddle boards and spent a lot of time in the pool. When going to the beach, Aileen already had chairs and towels to bring! This property really is a gem. Thank you Aileen!

Very nice place, we enjoyed the pool and feeding fish in the lagoon. Didn’t try using the golf cart. The rental was clean and spacious,

I enjoyed my stay! The camper is beautiful and has a beautiful outside space to hang out. I loved that it was gated perfect for my toddler & my dogs. Host was very helpful too.

Beautiful ocean views and great local recommendations from the host! Some aspects of the interior were a bit dated, but with multiple areas to enjoy the outdoors (offering full shade to full sun and everything in between), we didn't do much inside except sleep. Kids spent hours per day in the pool and adults most enjoyed lounging on the jetty with 345 degrees of ocean views. Board games (and a ps3) were available for the occasional down time. The location allows for a feeling of privacy on the ocean while offering many hidden gems for dining and activities nearby.

Super cute home with lovely outdoor sitting spaces. Most of home updated with exception of bathrooms. Coffee pot did not fill completely but there was Keurig alternative. Limited number of washcloths available. Loved outdoor seating and really enjoyed watching all the birds and wildlife. Excellent location close to many activities

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!

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.

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.

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!

Beautiful home with amazing access to amenities

I want to start off by saying Newman Hospitality has some of the best customer service I’ve ever experienced. Easy to work with and great communication. The Airbnb was perfect, clean, and close to everything! The only issue (small issue) is the boat dockage. The water is very shallow so renters should be an extremely cautious if they are renting a slip.

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 .

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!

Beautiful place on Islamorada halfway between Key West and Fort Lauderdale...so peaceful and great views... the heated pool was also very nice... the Lavazza coffee maker made our morning since its not really a place you can walk to/from... there is a flight of stairs just in case you have mobility issues... bathroom amenities are very nice!

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 😍

House was beautiful and so homy! The place is modern and it’s what i loved most about it! I will definitely be staying there again no hesitation on my next trip! Thank you Yailin!