Vacation rentals with beach access in Windley Key

We had a great time staying at this property. We liked it because it is very easy to get to, has it's own beach, and has plenty of room for a family. Key Colony is a real gem IMHO. We wanted a property that put us in a central location in the keys - 45 minutes to Islamadora, a little over an hournl from Key West, but in a place that is great for snorkeling and water activities. This place fits that perfectly. The property is easy to check into to, Yuni give a code in advance for the door. Parking is under the building in the shade (big plus) and right in front of the elevator. Super convenient! The kitchen is nice, we cooked meals on probably 3 nights. Beds were comfortable and there is a washer/dryer that is really nice to have on vacation. Great host for sure. If in the keys again I wouldn't hesitate to stay there again as it was a very positive experience.

Great stay with a very nice view of the sea! Host sent proactive instructions and the place was everything we wanted. Dennys Cuban Cafe was an excellent place to grab any meal of the day.

Place was nice and peaceful. We enjoyed the down time. Enjoyed laying on the beach and soaking up the sun. Only thing I can say negative is the tide was high and had lots of seaweed so u couldn’t get in the water but that’s out of ur control. Definitely somewhere we will return too in the future.

We loved the stay at Norma's place. Loved everything about it. It is functional, beautiful inside and outside, clean, well-stocked with everything and Norma could not have been more helpful throughout. Can't wait to come back again.

The rental was very spacious, nicely decorated, and extremely well cared for.

We had a great time at Diana’s place. We loved being able to use the available kayaks and fishing gear! Diana was super responsive and gave us some great recommendations. Moon bay was the perfect choice for our family of 5! Thanks Diana

Rhonda's place is terrific! Lovely location with full water views. Pool was excellent. The home was very comfortable, clean and convenient to restaurants and stores. Would definitely rent again.

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.

Everything was excellent. Only complaint would be the bicycles. One bike was usable but the seat was loose and we didn’t have tools to fix it. The other adult bike’s chain was rusted so bad it wasn’t usable. We still had an excellent experience.

We had a delightful time. The unit was clean & comfortable and easily accommodated our party of 5 adults. The balcony was very pleasant and had a great relaxing view. The shared beach was also very relaxing with plenty of chairs and a nice covered card table area. This is in addition to the multiple seating options at our private pool. Families were enjoying the provided kayaks of which there were plenty. Susan and Dale were extremely responsive to all of our inquiries including showing up to address an issue within 15 minutes! Overall we had a very pleasant stay.

We loved our stay at Jeffery's house. It is spacious and very comfortable. My husband appreciated the proximity to the pickleball courts - we could see them from our bedroom windows- and my son enjoyed fishing off the dock. The upper suite was wonderful for privacy and quiet when the older kids stayed up later than the adults. Jeffery was super helpful and responsive. We would love to stay here again!

We had a great time at Paradise Found. The property was lovely and clean, all very well maintained. The location was beautiful, backing onto the water and enormously peaceful, a great setting. Kari was very communicative and always responded quickly to any queries. Overall, we were very happy.

We thoroughly enjoyed our week at Matt’s place! As a host, Matt was quick to answer our questions and provide what we needed. The location is excellent, with the canal views from the back yard and a few minutes walk to the beach.

Alfonso is a very responsive host who provided clear details, local recommendations (multiple of which we used), and provided a place in a great location. Neighbors are friendly. Place was clean. Perfect for our family with a 14 and 6 year old.

The hosts were so accommodating and friendly. The space was newly remodeled with excellent quality and style of workmanship. It was also immaculately clean and incredibly well stocked. Our family of five (three young adult boys) was always comfortable. The hosts thought of everything you could want on vacation. They worked with us to make sure we had a place to dock and use our wave runners, there was outdoor dining and grilling space, complete with a filtered ice machine and an outdoor chest fridge for any fishing, a beautiful spot overlooking the canal, a pergola over the sitting area to provide extra shade, and the house itself was gorgeous and well appointed with plenty of space. We’d love to visit again!

Great attached townhome/duplex with privacy fence between the other side. Great private pool just on the canal! The bottom story was perfect for extended family to have privacy but still be close! We even saw a manatee in the canal.

Great view, easy check in, comfortable stay

Great experience, great host and accommodations. Hot tub wasn't working while we were there, but repair was delayed over the holiday week which was out of the hosts' control. Very communicative and responsive.

Nice, clean and quiet place. pool was nice. Nice view off the balcony is of the mangroves. Beach area is nice but pretty rocky once you get into the water.

Great place for a family. The pool and beach were ideal for kids and the little tiki bar was great for us. The surroundings were lush. We would stay here again.

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!

This was by far the cleanest rental we have stayed in. The inside of Kathryn's place was immaculate. The grounds in general were very clean and well kept. We saw multiple workers cleaning, doing landscape work, etc. during our visit. We spoke with several people we met who said their rentals were lacking certain things. That WAS NOT the case with Kathryn's place. She has honestly thought of everything from toiletries to coolers and pool toys. Ocean Point in general was amazing. The pool was HUGE. We loved having multiple places on site to grab a drink or food. Communication both during and leading up to our visit was very timely and informative. She was very accommodating. Overall we had a great experience and are already making plans to return again next year.