Family-friendly vacation rentals in Key West

Although the place wasn’t ready when we arrived, Ryan was a great communicator! He addressed every issue we had (which were NOT within his control) and responded in a timely manner. He offered a fair solution and allowed us to sit back, relax and enjoy paradise! I’d highly recommend and hope to be back sometime soon!

Amazing house. Beautiful surroundings. Plenty of room for 3 families and kids. Everything we needed.

You won’t find a better set up than this with family. Playground, beach, pool , sidewalks for walking everywhere, and great kayaking area as well. And the owner makes sure his guests have all they need.

This place had everything we needed for a relaxing family vacation prior to the crazy Holiday season. we only had 6 people but it would easily accommodate more. Monica was responsive to any questions or concerns. The location was perfect. Easy access to sombrero Beach and Marathon amenities: bars, restaurants, and activities. we were able to experience a turtle release on Sombrero Beach from The Turtle Hospital. Highly recommend renting from Monica again and on Marathon Beach.

Beautiful place. Nice neighborhood. Would stay again. 10/10 recommend.

The Grouper house was fabulous. I stayed there with my wife and kids for a week. Everything about this place was top notch. From booking to check in and check out. Her staff is nothing short of superb. Sean makes sure every need or question is answered promptly. The best place I have ever stayed. Highly recommend.

Great spot in the resort property . Courtyard outback was tranquil… One young buck who was cleaning his boat on Sat had his music waaaay to loud but once he finished it was quiet again. Bed comfortable, kitchen well stocked. We stayed 2 days on our way down to Key West to enjoy Marathon and Turtle hospital. It was nice also that she allowed less than 3 day rentals :)

Excellent place to get relaxed Definitely we may come back

The stay here was great! Very clean, great location/on property amenities, and quick communication. Would definitely recommend to a friend!

The Cigar House is great - we enjoyed the easy walkable access to all the amenities in the neighborhood, including bars, restaurants and the Zach Taylor park. The location is really the key here. The grounds are beautiful and the pool/hot tub were nice features. Would definitely stay again.

Our stay at this home was absolutely perfect! The location couldn’t have been better—peaceful, relaxing, and right on the water. We spent so much time unwinding on the dock, soaking in the beautiful views and enjoying the gentle ocean breeze. The Marathon area was a fantastic place to explore, offering everything we needed for an unforgettable getaway. We loved being close to state parks for hiking and wildlife spotting, as well as having access to amazing restaurants serving fresh seafood. Bike rentals were nearby, making it easy to explore the area at a leisurely pace. If you’re looking for the perfect blend of relaxation and adventure, this is the place to be!

Great place close to everything!! We decided against renting a car and I am so glad because everything was walkable. The AC worked great which we very much appreciated. The cuban restaurant downstairs and the CVS right across the street really made everything super convenient. We would definitely stay here again!

My husband and I thoroughly enjoyed our stay here and have already rebooked. Newly remodeled, private and walkable. Secure, pristine community with lovely grounds. Host was very helpful and prompt in responding.

Absolutely fantastic unit and location, and the communication and service from Last Key was white glove. Top notch. We will be back.

We came for our second stay at Judy’s lovely house. It’s very clean and very comfortable and in a great location. The tiki hut has very comfortable chairs and is a great place to unwind with a drink in the evening. Highly recommended!!

we had a great time in thr apartment of Largo. He gave us very precise information for the arrival, and various recommendations in the area. The apartment was very clean and the kitchen well equipped. The pool area nearby was also great! I would definitely recommend this apartment!

Our family of 5 loved our time in Islamorada. The community was beautiful and quiet. It was definitely mostly retired couples but everyone was friendly with our young kids. The condo was bigger than the pictures made it seem- we had more than enough space. Everything was clean and we had everything we needed.

Andrew’s place was very clean, and he is a very hospitable host! We thoroughly enjoyed our stay, and will be reaching out to him when we come back to the Keys again! I lived in Marathon FL for a long time, and know the keys well. It is rare to find a host as good as Andrew down there! I HIGHLY recommend staying at his place if you’re considering visiting. Great, private Yacht club with a boat ramp/marina, hidden right off the main drag of Key largo.

The photos and amenities were exactly as described. The home was comfortable and Glenn is amazingly responsive. His air blasts cold, the pool was heated and the grounds were nice.

This house was a perfect spot for my partner and I and Cooper our pup. swam in the pool, sat in jacuzzi, paddle boarded ,kayaked, road the bikes, ect. we brought our boat down but unfortunately had a few issues with it so wasn't able to go out fishing as much as we'd liked. but there was plenty to do at and around this beautiful place. would definitely come back in the future:))

My friend and I stayed at this lovely house in a well maintained community. The house is clean and very nice. The owner was very responsive. We had no issues during our week stay. The community pool was fantastic. We grilled a few nights and took advantage of the great restaurants within 10 minutes away. Highly recommend unit and location.

We had a fantastic stay here during our week in Islamorada. The house was incredibly clean, uncluttered, and had a nice feel. The road noise was pretty much constant, which we were prepared for ahead of time based on other reviews. But noise makers were provided and helped a bit. There were full sized soaps in the kitchen/bathrooms. There were plenty of cleaning supplies in the kitchen including garbage bags, Clorox wipes, and dishwasher detergent. Beach/pool towels were also provided. All of these amenities make it easier when traveling by air. The property had paddle boards and kayaks for use on a first come first serve basis. All 5 of us, my hubby, our three girls ages 13, 19, and 21 had a fantastic time paddling around nearby. Watching the sunset was particularly lovely on the water. There were some fantastic restaurants nearby that were walkable and within a 5-10 minute drive. If we were to come back to the area, we would definitely consider staying here again. Thank you!!

Great stay and location. Chris was super helpful with check in and had great communication

Claire had an emergency which caused her to forget to contact house cleaning but she was awesome to work with and went over and above to make it right when we told her of the problem. You won’t find a more beautiful private place to stay. Location is as good as it gets. Claire was a great host and we really appreciated it.