Family-friendly vacation rentals in Key West

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.

Beautiful place to stay, fully equipped and within walking distance to everything.

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.

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.

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!!

nice and clean condo with private parking. great host.

My daughters and I came from 3 different locales to spend a few days together at Henry's condo. We were very comfortable. The condo is stocked with kitchen utensils, beach towels and chairs, tvs, and a sound system. It was a bit chilly for the pool, but we enjoyed the community's hot tub and landscaped community area. Smathers Beach is a short walk away. Higgs Beach is also walkable and has plenty of parking. I wanted to try the snorkeling trail at Higgs, but it was a bit chilly for me. Still, February in Key West was a welcome relief from the 20 degree weather and snow I left behind! There was a lot of paperwork for an Airbnb ahead of arrival, but everything went great. Henry was always available, responsive, and helpful. We had a terrific reunion and enjoyed Key West.

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.

I stayed at the Truman Annex last year for the boat races and loved the location. I decided to rent from Wally this year due to his condo was more open and also had a 2nd bath! He was very responsive when I texted him, the house was very clean and everything was perfect, I highly recommend!

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!!

This home was just what my family needed for our vacation! We all loved relaxing in the outdoor living room surrounded by greenery. We also enjoyed swimming in the pool and kayaking through the canals and Boot Key. We made most of our meals due to dietary restrictions, and the kitchen here was adequate. The location in Marathon is excellent! It was just a 5-minute walk to Sombrero Beach, so we never had to worry about parking. We could easily drive to all the activities we wanted to do in the area, too.

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

The view is beautifully tropical with the ocean water alternating turquoise blues! The white sand beach, palm trees and sparkling pool added to the ambience. The condo had everything we needed, beach towels, umbrella and beach chairs were a plus. There is a high school next door so you can expect high school activities. As it was our first experience in the keys, the location worked well for us. We could go back and forth across all the keys and experience what they had to offer.

Beautiful place to stay with family and friends. The location is great. Everything was as described in the listing. We really enjoyed our time there.

It was an unforgettable week in Maria and Johnny's house. The house was very clean and beautifully furnished. Each of our three children had their own room in which they felt very comfortable. Our bedroom had a large terrace where my wife could do yoga in the morning sun. The kitchen and living room were really well epuiped and terrace with the hot tub were just right for a relaxing family holiday. Nothing was missing. Communication with Johnny was easy and quick. He gave us great ideas for activities and restaurants in the area. Thank you for that. We can highly recommend Maria and Johnny's accommodation!

My family and I stayed here for the whole month of January and, despite the weird weather, we had a great time! Naylen's place was perfect for us and she was very responsive to any minor issues we had. We loved the backyard setup with the pool, fish cleaning station, ice machine, dock, outdoor grill and surround sound. Having access to the neighborhood's private boat ramp was a huge plus! The landscaping is done very well to make the backyard feel very private. The house is within walking distance to a cute restaurant called Crooked Palm and close driving distance to a bunch of other really good restaurants. It's also close to Founder's Park which we had free access to. Our kids enjoyed the park's beach and playground. Overall, Naylen's place is a great setup and we would highly recommend.

The Airbnb had a great location. My husband enjoyed the local fishing, which was a block away. The Airbnb was clean and very comfortable. We also enjoyed the taco truck and Tiki bar located on the premises. The most important thing was that we could bring our dog Chloe and felt comfortable and safe. We will come back again to the cottage.

The space and the location were absolutely amazing. I could not have asked for a better vacation home. Home is exactly as described. Home and community amenities are exactly as describe and PERFECT. The beach and pool were great. The provided kayaks/SUPs and fishing gear were a total hit. The space is well thought out, decorations perfect, every home comfort provided. Jennifer was extremely helpful with recommendations. We actually used several of her recs for sandbar visits, backcountry fishing guide, and restaurants. She was super helpful, communicated great, and we had the very best vacation ever. The host made the vacation just as memorable as the house itself. Jennifer is an excellent host, and I'd absolutely stay at one of her properties again. Hope to be back in Islamorada soon!

Beautiful view and clean home. Watch gorgeous sunrises right from the screened in porch or out on the dock. Great local restaurants close. We highly recommend The No Name Pub (amazing pizza, and make sure you bring a dollar for their wall). The Bent Prop was another favorite and was only about half a mile away. Breakfast recommendation is to go to Key West to Blue Heaven (try the banana bread)!

Just what we needed for winter break , loved having coffee in the morning on the canal, hammock very relaxing, liked the open living space.