Kid-friendly holiday rentals in Key West

We absolutely loved our stay & already can't wait to visit again! We enjoyed the hot tub, kayaks, paddle board, corn hole, wildlife & napping in the chairs under the palms! We dined at the beautiful Marker 88 twice and thoroughly enjoyed it! We also had food and drinks delivered with no problem & had everything (pots, pans, toaster oven, etc) we needed to make breakfast! We primarily used the one bedroom house closer to the street, but loved having access to the house closer to the water for quick bathroom trips & cold water during corn hole and Sun bathing. Diane is so easy to work with and super helpful. Thank you for a beautiful stay!!

We had a fantastic stay at Villa Serendipity. Great location right off Duval Street within walking distance to everything. Private and secluded. The pool is small and shared with 12 units, but it was nice. The courtyard is welcoming and peaceful. Bed was very comfortable. Well appointed kitchen; having the ice machine was great! Hosts communicate well. Parking was tight but once we got a spot we didn’t move the car for the rest of the trip. Overall had a great time at this excellent spot in Key West!

Clean house, well decorated, great location and responsive hosts! It’s also a plus that they accept pets for a reasonable pet fee. Key Colony Beach is a great location and this is a lovely little home. Book with confidence!

Absolutely amazing place to stay! Dennis is amazing and had several great recommendations for us to eat and do! The dock out back was beautiful and we were even able to see manatees! The pool was a GREAT addition and my family wouldn’t have wanted to explore the Keys any other way! The neighbors are also friendly and great to talk to! Overall beautiful place! My family and I would stay again!

The house was clean and a great option for traveling as a large group. It was away from the bustle of Key West, but still easy to get around, and the restaurants nearby are delicious.

Loved every minute of our time here. Communication was excellent before during and after our stay and the house was superb. Highly recommended

I can’t say enough great things about this beach bungalow! From the moment we arrived, we were welcomed with warm hospitality and thoughtful touches that made our stay truly special. The bungalow itself is cozy, clean, and beautifully decorated with a laid-back coastal vibe—exactly what you want for a beach getaway. Whether you’re looking for a romantic escape, a solo retreat, or a peaceful base for beach adventures, this place is a gem. We left feeling refreshed and recharged, and we’re already dreaming of coming back!

Wonderful location, quiet community, and the property manager was amazing with communication. The home was absolutely beautiful, a great outdoor space, clean and cozy. Definitely would recommend!!

Very nice condo in key colony beach, affordable, great stay for a family. Clean rooms, nice pool, nice private beach area, will bring family down again.

Great place to stay for nightlife and shopping and very central location. Big room with lots of space and seating. Enjoyed that the bike and scooter rental were right down the street and Cuban coffee queen right down the stairs for a great coffee every am! Pleased with this unit and would definitely stay here again- do bring your own shampoo and conditioner and coffee just fyi. There was a small shampoo but no conditioner! Overall incredible place to stay! And the Host was so responsive and answered questions really fast!

Gorgeous spot! We stayed 3 nights and felt right at home in Laurie’s beautifully decorated apartment. It was very comfortable & we loved the pool and pool bar & the beach was stunning! I highly recommend this spot while visiting the area.

Great place with awesome location. Unfortunately I broke my ankle 2 days before our trip so my husband had to carry me on his back up the stairs to get in. I would definitely stay again but without the broken ankle next time!🤣

This airbnb was perfectly located and equipped with everything we needed. We loved it and would definitely stay again.

We stayed a week at the apartment. The place was spacious and clean. It was 6 of us and we didn t feel crowded at all. It has a full kitchen and we were able to cook some nights. The porch has an amazing view and the pool is plenty big to have thew kids happy. It is the perfect location if you like fishing and come with your boat (no problem with a 29' ). The Marina to launch is right there and the gas pump as well. Walking to Duval street takes about 10-15 minutes. It is a pretty walk. We ended up renting a golf cart because after a day of fishing, we were tired, but Uber is cheap and fast and bicycles can be rented too if walking is not what you want. I would stay again at Sloan s place !!

Magen was extremely kind, responsive and proactive in making sure we were informed about our upcoming stay and checked in with us as to how all was going all the way until check out and even after. Magen is a great host and we will be looking forward to our next stay.

This was our first family trip to the Keys and this location in Marathon was ideal! The condo was welcoming, beautiful and spacious for our family of 3. The balcony was our favorite place, which overlooked the pool and the seashore. The beach was lovely for shorter walks and just "being" with the ocean. Fun seashells & hermit crabs at low tide! Lots to do in the area -- definitely hoping to return next year. Mike was fantastic host & super helpful with questions.

Right next to Duval Street, easily walkable to major attractions, restaurants, bars.. Host was super responsive, friendly, and really worked with us on anything we needed.. Great place!

We enjoyed our stay! A little outside of the heart of Key West so it was very quiet. This place does have a unit above, luckily we were not bothered by any sort of upstairs noise. Would recommend!

Exceptional stay. Anchor Drop was a top Airbnb property in our book.,Would definitely look to return to both Key West and the property. Host was responsive, explicit, and helpful. Space was as described and very well appointed, clean, and comfortable. First time to Key West and was very satisfied with our accommodations, location, and area. Thank you!

Traci’s condo was great in every way! Everything was very clean and the view was amazing. We could enjoy watching the turquoise water and swaying palm trees from almost every room – both bedrooms, living room, kitchen, dining area, or relaxing on the large balcony. Some of the furniture is different in the photos, but my group agrees it is even better now than what you see. Having our own parking space in the garage was much appreciated, too. Traci responded quickly; clear check-in instructions. We would definitely stay here again.

Kimberly’s condo was the perfect home base for exploring the upper keys. We enjoyed the views, the well equipped kitchen, and the pool!

This listing was everything and more! The space was very clean, and provided all of the necessary amenities. As far as location…top tier. All the major attractions and beaches were a short 15 minute drive. Chris was responsive when I reached out. Truly a gem, and I would recommend this space again and again.

Had a nice time at Jennifer’s place! The space was very well cleaned and looked just like the pics. There must have been some construction going on because it was a bit noisy. Otherwise, it was great!

Absolutely perfect for a honeymoon getaway, quiet perfect amount of space for us, the set up was great with 2 bathrooms and a huge walkin closet, the couches were super comfy, the TV was big enough to see from across the room, we enjoyed everything about it. Got to meet some of the neighbors and they were all very welcoming and enjoyed talking to them. Scott had some great local recommendations and we enjoyed everything.