Family-friendly holiday rentals in Cudjoe Key

Our unit was perfect for what we needed. It was stocked with everything we couldn’t bring with us in travel (chairs, towels, coolers, etc). The condo amenities were also everything we needed and the pool/on site beach were amazing. Our host was very proactive in communicating check-in details and offering support/recommendations whenever we needed it.

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.

This was our first time in Key West. We wanted to stay a little tucked away from the downtown bustle. The complex is beautiful with great amenities. And it’s close enough to shopping, restaurants and bars! We definitely plan on booking the same place in the future!!

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

Everything was perfect for our stay at Airbnb, the pool felt amazing, the views were stunning, and the Uber drivers were incredibly fast. Even the locals agree that this is the best place to stay in Key West, and I couldn't agree more - I'll definitely be back. Our host, Traci, was absolutely top-notch!

nice and clean condo with private parking. great host.

Beautiful views, well appointed condo, great amenities and location is very convenient.

This place was a great get away. Perfect location between key west and marathon. Very quiet and private. Plenty of space

Highly recommend this location and townhome. Everything was really clean and the kitchen was well stocked. Our children really enjoyed the huge pool and the area attractions. Our favorite spots to send time were Sombrero Beach and Sandspur Beach at Bahia Honda State Park. We rented a boat for a few days and went out to the Sombrero Reef and the sandbar. So much fun! We are definitely coming back to stay at this home again.

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!

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!

The house was fantastic; it was clean and very comfortable. My family and I had the best time and felt right at home… just more relaxed! My kids especially liked the pool and the beautiful outdoor space. The house was stocked with all the basics to get us started for our week, the neighborhood was quiet and safe, and the proximity to the beach was unmatched.

Fish Camp was spotless and the owners and property management were very communicative leading up to our trip and once we arrived. No major issues - and if we reached out they responded right away. Beach chairs would have been a great addition for our stay.

We had a great time, and the place was perfect for what we were looking for. The dock had room for my 25' center console and my two sons-in-laws smaller inshore boat and flats boat. Plus being able to keep the trailers on property was huge for us. As far as the house, it was very nice inside and the layout worked out nice for the 8 of us. The pool was perfect and was positioned in such a way which allowed direct sunlight through the whole day for most of the pool and had some shade on one side for those who wanted to get out of the sun for a while (at least during this time of year). It had two paddle boards and two kayaks which we used every day. The kitchen had everything we 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.

The RV lot was well landscaped making the space feel tropical. Access to bath and laundry facility were just a few steps from the lot.

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.

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:))

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!!

We had a wonderful stay for our annual family fishing trip. Lots of privacy with the corner lot which is a premium in Marathon. Great location and close to everything you need for your trip.

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)!

Rolando was an excellent host! We thoroughly enjoyed our time at his place. The location was exactly what we were looking for as it was central in the keys and close to everything. We did run into a problem while there, but Rolando was extremely responsive and helpful and had the issue solved literally the very next day. All in all, it was an excellent place to stay.

Beautiful place, exactly as pictured, for our family of six. We LOVED the pool and spa! The porch space was well used with lovely furniture overlooking the pool. Great location for restaurants and activities. The landscaping and grounds are beautifully maintained. Very peaceful and private during our stay.

This house was absolutely amazing! Our family had the best week here. The outside area was so nice and lots of room. We all enjoyed the pool. I loved to sit on the swing every morning and evening. The house was perfect, had everything we needed for our family of 6. It was walking distance to the cabana club that we very much enjoyed also. Lots of food options within a 15 min drive. We would absolutely love to come back and stay.