Family-friendly holiday rentals in Cudjoe Key

The experience was so memorable! Just the R&R our family needed!

Perfect for our family of 5. Great outdoor area at the house for fishing and relaxing. The layout was great for us because of the separation from the master to the kitchen/living room…our baby could sleep and we didn’t have to worry about making noise and waking up the baby. KCB is in a great central location for exploring the Keys. We were also pleasantly surprised at the quality of restaurant’s nearby. The Cabana Club was crowded and has a small beach. Drinks there were good. I have nothing overly negative to say, other than that I wouldn’t look to stay in KCB or this property if you just want to hang at the pool and beach all day. But it was fine for a few easy afternoons between other activities in the area. We highly recommend and would stay again!

Windswept Palms was beautiful and we enjoyed the setup. The pool and beach were very clean and quiet. The views are absolutely amazing!! We were able to walk in the ocean one day and it was so clean and clear. Victor, the host, was very nice and helpful!! Beds were comfy and so was the couch.

Plenty of room for all the family and their families. We enjoyed all the backyard amenities with pool, kyacks, boat dockage and fish cleaning station. There was sufficient seating for everyone and a great area to hangout. The only things we struggled with was TVs didn’t work properly in some of the rooms, no washcloths or kitchen towels available. With that being said, we will definitely consider renting Ryan’s place again in the future!

Our stay in Marathon couldn’t have gone any better! I traveled with my three 20-something sons and their wives/significant others. The layout of Gerardo’s home was perfect for our needs. We had plenty of room, places to enjoy together, and space where everyone could find some peace and quiet. The location was ideal. We were within an easy driving distance of all excursions and restaurants and could even walk to Island Fish Company, which was one of our favorites. Gerardo was extremely responsive. He checked in prior to our arrival and touched base a couple of times to make sure there was nothing we needed. An excellent home I recommend to others with no hesitation!!

Fantastic place for a home base while the beautiful keys. Close enough to key west for an upbeat day, very quiet in the evening. If anything, I’d say I was expecting less from the description and was very surprised at how nice this place is. I would stay here again in a heartbeat!

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.

We had a great stay! The place was clean, comfortable, and had everything we needed. The location was perfect, and communication with the host was smooth and easy. Would definitely stay here again, highly recommended!

It is a great place just a little tight getting the camper in The neighbors are all very friendly and helpful

We booked this home last minute and now have our go-to vacation spot in Marathon! Alida is a friendly host with great communication. The home is very clean. Beds are very comfortable. Kitchen is well stocked with pots, pans, etc. The kayaks and paddle board made our vacation even more special! The steet is very quiet and peaceful. The setting in the back yard is very private, as is the long dock. We had a 23' rental boat for our stay. The view is amazing and the sunsets are a special treat each evening. I very much appreciated the ample, comfortable seating everywhere - inside and outside of the home. Thank you Alida. We made great family memories here!

Great place and location. Close to lots of restaurants. Pool was really nice! Kitchen was fully stocked and nice that they provide paper towels/toilet paper/dishwasher detergent/etc. to get you started. Had a nice bottle of champagne waiting for us upon arrival as well.

The house was well equipped with all of the essentials. We had 8 adults and plenty of room. We did have to wash towels a few times, and buy more laundry soap, but the washer and dryer were conveniently located on the main level. The pool was smaller than what the pictures showed, but it perfectly suited our needs. All members of our party viewed the listing before we booked it and none of us realized it was a twin home. However, there is tons of privacy and the only times we noticed we had neighbors was when the shared dock was used. We had to buy a cooler (for poolside and the beach) and beach chairs. There were some pool floaters left behind, from previous guests that we used. The interior of the home is beautiful, with high ceilings and comfortable furniture. This is in a great location - close to grocery stores, restaurants and Sombrero beach! Monica was great to work with!

Our group of six adults loved our stay at One Particular Harbor! The property was beautiful and spacious! The pictures couldn’t do it justice. Our hosts were very helpful and attentive! We would definitely stay there again.

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.

Had a great stay here! The hosts were very kind and attentive and even left surprises for our daughters who graduated. Nice, comfy and clean home and we would definitely recommend staying here!

Jack and Susan are wonderful hosts! Their home is beautiful. It felt like home and the small, private beach area was so peaceful. Susan gave great recommendations on places to eat and things to do and was always responsive to all questions I had. Would definitely stay again!

We had never been to the Keys before and were not sure where to stay. Islamorada ended up being an excellent choice. There was a great variety of activities nearby, and within a 30-45 minute drive there were even more unique places to visit. The private community where Gina's house is located feels like a mini-resort that The Mouse would be proud of. The community was clean, the staff were extremely friendly, and the other people we met were all gracious. Gina's house was well located - close to the entrance and a 1-minute walk to the pool. The house was super clean, comfortable, and the few things we had questions about were immediately dealt with by Gina. We're considering another trip to the Keys and would not hesitate to stay here again or recommend it to another group.

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!

It was an awesome place! Beautiful, clean, and cozy! You can pull your boat right up to the dock! easy access threw the canal to the ocean and a couple of restraunts! pools nice! plenty of room for a big family! All of your amenities are nearby! Grocery store, restraunts, bars if your into that, gift shops and more!

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:))

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.

We had an unforgettable stay at Mary’s place! The house was spotless, cozy, and truly felt like a home away from home. We spent most of our time relaxing by the pool—it was so peaceful and quiet, the perfect setting for some much-needed downtime. The location was incredibly convenient, with grocery stores and great restaurants just minutes away. One of the most special moments of our trip happened here—we got engaged! I honestly couldn't have imagined a better place to celebrate such an important moment in our lives. If I had to suggest anything, the house could get a bit warm at times with the thermostat set at 72, but it wasn’t a deal breaker at all. Mary was amazing—super responsive, helpful, and kind. We would absolutely come back. Thank you for such a memorable experience!

Place was nice and clean. We had a great time.

We absolutely loved Jennifer’s home! The house was so clean and had everything we needed included towels, kid’s toys and even baby gates for the stairs. The pool was so perfect and we had a blast swimming every day. We highly recommend staying at this beautiful property and will be visiting again!