Family-friendly holiday rentals in Cudjoe Key

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!!

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!

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

Beautiful home that comfortably held our 6 person family of adults. Absolutely loved the pool, spa, and outdoor seating. Really nice kitchen and bathrooms. We used Marathon as home base and drove to Key Largo, Key West, etc. Always nice to return to the house and pool to relax!

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!

10 out of 10 stay. Beautiful, serene property where we often felt we had the mangrove and key to ourselves. Several days were spent on a recurring rotation of kayaking, pool, hot tub, repeat. Perfect distance from Key West for adventuring there, but plenty on Cudjoe Key and Big Pine if you don't want to venture to the hustle and bustle. Sincerely hope to return!!

What a great place to stay for a Key West trip! Perfect location, lots to do, super short walk to Duval St. Very easy check in, and Last Key were easily available for questions.

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.

Amazing location and super clean. Beds were so comfy!!

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.

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.

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.

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.

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:))

Beautiful location right on the water. Great views. Peaceful location

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 really enjoyed our stay on the boat and also our two hour sunset cruise. All the staff we interacted with were friendly, knowledgeable and helpful. Great location and very fun experience.

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)!