Family-friendly holiday rentals in Key West

We rented Ryan’s home during the week of our wedding in Key West — much more reasonably priced than KW, and only about an hour away. Home is clean, modern, well appointed. Heated pool and hot tub were a big hit with our family, especially kids (worth the extra charge). The pool was dirty when we arrived so when Ryan saw pics he deemed it unacceptable and sent a cleaner out to address it right away — he had a delicious key lime pie delivered for the inconvenience, which was a sweet gesture. It was good to have 2 wings to separate the bedrooms (main plus queen both with private baths on one end). We had 10 people in the home (including 4 kids) and had ample space. Helpful to have chairs and cooler for beach (umbrella didn’t hold up to windy day) — Sombrero beach while crowded was nice. Lighting outside to enjoy outdoors at night could be better, but awning to shade the chairs from sun during day is a great feature. Bring a Bluetooth speaker for music. We’d come back! Thanks, Ryan!

Great space in the condo, love the pool and amenities area. All simple and easy. The parking was great. Felt really safe. Wonderful to be able to walk toSmathers Beach.

What a wonderful stay on Duck Key! Very convenient to various points on the Keys. The house was spacious, clean, comfortable, and beautifully situated.

Ed was very responsive to my inquiries. The condo was exactly as described. The unit was clean and well stocked. It was close to the beach and a short uber drive to the old key west area.

We had a great time at this resort during spring break. The listing is as described with helpful suggestions for activities and restaurants. There was always music playing at the pool, contributing to a festive atmosphere. The rooms were clean and well stocked. Largo was a communicative and helpful host.

Great spot in the resort property . Courtyard outback was tranquil… One young buck who was cleaning his boat on Sat had his music waaaay to loud but once he finished it was quiet again. Bed comfortable, kitchen well stocked. We stayed 2 days on our way down to Key West to enjoy Marathon and Turtle hospital. It was nice also that she allowed less than 3 day rentals :)

This house was just what we ordered for a perfect Keys vacation. It was clean, comfortable, and ideally located in the middle of the Keys for day trips east and west. The Cabana Club was also a bonus if you feel like some pool or beach time, but get there early.. Brad was extremely responsive to all inquiries. The best thing about this house is the view. We spent hours just sitting on the covered porch and sunny decks enjoying the water views. You can't get any closer to the water and there is plenty of furniture for all your needs. We saw dolphins every day, as well as rays and manatees. We liked fishing from the docks, too. Great experience!

The place is well maintained and equipped! Thought of the little things to make your stay enjoyable. I would highly recommend staying here and if we ever make it back would stay there again.

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!

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.

Overall we enjoyed our time here. It can be hard to find from the road but has a rustic charm to it. Enjoyed kayaking and time in the tiki hut by the water.

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 stayed here with friends with a total of 10 people, 4 adults and 6 kids. There was plenty of room for everyone never felt crowded. We all had a great time!

A very affordable, adorable RV right near shopping in Key Largo. I rented for my son and his fiance and 4 month old baby to escape the aftermath of Hurricane Milton up in Sarasota county. They enjoyed the privacy and the Publix nearby. They also kept busy doing the various puzzles that were available for use, being that it was an unplanned vacation with little money to enjoy The Keys. I will rent again when other family and friends come down.

Great place. A small kitchen if your wanting to cook a lot, no dishwasher. Loved having our boat right out back. Close to pretty much every and anything you'd like to do. The cost was very affordable compared to other places we've rented but was definitely a downgrade from those other places, the money was right for what it is. Older beds were a lil uncomfortable for our two week stay but not unsleepable. Couch in living room could use a shampooing, we purchased a blanket to have a cover on it. Host was attentive and friendly. Would recommend, definitely had an enjoyable stay for the most part. Couldn't ask for a better location either.

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)!

It makes such a difference when it's someone's own vacation home. Everything from kitchen to furniture to systems worked great and we were able to feel at home from the moment of arrival. Comms with Camille was easy both by email and text and she provided a detailed set of instructions for everything. Bed configurations were as described. Sofa beds were better than expected and plenty of bed clothes were provided. Dive shops, restaurants, supermarkets all within short drive. There is a beautiful pier on site for watching the sun rise or set. A little pricey compared to other properties but I would go back because of the quality of the property and ease of staying there.

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.

Best location in Marathon! We just loved this home. It was close to stores, yet felt very private being on a dead end road and having nature across the canal. The outdoor area was perfect! The screened in porch was needed for the no see em bugs this time of year. Pool was a little oasis. Fishing area was great. Plenty of room if you have a boat but we opted for Ana banana charters (which I would recommend). Kitchen was well stocked with everything we needed to cook. House seemed bigger to me than pictures. We would love to come back soon!

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.

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.

We had a wonderful week. House was beautiful and pool was so relaxing. Loved the location. Ever was friendly and responsive for all questions we had. We would love to go back. 😊

We really enjoyed our stay at Lucia’s place! The short walk to the beach around the lagoon was beautiful. Two pools close by gave lots of options for our week long stay. The binder of restaurant suggestions, activity pamphlets and other good to know info was very helpful! Thank you for that! We will be back again!

Went to Cynthia's place 1/18-1/21. It was better than the pictures. The Kawama community, the lagoon and Key Largo are beautiful. First time visiting Key Largo and there's much to do.,,fishing, snorkeling, biking, and visit John Pennekamp Coral Reef State Park. I went with my three sons for a long weekend for fishing and went to Key West. The lagoon is few feet from the patio to enjoy a swim. My boys loved it. Cindy kept in touch with me to see if everything was good. I had a great time and her place is is neat, clean and meticulously maintained. Go and enjoy!