
Family-friendly holiday rentals in Key West
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Key West
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
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Popular amenities for Key West family-friendly rentals
Family-friendly home rentals with a hot tub

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish
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!

4BR 3B, Heated Pool & Spa, 60' Dock
Amazing house. Beautiful surroundings. Plenty of room for 3 families and kids. Everything we needed.

Sweet Retreat! 4 bedroom 2.5 Baths Sombrero Beach
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!

Affordable Beachfront Luxury Condo Sleeps 6
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!

EYW Getaway
Edward's place was great! we really enjoyed the home like vibe. It had everything we needed during the stay. The sunset view from the balcony was beautiful.

Plunge Pool Villa on Blue Water Lagoon
Loved this little place to get away for a relaxing weekend, very cozy and comfortable. Looking forward to coming back soon.

Family Key Largo Townhome for Fun Sun & Relaxation
Our group of 8 stayed Feb 2025. The home is nicely decorated, clean, and Jose supplied a starter set of toiletries for the shower, hand soap, toilet paper, paper towels, dishwashing liquid, dishwasher pods, some coffee pods, and spices for cooking. They supplied large beach towels for the pool, a small cooler, and noodles. The oasis pool and hot tub were awesome. Don’t miss the second pool by the marina that is heated and a hot tub grotto which was perfect in the evenings. 2 pools, 2 hot tubs, you just can’t beat it! This townhome is located near many restaurants and fun places for activities. You enter the home from the first floor but second floor is the main living area with full kitchen, living room, and nice balcony. Two bedrooms are on the third floor so lots of stairs but worth the trip. First floor has a private king bedroom with a pull out couch in the living area and a small kitchen. Laundry room is in a storage area outside next to the front door. We loved our stay and Jose!

Casablanca Too ~Chicly updated home with hot tub
The home is lovely. Updated kitchen, comfortable bed, outdoor grill and private parking spot were all pluses! The communication with the host could not have been any better. I look forward to returning one day soon!
Family- and pet-friendly home rentals

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish
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!

Waterfront luxury Villa (14) with sunset views and boat slip
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.

Manatee Quay-2 Canal waterfront,access BEACH club
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!

Cottage w/ Private Yard, Free Kayaks, Boats, Etc
We really enjoyed our stay with Key Lime sailing club! We especially appreciated the easy access to water activities and created life long memories kayaking in the beautiful surroundings. The hosts are kind, helpful and made our stay more memorable!

Fish Camp, Fun, Keysy Oasis, with Tiki, pool, dock
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.

New Paradise On Sombrero Beach
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.

Modern 2 Bedroom/2 Baths RV. Pool, Beach, Marina
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.

Bring Your Own RV! Our Lot Your RV B6 No Tents
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.
Family-friendly home rentals with a pool

Historic Key West - Cigar House - Sleeps 4
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.

Waterfront, dock, easy ocean access, heated pool!
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:))

Angler's Reef Oceanfront
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.

Villa Casa Cayo
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.

Bayside Townhome in Islamorada with Boat Slip
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.

Your island home away from home!
Bonita taca al lado del mar para pasar unas buenas vacaciones con la familia

Vida De Aqua - Water Life!
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.

Kawama Suntastic @ Key Largo
My family and I had an absolutely wonderful stay. We enjoyed swimming and powder boarding in the lagoon, feeding the fish, fishing off the point, relaxing poolside, and enjoying our time in Key Largo. Check-in was super easy and the owner, Cindy, was an absolute delight. Very smooth and easy, five stars, highly recommend, especially for children or anyone looking for a relaxing time.
Quick stats about holiday rentals that are family-friendly in Key West
Total rentals
1.4K properties
Nightly prices starting at
$109 AUD before taxes and fees
Total number of reviews
29K reviews
Pet-friendly rentals
420 properties allow pets
Rentals with a pool
1.1K properties have a pool
Rentals with dedicated workspaces
770 properties have a dedicated workspace
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