Family-friendly vacation rentals in Key Haven, Key West

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Key Haven, Key West family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Condo in Key West
4.82 out of 5 average rating, 45 reviews

Conch in the Treetops at The Beach

JeremyRating, 5 stars4 months ago
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.
Superhost
A charming porch features two white Adirondack chairs and a small table, surrounded by vibrant greenery. Light green shutters frame the door, which is centered on the white facade. The entrance is accessible via wooden steps leading to the welcoming front door.
Home in Key West
4.76 out of 5 average rating, 59 reviews

Historic Key West - Cigar House - Sleeps 4

LucasRating, 5 stars1 month ago
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.
Superhost
A panoramic view showcases the tranquil ocean, framed by palm trees and lush greenery. The scene captures a clear blue sky and the vibrant color of the water, with the outline of nearby buildings visible in the backdrop.
Condo in Key West
4.73 out of 5 average rating, 93 reviews

Top floor Ocean Views, Spacious 2 Bedroom Condo, V

JudyRating, 5 stars1 month ago
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!!
Superhost
A crystal-clear pool is surrounded by lush tropical palm trees, lounge chairs, and umbrellas. The calm water reflects a clear blue sky, creating a serene atmosphere. This outdoor space offers ample seating for relaxation, with the ocean visible in the background.
Townhouse in Key Colony Beach
4.77 out of 5 average rating, 31 reviews

Manatee Quay-2 Canal waterfront,access BEACH club

DanielleRating, 5 stars2 months ago
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!
Guest favorite
A spacious canal front home is displayed, featuring a large outdoor pool and spa area. The porch overlooks the water, surrounded by lush greenery. Lounge chairs line the pool deck, with a private dock accessible directly from the pool area.
Home in Marathon
4.98 out of 5 average rating, 91 reviews

4BR 3B, Heated Pool & Spa, 60' Dock

RobbieRating, 5 stars1 week ago
Amazing house. Beautiful surroundings. Plenty of room for 3 families and kids. Everything we needed.
Superhost
The outdoor area features a spacious pool with a spillover jacuzzi, surrounded by lush tropical landscaping. A thatched-roof tiki hut provides shaded seating, complemented by palm trees swaying gently in the breeze. The inviting space is designed for relaxation and enjoyment.
Home in Marathon
4.62 out of 5 average rating, 26 reviews

Sweet Retreat! 4 bedroom 2.5 Baths Sombrero Beach

LoriRating, 5 stars37 months ago
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!
Guest favorite
An Olympic size pool is highlighted in the image, surrounded by palm trees and lounge chairs. The building in the background offers several balconies, and a well-maintained garden area is visible, enhancing the outdoor setting next to the beach.
Condo in Key West
4.77 out of 5 average rating, 297 reviews

Affordable Beachfront Luxury Condo Sleeps 6

LynnRating, 5 stars1 week ago
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!
Superhost
A view of the ocean is captured from a balcony, showcasing the tranquil water under a clear sky. Lush greenery lines the shore, while a private dock is visible in the distance, providing access to the bay.
Home in Cudjoe Key
4.8 out of 5 average rating, 91 reviews

Palm Breezes! Room for Everyone on the Ocean.

RoseRating, 5 stars2 months ago
This place was a great get away. Perfect location between key west and marathon. Very quiet and private. Plenty of space

Family- and pet-friendly home rentals

Top guest favorite
Home in Marathon
4.89 out of 5 average rating, 37 reviews

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

LydiaRating, 5 stars8 months ago
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!
Superhost
A shaded porch area features four white Adirondack chairs with colorful designs. The view highlights a lush green lawn, palm trees, and a calm waterway with boats docked nearby, creating a serene outdoor setting.
Townhouse in Marathon
4.88 out of 5 average rating, 16 reviews

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

DanRating, 5 stars30 months ago
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.
Superhost
A well-maintained tennis court with a vibrant green playing surface and red surrounding area. Nearby, basketball hoops stand ready for use, and palm trees provide a tropical backdrop against a clear blue sky. The court is situated within a tranquil community.
Home in Cudjoe Key
4.61 out of 5 average rating, 161 reviews

Ocean Front Home in Great Location

SarahRating, 5 stars3 months ago
Was a very nice place. Loved sitting on the deck it was very peaceful and we went to the pool 1 day which was very nice. Easy about 25 minute ride into key west. Great location.
Guest favorite
Home in Marathon
5 out of 5 average rating, 13 reviews

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

ChristinaRating, 5 stars3 weeks ago
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.
Guest favorite
The two-story villa presents a light green exterior with multiple large windows, allowing natural light to enter. Elevated on stilts, ample space underneath offers shade, while the stairway leads to the main entrance. Architectural details emphasize a welcoming coastal style.
Villa in Marathon
4.88 out of 5 average rating, 57 reviews

New Paradise On Sombrero Beach

TonyaRating, 5 stars4 months ago
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.
Superhost
Home in Marathon
4.4 out of 5 average rating, 5 reviews

One Particular Harbor ~ Pool Home, 110' Dock

DianeRating, 5 stars2 weeks ago
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.
An outdoor tiki hut provides a shaded seating area with comfortable wicker furniture. Decorative cushions adorn the sofas, and a hammock hangs nearby. Lush greenery surrounds the space, offering a relaxing spot for gathering or unwinding.
Home in Marathon
4.96 out of 5 average rating, 159 reviews

Vida De Aqua - Water Life!

AntonyRating, 5 stars11 months ago
We came for our second stay at Judy’s lovely house. It’s very clean and very comfortable and in a great location. The tiki hut has very comfortable chairs and is a great place to unwind with a drink in the evening. Highly recommended!!
A light-filled living area features a comfortable couch and chair, complemented by a wooden coffee table. A small dining table with chairs is visible in the background. Wall-mounted artwork and two lamps add warmth to the space, with a large window providing natural light.
Home in Key Colony Beach
4.67 out of 5 average rating, 39 reviews

Lower Duplex. Canal & Dock. Pool Club included

LynnRating, 5 stars4 weeks ago
We love this place! close to the cabana club and beach. we are able to walk to the restaurant and bar in the evening. Loved the fire table in the yard we sat around it every evening. The area is so nice and quiet. We love everything about thud place. The host is very responsive to any question. This is our third time here and we will be coming back soon!

Family-friendly home rentals with a pool

Guest favorite
A modern bathroom features a glass shower and a white toilet. A stylish vanity with a blue vessel sink and multiple drawers is complemented by a large mirror with built-in lighting. Light green walls enhance the airy feel, while decorative art adds a touch of elegance.
Condo in Key West
4.96 out of 5 average rating, 76 reviews

Key West Paradise Poolside

AmyRating, 5 stars5 months ago
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!
Top guest favorite
Home in Key Colony Beach
5 out of 5 average rating, 44 reviews

Florida Keys Retreat / Completly remodeled

SeanRating, 5 stars1 day ago
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!
Home in Marathon
4.89 out of 5 average rating, 19 reviews

NEW LUXURY 4/3 SINGLE FAMILYw/HEATED P00L,BOATDOCK

BradleyRating, 5 stars8 months ago
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!
A sandy beachfront path leads toward the Atlantic Ocean, flanked by palms and tropical foliage. Seaside chairs and a thatched hut are visible, offering shaded seating. The water shimmers under clear blue skies, providing a serene setting for relaxation.
Condo in Marathon
4.7 out of 5 average rating, 69 reviews

Beach Hut: beach front, heated pool.

AaronRating, 5 stars11 months ago
THE best place to stay in Marathon. Private quiet beach and everything in the area. Stay here if you want to experience the Keys. I would recommend getting a rental or having a car.
Boat in Stock Island
4.67 out of 5 average rating, 3 reviews

Reduced Rate! Beautiful 46' Yacht in Resort!

JonRating, 5 stars3 months ago
Awesome experience! Great communication from booking through check in and during stay. Great boat in beautiful setting. Ton of amenities outside your door with downtown key west a quick shuttle away. Highest recommendation.
Guest favorite
Home in Marathon
5 out of 5 average rating, 19 reviews

Keys Waterfront Pool Home - Dock - Ocean - Kayaks

MeganRating, 5 stars4 weeks ago
We had a great stay at Mary and Jeff’s. The house was clean and comfortable and the kitchen was well stocked for cooking. We spent a lot of time relaxing by the pool, we fished off Key West, and we rented a boat for a day just down the street. If you’re looking to visit the Keys I definitely recommended their house for your stay.
A tranquil swimming pool is surrounded by lush tropical greenery, featuring tall palm trees and vibrant plants. Sun loungers line the pool area, inviting relaxation in a peaceful, secluded setting.
Condo in Key West
5 out of 5 average rating, 10 reviews

2 BR Condo Banyan Tree, Key West,FL

MaureenRating, 5 stars28 months ago
Place was nice and clean. We had a great time.
Guest favorite
Home in Key Colony Beach
4.95 out of 5 average rating, 152 reviews

Beautiful open plan remodeled home in Key Colony

BrennanRating, 5 stars5 months ago
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.

Quick stats about vacation rentals that are family-friendly in Key Haven, Key West

  • Total rentals

    80 properties

  • Nightly prices starting at

    ﺩ.ﺇ331 before taxes and fees

  • Total number of reviews

    900 reviews

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with a pool

    70 properties have a pool

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West
  6. Key Haven
  7. Family-friendly rentals