Family-friendly vacation rentals in Sunset Key

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Sunset Key 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
Condo in Key West
4.73 out of 5 average rating, 94 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
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
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
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
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
Condo in Key West
4.68 out of 5 average rating, 201 reviews

Sunrise Suites Resort, Key West FL U #408 2bdr2bth

LeonRating, 5 stars2 weeks ago
nice and clean condo with private parking. great host.
Superhost
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
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
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
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.
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!!

Family-friendly home rentals with a pool

Guest favorite
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 stars2 days 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!
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 stars1 month 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.
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.

Destinations to explore

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  4. Monroe County
  5. Key West
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  7. Family-friendly rentals