Family-friendly holiday 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
Apartment 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 favourite
Home in Marathon
4.98 out of 5 average rating, 91 reviews

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

RobbieRating, 5 stars2 weeks 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 favourite
Apartment in Key West
4.78 out of 5 average rating, 298 reviews

Affordable Beachfront Luxury Condo Sleeps 6

LynnRating, 5 stars2 weeks 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
Home in Cudjoe Key
4.8 out of 5 average rating, 92 reviews

Palm Breezes! Room for Everyone on the Ocean.

GerritRating, 5 stars2 weeks ago
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!!
Guest favourite
Home in Key West
4.82 out of 5 average rating, 93 reviews

Historic Key West - Conch House - Sleeps 5

JohnRating, 5 stars3 weeks ago
We enjoyed our stay. The location of property was perfect to experiencing Key West. The pool and courtyard area was very private
Superhost
Cottage in Key West
4.73 out of 5 average rating, 33 reviews

Darling of Duval at Old Town

JoeRating, 5 stars2 months ago
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.

Family- and pet-friendly home rentals

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
4.62 out of 5 average rating, 162 reviews

Ocean Front Home in Great Location

Delanie FaithRating, 5 stars2 weeks ago
Amazing location and super clean. Beds were so comfy!!
Home in Marathon
4.9 out of 5 average rating, 20 reviews

Villa Casa Cayo

AmyRating, 5 stars4 months ago
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.
Guest favourite
Home in Marathon
5 out of 5 average rating, 13 reviews

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

ChristinaRating, 5 stars1 month 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.
Superhost
Home in Marathon
4.63 out of 5 average rating, 8 reviews

Pier Pressure~ Waterfront Pool Home, 100' Dock

RobertRating, 5 stars10 months ago
We had a great time, and the place was perfect for what we were looking for. The dock had room for my 25' center console and my two sons-in-laws smaller inshore boat and flats boat. Plus being able to keep the trailers on property was huge for us. As far as the house, it was very nice inside and the layout worked out nice for the 8 of us. The pool was perfect and was positioned in such a way which allowed direct sunlight through the whole day for most of the pool and had some shade on one side for those who wanted to get out of the sun for a while (at least during this time of year). It had two paddle boards and two kayaks which we used every day. The kitchen had everything we need.
Guest favourite
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.
Home in Marathon
4.96 out of 5 average rating, 160 reviews

Vida De Aqua - Water Life!

HeathRating, 5 stars11 months ago
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.

Family-friendly home rentals with a pool

Guest favourite
Apartment 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 favourite
Home in Key Colony Beach
5 out of 5 average rating, 44 reviews

Florida Keys Retreat / Completly remodeled

SeanRating, 5 stars1 week 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 stars9 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!
Apartment in Marathon
4.7 out of 5 average rating, 70 reviews

Beach Hut: beach front, heated pool.

StephanieRating, 5 stars2 weeks ago
Beautiful location right on the water. Great views. Peaceful location
Guest favourite
Home in Key West
4.96 out of 5 average rating, 254 reviews

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

LoganRating, 5 stars2 weeks ago
Wonderful stay, Naomi was a helpful host who responded quickly while also being flexible in order to make our stay great! Wonderful location as everything we wanted such as Duval street was in walking distance. The room itself was great! Hot tub was a nice bonus
Guest favourite
Home in Marathon
5 out of 5 average rating, 20 reviews

Keys Waterfront Pool Home - Dock - Ocean - Kayaks

MichaelRating, 5 stars1 week ago
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!
Apartment 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 favourite
Home in Key Colony Beach
4.95 out of 5 average rating, 153 reviews

Beautiful open plan remodeled home in Key Colony

MargaretRating, 5 stars2 weeks ago
Wonderful welcoming beautiful place to stay! Close to excellent restaurants and several beaches. Has outstanding large screened in porch on the canal with comfortable seating. Access to club house with large sparkling pool and beach 2 min. drive. Excellent drinks. Highly recommend!!!

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