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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

Top Guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 45 reviews

Florida Keys Retreat / Completly remodeled

SeanRating, 5 stars1 month 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!
Guest favourite
Home in Marathon
4.98 out of 5 average rating, 92 reviews

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

MondeRating, 5 stars2 weeks ago
Our stay in Marathon couldn’t have gone any better! I traveled with my three 20-something sons and their wives/significant others. The layout of Gerardo’s home was perfect for our needs. We had plenty of room, places to enjoy together, and space where everyone could find some peace and quiet. The location was ideal. We were within an easy driving distance of all excursions and restaurants and could even walk to Island Fish Company, which was one of our favorites. Gerardo was extremely responsive. He checked in prior to our arrival and touched base a couple of times to make sure there was nothing we needed. An excellent home I recommend to others with no hesitation!!
Guest favourite
Townhouse in Key West
5 out of 5 average rating, 25 reviews

Sea Captain's Haven at Truman Annex

JaquelineRating, 5 stars2 months ago
Beautiful place with a pool right when you walk out. Stunning neighborhood- close to everything. We absolutely loved it here. Staff was super attentive and helpful and we really felt like we were home. A+ experience.
Superhost
Condo in Key West
4.78 out of 5 average rating, 65 reviews

Casa Papa Del Mar Ocean Front 1800 Atlantic Spectacular

GeorgeRating, 5 stars6 months ago
The sunsets from the balcony are amazing. Overall the place was relaxing and georgious.
Top Guest favourite
Condo in Key West
5 out of 5 average rating, 32 reviews

EYW Getaway

JesseniaRating, 5 stars1 week ago
We had a great stay! The place was clean, comfortable, and had everything we needed. The location was perfect, and communication with the host was smooth and easy. Would definitely stay here again, highly recommended!
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 months 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!!
Superhost
Condo in Key West
4.84 out of 5 average rating, 38 reviews

Henry's Piece of Paradise On The Ocean In Key West

DonaldRating, 5 stars2 months ago
Our stay was great. We had detailed instructions, the unit itself was decorated nicely, and the amenities within the building were great (pool and spa). Also the private beach area and walkability to food, snacks, restaurants was great!
Superhost
Home in Key Colony Beach
4.82 out of 5 average rating, 157 reviews

Waterview from three sides, Cabana Club, 30' Docks

NoraRating, 5 stars3 weeks ago
A Perfect Getaway! Our stay at this fabulous Airbnb was nothing short of amazing! The house was beautiful, clean, and offered breathtaking panoramic views of the open water. Waking up to the sunrise over the water was absolutely unforgettable. Brad, our host, was fantastic—super responsible, quick to respond, and incredibly easy to communicate with. He made the entire experience smooth and enjoyable from start to finish. The location was ideal for anyone who loves peace, nature, and especially fishing. We had plenty of opportunities to fish right from the property, which was a huge bonus. Highly recommend this place to anyone looking for a relaxing waterfront escape. We can't wait to come back!.

Family- and pet-friendly home rentals

Superhost
Campervan/RV in Big Pine Key
4.55 out of 5 average rating, 20 reviews

Bring your own RV. Our lot your Camper B5 No Tents

KevinRating, 5 stars3 months ago
It is a great place just a little tight getting the camper in The neighbors are all very friendly and helpful
Top Guest favourite
Home in Marathon
4.89 out of 5 average rating, 37 reviews

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

LydiaRating, 5 stars9 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
Home in Cudjoe Key
4.63 out of 5 average rating, 166 reviews

Ocean Front Home in Great Location

HaroldRating, 5 stars2 weeks ago
This booking was great for what we needed, thank you to the responsive hosts and pet friendly house that made our vacation that much better.
Superhost
Home in Marathon
4.62 out of 5 average rating, 26 reviews

Sweet Retreat

LoriRating, 5 stars38 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!
Superhost
Townhouse in Marathon
4.94 out of 5 average rating, 33 reviews

Waterfront luxury Villa (59) with sunset views and boat slip

ThomasRating, 5 stars52 months ago
The townhouse was in a beautiful location and was very clean. The kitchen was supplied with spices and some basic needs until you went grocery shopping. We had a very nice time and could sit on the back porch and look at the awesome view every minute of the day! There was a lovely pool on the property and anything we wanted to do was conveniently located to the property. We would love to come back!
Guest favourite
Villa in Marathon
4.88 out of 5 average rating, 58 reviews

New Paradise On Sombrero Beach

JenniRating, 5 stars1 month ago
The house was well equipped with all of the essentials. We had 8 adults and plenty of room. We did have to wash towels a few times, and buy more laundry soap, but the washer and dryer were conveniently located on the main level. The pool was smaller than what the pictures showed, but it perfectly suited our needs. All members of our party viewed the listing before we booked it and none of us realized it was a twin home. However, there is tons of privacy and the only times we noticed we had neighbors was when the shared dock was used. We had to buy a cooler (for poolside and the beach) and beach chairs. There were some pool floaters left behind, from previous guests that we used. The interior of the home is beautiful, with high ceilings and comfortable furniture. This is in a great location - close to grocery stores, restaurants and Sombrero beach! Monica was great to work with!
Superhost
Home in Marathon
4.4 out of 5 average rating, 5 reviews

One Particular Harbor ~ Pool Home, 110' Dock

DianeRating, 5 stars2 months 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, 162 reviews

Vida De Aqua - Water Life!

LauraRating, 5 stars1 week ago
Despite rain and windy weather the first part of the week, we had a relaxing and fun time. Really loved the tiki in the backyard, and watching manatee and tarpon in the canal. The home was lovingly decorated with personal artwork and clean. The hosts were very accommodating and quickly responded to questions. We also liked that we could walk to restaurants, and the grocery stores were also nearby.

Family-friendly home rentals with a pool

Guest favourite
Townhouse in Marathon
4.95 out of 5 average rating, 81 reviews

Life in Paradise in #1 Resort - Coral Lagoon

CameronRating, 5 stars2 months ago
We are glad we stayed here and would definitely stay again. The house was spacious, clean, and in good shape. Our kids loved the twin beds and they also loved the pool which was clean and warm. The outdoor seating areas were a nice touch, and the house was well appointed. I was a little disappointed to learn I could not use the dock in front of the place (due to maintenance), but the marina staff was very friendly and made the courtesy dock available to us for the boat we rented nearby. Would definitely recommend for small families.
Home in Marathon
4.89 out of 5 average rating, 19 reviews

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

BradleyRating, 5 stars10 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!
Home in Marathon
4.82 out of 5 average rating, 34 reviews

Waterfront, dock, easy ocean access, heated pool!

MelissaRating, 5 stars14 months ago
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:))
Home in Marathon
4.9 out of 5 average rating, 20 reviews

Villa Casa Cayo

AmyRating, 5 stars5 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.
Superhost
Campervan/RV in Big Pine Key
4.73 out of 5 average rating, 130 reviews

Tropical Caribbean Paradise and pool

JawwaadRating, 5 stars2 weeks ago
Great spot and location! Nice amenities and a clean place. Captain Rick was a great host and held great communication with us.
Top Guest favourite
Home in Key West
4.95 out of 5 average rating, 207 reviews

Lennon's Lodge, Luxury Accommodations for up to 6!

ChristinaRating, 5 stars2 weeks ago
Great find! I couldn’t recommend this place enough. The beds were comfortable, the place was super spacious. We loved the back yard and the jacuzzi. Communication with Naomi was great.
Condo in Key Colony Beach

3 Bedrm Condo on Ocean (7 day min.)

LourdesRating, 5 stars23 months ago
Our stay was amazing. The staff that runs the condo very friendly always cleaning all the common areas. Peter kept the beach areas clean every morning. Very quiet we rented kayaks and paddle that out to the sandbar every day. It was beautiful.
Condo in Key West
5 out of 5 average rating, 10 reviews

2 BR Condo Banyan Tree, Key West,FL

MaureenRating, 5 stars30 months ago
Place was nice and clean. We had a great time.

Destinations to explore

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