Family-friendly vacation rentals in Westport

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Westport family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favorite
Home in Centerville, Barnstable
4.97 out of 5 average rating, 153 reviews

Luxury House 0.25 mi from Craigville Beach

SarahRating, 5 starstoday
Came here for my sisters bachelorette. It was amazing . We felt right at home . It was very spacious and clean . Hosts thought of everything . Definitely would come back. The hosts were very responsive and very flexible. Great place to stay. The games and ping pong and air hockey tables were a hit !!
Top guest favorite
The exterior of a charming house is shown, featuring a gray shingle facade and a welcoming covered porch. Lush greenery and ornamental shrubs frame the entrance, while a gravel driveway leads up to the front door, creating an inviting approach.
Home in Oak Bluffs
4.94 out of 5 average rating, 194 reviews

Spectacular beach & pool combo; beautiful sunsets!

JillRating, 5 stars3 weeks ago
The house was beautiful, very comfortable and extremely well equipped. I would highly recommend this home. We had a wonderful stay there!
Guest favorite
The living room features a light-colored sofa and an armchair positioned on a patterned area rug. Natural light enters through arched window frames, illuminating the space. A coffee table sits in the center, and a piano is visible in the background, adding to the inviting atmosphere.
Apartment in Oak Bluffs
4.93 out of 5 average rating, 135 reviews

Victorian Oasis: Driveway, hot tub, grill & more

EmilyRating, 5 stars7 months ago
This was our second time renting this property. We had a lovely adults weekend, and really enjoyed our stay.
Superhost
A spacious backyard is shown, featuring a wooden playset with a slide and swings. Lush greenery surrounds the yard, with tall trees providing shade and privacy. The grass is well-maintained, creating a suitable area for outdoor activities.
Guest suite in Canton
4.72 out of 5 average rating, 106 reviews

Newly renovated, close to Foxboro and Boston

MeganRating, 5 stars6 months ago
The host communicated well and was very thoughtful. The bed wasn't very comfortable and the heating unit was a bit tricky to figure out, but overall, we had a great stay.
Guest favorite
An overhead view of the living room displays a light-colored sofa paired with two accent chairs, all arranged on a striped area rug. A wooden coffee table sits at the center, with large windows letting in natural light and patterned curtains framing the scene.
Home in Edgartown
4.98 out of 5 average rating, 61 reviews

On HGTV! Gorgeous, AC, Hot Tub, WALK Town & Beach

RachelleRating, 5 stars3 months ago
Marina’s home is Beautiful! The home was perfect for our stay. She has everything that you would need and extra. The location was great. If it had been warmer, we would have walked to town or took the bikes out. We definitely plan on returning!
Guest favorite
A contemporary kitchen features white cabinetry and a spacious island with seating. Modern appliances, including an oven and dishwasher, are visible. Natural light enters through a window, illuminating the marble countertops and the stainless steel range hood, enhancing the kitchen's functionality.
Home in East Falmouth
4.9 out of 5 average rating, 60 reviews

Peaceful waterfront home with dock/ hot tub

ConorRating, 5 stars8 months ago
We stayed at this home with a group of five people and the home fit everyone great. The view from the home of the marsh is beautiful and we spent Saturday hanging out on the dock. It is really peaceful and we had an amazing time. Michele was a pleasure to work with and was very accommodating with being flexible for check in and check out times. Thank you again!
Superhost
A charming two-story home is framed by lush greenery, featuring a sloped roof with solar panels. A driveway leads up to a spacious garage, while well-maintained gardens and neatly trimmed hedges enhance the inviting exterior.
Home in Plymouth
4.87 out of 5 average rating, 79 reviews

Amazing ocean front 3 bedroom

CrystalRating, 5 stars6 months ago
We had a wonderful stay! The house was great! Views were awesome from the top balcony! We wished the bushes and shrubs had been trimmed a little to have a better view from the main level but it was still a nice view from the one area there. House was quite roomy and had everything we needed in the kitchen. There are not tvs in the two spare rooms which would have been good after dinner for our teenagers while winding down after family time. The host is wonderful and communicated great. Overall we had a great family vacation and a good time. The house is nice. Would recommend!

Family- and pet-friendly home rentals

Guest favorite
A bright living area features a comfortable gray sofa and armchair, complemented by wooden flooring. Natural light fills the space through large windows adorned with light blinds. A granite countertop kitchen area is visible, offering modern appliances and a small dining space with a wooden table.
Condo in Newport
4.92 out of 5 average rating, 652 reviews

Boutique Hotel Special pricing available

KatherineRating, 5 stars1 day ago
Location is great - steps away from Thames St. It was clean and the staff are very friendly. They checked in daily to make sure we had everything we needed.
Superhost
Condo in Plymouth
4.77 out of 5 average rating, 154 reviews

Clear Pond Pet Friendly Inn

NicklausRating, 5 stars5 months ago
Friendly host! Allowed us to bring our 4 little dogs! Hard to find a host that will allow this. Clean and peaceful property.
Superhost
A well-lit bedroom features a spacious bed with a light blue and white patterned coverlet. A small lamp sits on a bedside table beside the bed. Natural light enters through a large window adorned with blinds, complementing the warm wall color.
Apartment in Newport
4.79 out of 5 average rating, 153 reviews

Downtown Hideaway! Walk to Harbor & restaurants.

AmyRating, 5 stars6 months ago
Great location and David was very responsive and helpful throughout the entire stay!
Superhost
A spacious outdoor deck area is surrounded by greenery, featuring wooden seating and a table complemented by a sun umbrella. The deck leads to a gravel pathway, accompanied by landscaped plants and a wooden fence, creating a serene outdoor atmosphere suited for relaxation.
Guest suite in Oak Bluffs
4.78 out of 5 average rating, 318 reviews

Cottage suite between the harbors: no minimum stay

MeganRating, 5 stars7 months ago
This was exactly what we were looking for--it was equal distant from vineyard haven and oaks bluff, right along the bus route. We ended up renting bikes and biking to and from different towns, which was amazing. Theda was extremely responsive and even let us check in and out when we needed. We'll definitely stay here again when we're in town!
Guest favorite
Home in Hopkinton
4.88 out of 5 average rating, 122 reviews

Large estate with pond near beaches

SaraRating, 5 stars4 months ago
This was a fabulous destination! We were looking for a big place to have a special anniversary party weekend with extended family, and this house had everything we needed. Plenty of bedrooms upstairs and first floor, many common gathering areas, large kitchen and dining room tables, and lots of Space. (And this doesn't even include the explorable property outside.) The dozens of photos in the listing were very helpful, as well as the detailed descriptions. We had specific needs for elderly relatives with disabilities, and owner Lynne was so responsive in her replies to my many messages with varied questions. Truly, Lynne, you deserve a gold star from Airbnb for promptness and offering up ways and help that made our stay both easier and fulfilling.
Guest favorite
The exterior of a classic New England-style home is displayed, featuring a mix of wooden shingles and siding. The structure has multiple windows, providing a view of the inviting entrance. A tranquil atmosphere is accentuated by the surrounding trees and clear blue sky.
Home in Newport
4.94 out of 5 average rating, 113 reviews

Peleg Barker House. Spacious & Family Friendly!

MichaelRating, 5 stars3 months ago
We had a wonderful off-season weekend at Jenny’s place. It’s a beautiful home that is well appointed, which made it easy to settle in. The house is also in a prime location in downtown Newport. Being mid-January, it was nice to have a short walk to many great restaurants and shops. We look forward to coming back!
Top guest favorite
A three-story house is nestled within a lush green yard, showcasing two expansive outdoor decks adorned with comfortable seating. Sunlight filters through trees, creating a serene atmosphere. The lower level features walk-out access, enhancing the connection to the outdoor space surrounded by natural landscaping.
Home in Tisbury
4.98 out of 5 average rating, 268 reviews

Sunny, Spacious Vineyard Retreat

LizRating, 5 stars4 weeks ago
This is the third time my family has stayed in this beautifully furnished and extremely comfortable home, located on a quiet cul de sac. Always perfect for our Vineyard get-aways.
Guest favorite
The open living area features a spacious gray sectional sofa adorned with colorful throw pillows. A coffee table with a plant and magazines sits within reach. Light wood flooring complements the inviting atmosphere, while the kitchen and dining area are visible in the background.
Home in Oak Bluffs
4.83 out of 5 average rating, 193 reviews

Waterview, Private, Walk to Beach, Mile to Town

LaurenRating, 5 stars6 months ago
We stayed at Lisa’s place for three nights and it was a 10/10 experience. Lisa was a fantastic host and was very helpful with island recommendations prior to our trip. The property itself is stunning and although we wanted to explore the island, the property also provided a beautiful landscape to just relax. Even given its private, peaceful location, it was still so convenient to town. The house is an adorable converted barn that has incredible, rustic charm and the decor was so beautifully thought out. Before we even left we were talking about booking again in the future. We definitely recommend booking here!

Family-friendly home rentals with a pool

Guest favorite
A clear, inviting pool is seen with a smooth surface reflecting the sky above. Lounge chairs are arranged neatly around the pool area, with several placed alongside a white picket fence. The tranquil setting is enhanced by distant views of the horizon.
Condo in Vineyard Haven
5 out of 5 average rating, 21 reviews

Relax....You're on Island Time......

JocelynRating, 5 stars8 months ago
Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.
Top guest favorite
A comfortable living area features a gray sofa complemented by a decorative white throw pillow. Light wood flooring is covered by a patterned area rug. French doors lead to a bright dining space, with natural light filtering through nearby windows.
Home in Plymouth
4.96 out of 5 average rating, 55 reviews

Our families slice of heaven

MarkRating, 5 stars6 months ago
Marla's vacation home was very lovely. We liked the pictures of her place, but once we arrived we realized that she had remodeled a number of rooms. Each room was updated, very clean and cozy. Marla has made sure that her place is stocked with all of the large and small conveniences that guests would want in a home away from home. The location and the surroundings are stunning, especially with the Fall foliage. One can tell that Marla takes great pride in her beautiful rental. -Mark & Susan G
Superhost
An above-ground pool is surrounded by a well-maintained wooden deck. A large inflatable unicorn and a colorful floating ring rest on the shimmering blue water, with trees providing a natural backdrop and sunlight reflecting off the surface.
Townhouse in Middletown
4.97 out of 5 average rating, 35 reviews

Townhouse Close to Downtown Newport & Beaches

WillaRating, 5 stars20 months ago
My family had a great weekend at Kristin’s house. I love this Beautiful, clean, well maintained property. The fire pit is great for marshmallow. We did not get to use the lovely pool because it got really cold at night. Bonus: filtered water from fridge, blinds + curtain, skylight in bathroom.
Guest favorite
A clear blue swimming pool is surrounded by lounge chairs positioned for relaxation. Lush greenery provides a natural backdrop, while a shaded area offers protection from the sun. Steps lead from the pool to a nearby structure, adding convenience for guests.
Condo in Tisbury
4.91 out of 5 average rating, 47 reviews

Private 3bdrm Condo Tashmoo Woods

JamikaRating, 5 stars8 months ago
What a relaxing and wonderful stay! Barbara’s place was welcoming and even better than the pictures. The house has everything you need and the addition of the community pool was the cherry on top. The host was extremely responsive and helpful. We look forward to returning to Barbara‘s place the next time my family and I visit MV.
Superhost
Townhouse in Mashpee
5 out of 5 average rating, 3 reviews

4th July week! Cape Cod Townhome

DmitryRating, 5 stars82 months ago
The place is great if you don't mind having to drive to a beach or to town. It's spacious and clean. And Ruth is a great host. She was very responsive.
Superhost
The outdoor area features a pool surrounded by a wooden deck, with a shaded gazebo nearby. Two white lounge chairs are positioned along the poolside, while colorful pool floats are visible in the water. A hot tub is situated beside the gazebo, enhancing the space.
Apartment in North Falmouth
4.79 out of 5 average rating, 108 reviews

Falmouth, Cozy Studio Near Old Silver Beach

Anna GraceRating, 5 stars8 months ago
We had a wonderful weekend stay! The house is located in a quiet neighborhood and the upstairs apartment was very clean. There is quick access to local beaches and restaurants. We would stay again!
Guest favorite
The entrance of the condominium is shown, featuring a wooden exterior with shingles. A pathway leads to the door, surrounded by neatly trimmed shrubs and grass. Bright sunlight highlights the clear sky and the inviting pathway.
Condo in Falmouth
4.73 out of 5 average rating, 15 reviews

Condo in Falmouth MA

RoberthRating, 5 stars1 week ago
Wonderfull place very peacefull and quiet . Beautiful lake in the Back as well. Patrick was very quick with his responses.overall great experience
Guest favorite
A private pool area is surrounded by lounge chairs and umbrella-shaded dining. The two-story house, featuring a light-colored exterior, is complemented by greenery and a spacious deck. Clear blue skies and sunlight enhance the inviting atmosphere of the outdoor space.
Home in Middletown
4.92 out of 5 average rating, 62 reviews

6/13-15 weekend open, Central AC, Walk 2 beach

EricRating, 5 stars1 week ago
Sara's place was fantastic! Perfect for our group running a local race. Walkable to Easton's Beach and restaurants in Middletown. the place is extremely comfortable and had everything we needed. Sara was excellent: very responsive and accommodating - I would definitely stay here again!

Quick stats about vacation rentals that are family-friendly in Westport

  • Total rentals

    70 properties

  • Nightly prices starting at

    ﺩ.ﺇ367 before taxes and fees

  • Total number of reviews

    2.5K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    70 properties include access to wifi

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