
Family-friendly vacation rentals in Westport
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Top-rated family-friendly rentals in Westport
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Westport family-friendly rentals
Family-friendly home rentals with a hot tub

New Seabury pool/hot tub near beach,Popponesett
We stayed here for a bachelorette party and the house exceeded our expectations. Sherri was responsive and quick to answer all of our questions before and during the stay.

4th July week! Cape Cod Townhome
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.

Spectacular beach & pool combo; beautiful sunsets!
The house was beautiful, very comfortable and extremely well equipped. I would highly recommend this home. We had a wonderful stay there!

Victorian Oasis: Driveway, hot tub, grill & more
This was our second time renting this property. We had a lovely adults weekend, and really enjoyed our stay.

On HGTV! Gorgeous, AC, Hot Tub, WALK Town & Beach
We visited Island Grace for a long weekend and enjoyed the many perks of this beautiful home! It was a perfect spot to visit Edgartown, Oak Bluffs, and beaches and just a short drive to other areas and towns. We enjoyed biking, the hot tub, and the well-appointed kitchen. The beds were so comfortable! We truly had everything we needed and thought it was so fun to watch their HGTV episode!

Peaceful waterfront home with dock/ hot tub
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!

Amazing ocean front 3 bedroom
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

Boutique Hotel Special pricing available
Another great stay !! Clean , prompt & comfortable !

Clear Pond Pet Friendly Inn
Friendly host! Allowed us to bring our 4 little dogs! Hard to find a host that will allow this. Clean and peaceful property.

Raised Ranch Retreat: Modern 3 BR/3 Bath w/ Office
Brian was a great host, he was flexible and quick to respond. The home was nice and comfortable. There was a small issue with one of the bathrooms but no big deal. I brought to his attention just for awareness and he was apologetic. We enjoyed the home. I cook alot and the kitchen had what i needed except for things to use in oven and kitchen towels but otherwise well stocked. Great stay

Downtown Hideaway! Walk to Harbor & restaurants.
Great location and David was very responsive and helpful throughout the entire stay!

Cottage suite between the harbors: no minimum stay
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!

Rustic Retreat,unique home, minutes to Newport, RI
The rustic retreat was a cozy vintage inspired house that felt very homey. It was 5 minutes from great coffee shops and downtown Newport. It was great to be able to bring our dog. My daughter loved the secret bamboo garden ‘room’. Would definitely stay again. Lillian was very hospitable! Thank you!

Sunny, Spacious Vineyard Retreat
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.

Entire Home Close to Beach and Downtown!
Great location! Ronald was very responsive and helpful. Highly recommed!
Family-friendly home rentals with a pool

Relax....You're on Island Time......
Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.

Our families slice of heaven
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

Townhouse Close to Downtown Newport & Beaches
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.

ShoestringBayHouse, waterfront & pool in Cotuit
Perfect stay - just be sure to bring or order sheets and towels!

Private 3bdrm Condo Tashmoo Woods
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.

Falmouth, Cozy Studio Near Old Silver Beach
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!

Condo in Falmouth MA
Wonderfull place very peacefull and quiet . Beautiful lake in the Back as well. Patrick was very quick with his responses.overall great experience

6/13-15 weekend open, Central AC, Walk 2 beach
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
$100 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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- Boston Common
- Mayflower Beach
- Charlestown Beach
- West Dennis Beach
- East Sandwich Beach
- TD Garden
- Fenway Park
- Craigville Beach
- Duxbury Beach
- Harvard University
- Brown University
- Easton Beach
- Foxwoods Resort Casino
- New England Aquarium
- Sandwich Glass Museum
- Owen Park Beach
- Faneuil Hall Marketplace
- Sagamore Beach
- New Silver Beach
- Prudential Center
- Freedom Trail
- Onset Beach
- Blue Shutters Beach
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