Family-friendly vacation rentals in Dukes County

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Dukes County family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
A spacious living area features a plush, white sectional sofa positioned around a decorative rug. Natural light enters through large windows adorned with arches. A wooden table holds a small vase with flowers, while an inviting fireplace enhances the cozy ambiance.
Apartment in Oak Bluffs
4.93 out of 5 average rating, 137 reviews

Victorian Oasis: Driveway, hot tub, grill & more

VictoriaRating, 5 stars2 weeks ago
This house had such an exceptional energy to it, it was so peaceful. The hosts are unbelievably welcoming and helpful! You can quickly tell how remarkable this place is. It was such a pleasure to stay in this house and explore the island this weekend. It was our first time on MV and it was wonderful. The beach was so close and relaxing, and amazing restaurants a just a short walk down the street! A huge thank you to the hosts for allowing us to stay in their beautiful home, it was just what we needed for a relaxing weekend.
Guest favorite
The open living area features a light-colored sofa paired with two armchairs, centered around a wooden coffee table. Bright natural light floods the space through large windows and sliding doors, which provide views of the outdoor patio and garden.
Home in Edgartown
4.98 out of 5 average rating, 65 reviews

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

HannahRating, 5 stars1 month ago
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!
Top guest favorite
A spacious driveway leads up to a custom-built house surrounded by trees. A large circular garden bed with dark mulch is accentuated by a flagpole displaying the American flag. Multiple buildings are visible, including a garage and a shed.
Home in Edgartown
4.99 out of 5 average rating, 78 reviews

Edgartown Beauty: The Perfect Retreat, Dogs OK

JaredRating, 5 stars4 months ago
Beautiful home! David gave perfect instructions for everything about the house and was very responsive. We all had a fantastic weekend, and will definitely be booking again! Thank you David!
Guest favorite
A charming two-story home is viewed from the exterior, featuring rustic wooden shingles and decorative green trim. A vibrant flowering bush adds a splash of yellow, contrasting with the home's muted tones. A well-maintained grassy lawn and trees frame the house, creating a peaceful setting.
Home in West Tisbury
5 out of 5 average rating, 25 reviews

Sunny Serene West Tisbury Contemporary

KellyRating, 5 stars9 months ago
This is our third time staying at Bruce's place and it is as lovely as ever. Bruce has always been quick to respond to any questions and when I happened to ask ahead of time if they had a blender he ordered one which arrived when we were there! Bruce has always been incredibly thoughtful and accommodating, and our kids also love this place. It has become a tradition for us and hopefully many more to come.
A sunlit corner of the guesthouse features a dining area with a round table and four wooden chairs, surrounded by large windows that offer views of the ocean. A decorative cabinet and television are positioned nearby, enhancing the inviting space.
Cabin in Falmouth
4.66 out of 5 average rating, 597 reviews

Waterside Guest House

ChristineRating, 5 stars1 week ago
What a gorgeous location! Pet friendly, peaceful and convenient.
Guest favorite
A rustic post and beam home is set amidst wooded surroundings, featuring a sloped roof with shingles. The exterior is accentuated by multiple windows and a spacious deck. Steps lead to a lower level, surrounded by natural landscaping and seating areas.
Home in Oak Bluffs
4.86 out of 5 average rating, 72 reviews

Oak Bluffs near beaches & town, A/C,Jacuzzi,kayaks

Cassie-LeeRating, 5 stars6 months ago
This is our third year staying at this beautiful home. I cannot say enough good things about it! The location is so peaceful and private. We love that there are so many places to walk and explore. My kids especially love the walk down to the lake. The house has everything you need for cooking and baking. And having the hot tub is a huge plus. Another great thing about this home is the location. It is close to both Edgartown and downtown Oak Bluffs!
An aerial view captures a seaside area featuring a long stretch of beach, bordered by calm waters. Several buildings are visible, along with a swimming pool area and a playground. The landscape includes greenery and accessible roads along the waterfront.
Condo in Falmouth

Surfside Resort Cape Cod, Falmouth MA

Family- and pet-friendly home rentals

Top guest favorite
The exterior of the renovated barn showcases a charming cottage-style design with gray shingle siding. A well-maintained lawn is surrounded by a variety of colorful flowers and shrubs, enhancing the natural setting. Large windows allow for ample natural light while adding character to the home.
Home in Chilmark
4.99 out of 5 average rating, 97 reviews

Renovated Barn in Chilmark 3BR

VickyRating, 5 stars8 months ago
As always, we had a wonderful time in Alexia's pristine, charming, well laid-out home. It suits our family perfectly, with its separate "wings" and its open common space. It's close to Menemsha and great walking trails. As a host, Alexia is always available and helpful. We had a relaxed and happy stay there!
Superhost
The exterior of a single-story house is depicted, featuring a landscaped yard with lush green grass and vibrant pink flowering bushes. A wooden front step leads to the doorway, framed by large windows that allow natural light into the interior.
Home in Edgartown
4.86 out of 5 average rating, 51 reviews

Edgartown Village/ Sun-filled Home/walk to town

JonathanRating, 5 stars3 weeks ago
Great location. Clean. Ann was very responsive. Everything as described. Overall a great place to stay
Guest favorite
The exterior of the home features a wooden deck with steps leading up from the grassy yard. The deck is surrounded by a railing and offers views towards the house, which has multiple windows and a shingle façade. A storage area is visible beneath the deck.
Home in Edgartown
4.76 out of 5 average rating, 66 reviews

Charming Edgartown Ranch

BrittneyRating, 5 stars10 months ago
The house is great for a group trip. It's roomy, charming, and in the perfect location if you want to walk to downtown Edgartown or use the local buses to navigate the island. The large back deck and outdoor shower were huge pluses! Nishi was kind, communicative, and offered flexibility with check-in and check-out times, which helped our travel plans run smoothly.
Guest favorite
The exterior of the house is surrounded by lush greenery, featuring a spacious yard with a picnic table and a stone wall. A guest cottage is visible, alongside a deck with outdoor seating and an umbrella. Tall trees provide shade on a sunny day.
Home in Oak Bluffs
4.93 out of 5 average rating, 60 reviews

First-class 4+ BR Lagoon Pond Camp

AndrewRating, 5 stars9 months ago
This home was perfect for our large family group. There are many places to gather upstairs, downstairs, on the big porch, and in the yard. The kitchen and living room are in the top floor. The kitchen has every cooking tool and pot known to humanity! We cook so this was a big plus. The home is steps from the lagoon, a deep bay on the north coast of MV. All of the bathrooms and bedrooms are on the first floor. The beds were comfortable, plenty of blankets and pillows were available. We would stay here again in a heartbeat!
Guest favorite
A modern kitchen is showcased, featuring dark cabinetry and granite countertops. Stainless steel appliances, including a microwave and dishwasher, are visible. A mosaic backsplash adds visual interest, while a brightly colored kettle sits atop the stove. An open doorway leads to a well-lit bathroom with framed mirrors.
Cottage in Oak Bluffs
4.9 out of 5 average rating, 201 reviews

Beautiful stroll to beach and all of downtown!

ZacharyRating, 5 stars1 week ago
great stay! super close to downtown oak bluffs, great area, all very walkable
Superhost
A grassy outdoor space features two blue Adirondack chairs and a small fire pit, surrounded by trees and overlooking a serene pond. A hammock hangs in the distance, while the deck is visible on the right, extending from the house.
Home in Oak Bluffs
4.83 out of 5 average rating, 196 reviews

Waterview, Private, Walk to Beach, Mile to Town

BrittneyRating, 5 stars3 weeks ago
Lisa's place is so lovely. It is so peaceful and has a great view. Check in was super easy and everything was as expected. Lisa is a great communicator and we were easily able to get questions answered. When we had an issue (not related to our stay) Lisa was so helpful and kind. Highly recommend.
Guest favorite
A wooden gate opens to a lush garden, framed by tall greenery and vibrant flowers. A pathway made of stones leads through the garden, offering a welcoming entrance to the cottage. Sunlight highlights the natural beauty of the space on a clear day.
Guesthouse in Edgartown
4.76 out of 5 average rating, 51 reviews

Marthas Vineyard 1BR Cottage 10 min to beach/town

RachelRating, 5 stars4 days ago
Great location, would definitely stay again
Guest favorite
A wooden pier extends over calm waters, leading towards a classic vintage house partially obscured by lush greenery. The sandy beach can be seen on the right, under a sky dotted with soft clouds, creating a serene coastal atmosphere.
Home in Edgartown
4.83 out of 5 average rating, 69 reviews

Spacious, Old Vineyard charm with Private Beach

KyleRating, 5 stars2 weeks ago
All I can really say is… wow!! From the moment we arrived, Liza was incredibly communicative, accommodating, and welcoming. And upon arrival, we recognized how truly special her home is; with so much character and charm! It’s very private and felt incredibly safe. The home seems nestled into Martha's Vineyard itself and the back led out to a private green space, dock, and beach with blooming bushes next to the path. This was such a rare find. It was so magical, we spent an afternoon painting watercolors of the view of the boats on the water that you can see from the living room. With six girls staying for a bachelorette weekend, we had an abundance of room. It is more spacious than the photos capture. Situated in a prime location near Edgartown. And every piece of decor, plate, bowl, cup felt vintage, special, unique. This place has authentic charm. Bottom line: Our stay was incredible. We all can’t wait to come back again!

Family-friendly home rentals with a pool

A private pool is surrounded by lush greenery, with two lounge chairs positioned on a concrete patio. The pool's clear water glimmers under sunlight, inviting relaxation amidst a serene outdoor setting.
Home in Edgartown
4.88 out of 5 average rating, 32 reviews

4 Acre Retreat w/ Pool

IsabelleRating, 5 stars34 months ago
A magical spot indeed! We stayed for 4 perfect nights and we enjoyed ourselves immensely. The grounds are very pretty, with wild turkeys visiting for morning coffee. The kitchen is newly remodeled and stunning. The pool was a great find and there were plenty of nice towels and an outdoor shower. The host is lovely and the caretaker called to say hello as well so we felt very taken care of. A must visit! 10 stars!
A two-story country home is surrounded by a grassy yard and features a deck made of wooden slats. The exterior showcases a traditional design with wooden shingles and green accents on the doors. A clear blue sky provides a bright backdrop.
Home in West Tisbury
5 out of 5 average rating, 5 reviews

Charming Getaway Post&Beam Home Cozy and Sweet

SarahRating, 5 stars11 months ago
Our family stayed at Madi's place for our summer vacation. Madi was very responsive and communicative prior to our stay with local recommendations and instructions for the home and beach passes. Our family of 5 was comfortable and we had a wonderful time on MV. Would definitely return to Madi's place.
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 stars10 months ago
Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.
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
4.92 out of 5 average rating, 48 reviews

Private 3bdrm Condo Tashmoo Woods

MaryRating, 5 stars9 months ago
Barbara’s condo was roomy and comfortable. We fell in love with the screened in porch. Lovely room for a cup of coffee in the mornings and a glass of wine in the late afternoon. We took a short ride through the woods to the town beach which led us to beautiful views of Tashmoo. We had a great time!
A two-story house with a shingled exterior is surrounded by trees. A screened-in porch extends from one side, offering a shaded space. A grill is positioned on the porch, and a grassy area is visible nearby.
Home in West Tisbury
4.75 out of 5 average rating, 8 reviews

West Tisbury Beach House

CaryRating, 5 stars11 months ago
Lovely location and very clean. Good spot to travel qround island. Lambert Cove was beautiful at sunset. If you have a bad back you might want to bring a mattress pad.
Condo in Oak Bluffs
4.92 out of 5 average rating, 13 reviews

Spectacular Martha's Vineyard Island Home!

StephenRating, 5 stars26 months ago
Thank you for your hospitality. The stay was great and you were a pleasure to deal with.
Guest favorite
A clear blue swimming pool is framed by a lush green tree and surrounding foliage. Poolside lounge chairs are positioned around the edge, alongside an umbrella providing shade. The vibrant sky is dotted with fluffy white clouds, enhancing the serene outdoor setting.
Cottage in Edgartown
4.98 out of 5 average rating, 97 reviews

Lovely two - story private cottage.

CarolRating, 5 stars9 months ago
We cannot say enough about this special place. Everything was perfect. It was everything we could have asked and more. This cottage has absolutely everything you would ever need. The location is wonderful. Linda has thought of everything to make you feel comfortable. She is very responsive and caring. We will definitely be back next year, already looking forward!
Guest favorite
A communal outdoor swimming pool is surrounded by a spacious deck with numerous lounge chairs. The pool features a diving board and is bordered by trees, providing a natural backdrop. A clubhouse can be seen in the background, enhancing the community feel.
Home in Falmouth
5 out of 5 average rating, 66 reviews

Cape Cod Falmouth Getaway Close to Beaches Pool

CarolRating, 5 stars9 months ago
Very quiet and safe neighborhood that was close and convenient to many locations. The converted garage was a huge bonus for its ease to unload and load our bikes, bags and equipment. Large kitchen with modern appliances and cookware. Wonderful high top dining room table. Very responsive host!

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