Family-friendly vacation rentals in Oak Bluffs

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Oak Bluffs family-friendly rentals

Family-friendly home rentals with a hot tub

A private backyard features a heated pool surrounded by a spacious deck. The contemporary two-story home, with large glass windows and doors, provides views of the lush greenery. Lounge chairs and umbrellas are arranged for outdoor relaxation.
Home in New Seabury
5 out of 5 average rating, 26 reviews

New Seabury pool/hot tub near beach,Popponesett

NicoleRating, 5 stars12 months ago
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.
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, 596 reviews

Waterside Guest House

AidenRating, 5 stars3 weeks ago
Super responsive, great host. Very friendly, offered us the local newspaper with deals on places to go and everything. incredible space, right along the water. Thank you, Ron!
Top guest favorite
The exterior of the house is surrounded by well-maintained greenery and tall, lush trees. A welcoming front entrance is framed by neatly trimmed hedges, leading to a slate pathway and steps. Large windows allow natural light to brighten the façade.
Home in Centerville, Barnstable
4.97 out of 5 average rating, 155 reviews

Luxury House 0.25 mi from Craigville Beach

AngieRating, 5 stars1 month ago
I had a wonderful experience staying at this Airbnb. The place was exactly as described—clean, cozy, and well-stocked with all the essentials. The host was friendly, responsive, and made check-in and out super easy. The neighborhood was quiet and felt very safe, with great local spots just a short walk or drive away. I’d absolutely stay here again and recommend it to anyone looking for a comfortable and convenient stay!
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

SaraRating, 5 stars4 days ago
My husband and I and our small dog had a fantastic stay. Sharon accommodated a (very!) early morning checkin time and was very responsive and clear throughout our stay. The unit suited our needs well and we absolutely loved spending time in the back patio/garden area.
The Great Room features soaring cathedral ceilings with exposed timber beams. A large stone fireplace serves as a focal point, surrounded by various comfortable seating options. Natural light fills the space through multiple windows, enhancing the inviting atmosphere.
Home in Centerville
4.78 out of 5 average rating, 51 reviews

Contemporary 5BR | Hot Tub | Dock

JobRating, 5 stars4 weeks ago
Our family stayed here after graduation and it was perfect
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 stars10 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!
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!

Family- and pet-friendly home rentals

Guest favorite
A spacious porch is framed by lush green foliage, creating a natural entrance. A large dog sits calmly on the wooden floor, while chairs and decorative lighting add to the inviting setting. A dining area is visible through the glass doors.
Home in East Falmouth
4.93 out of 5 average rating, 131 reviews

Summer House Close To Beaches

JulieRating, 5 stars6 months ago
Location was great and the neighborhood was quiet and beautiful. Robert was very responsive and accommodating. The ease of finding the home & access with the great directions along with a bottle of wine in the fridge were added bonuses after driving all day/night and a late night arrival.
Superhost
Home in Barnstable
4.84 out of 5 average rating, 170 reviews

Spacious house steps to Craigville beach! Dog ok!

DixitRating, 5 stars3 weeks ago
WE 12 friends went there for a long weekend getaway and we had a really good time. For anyone reading this review, one thing that this listing does not say is that how there are sun window in each room which is not covered by anything. So if you need dark room to sleep it will be an issue, some of my friends had hard time going to sleep once the sun was up and the room was all bright and lit. Beside that one issue we had an amazing time staying at this place. Olga is an amazing host and was always very responsive and understanding of our situation. The beach is at walking distance and the area is very safe, we loved going on a beach walk in the middle of the night.
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!
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, 272 reviews

Sunny, Spacious Vineyard Retreat

LindaRating, 5 stars1 week ago
Fran's house is lovely, everything one needs for a fabulous stay. She is a very good host - responsive and informative. She lives on the prpoerty but we never saw her. We had a really great stay!!!
Guest favorite
An open living area features natural wood flooring and soft blue walls. A round dining table sits beside a cozy seating arrangement, creating an inviting space. Large windows enhance natural light, and a modern kitchen area is visible in the background.
Home in Mashpee
4.92 out of 5 average rating, 143 reviews

Cape Cod; John’s Pond beach w/2 kayaks -SuperHost!

PinchasRating, 5 stars1 week ago
Very pleasant. Kristen oferred earlier checkin and very late checkout which allowed us to enjoy some additional hours at the beach and kayaking
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 stars1 week 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!
Superhost
A welcoming porch is featured with a classic rocking chair positioned beside a vibrant display of blue hydrangeas. The wooden siding of the home and large windows create a cozy aesthetic, surrounded by lush greenery.
Home in Oak Bluffs
4.84 out of 5 average rating, 51 reviews

3 beds, 3 baths 1.5 Miles to Downtown and Beaches!

WahidRating, 5 stars10 months ago
Lianna was absolutely wonderful and a pleasure to interact with; friendly, responsive and very helpful in providing tips and guidance; the home was cosy, well located, clean and well stocked / we really enjoyed our stay
Guest favorite
A charming cottage is surrounded by lush greenery and blooming hydrangeas. A small Weber grill is positioned on the stone patio, and a wooden pathway leads to the covered porch. The facade features multiple screened doors and windows, inviting natural light into the space.
Guesthouse in Tisbury
4.86 out of 5 average rating, 259 reviews

Adorable Vineyard Haven Cottage

LisaRating, 5 stars1 day ago
Cottage was exactly as described. Great location. We loved spending time on the porch, enjoyed the outdoor shower and all the hydrangeas were so beautiful!

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 stars33 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.
Top guest favorite
An in-ground pool is surrounded by a well-maintained yard, with vibrant green trees in the background. The pool deck features several lounge chairs and umbrellas for shade. The house is visible in the distance, with large windows that invite natural light.
Home in Mashpee
5 out of 5 average rating, 8 reviews

Beautiful Home w/ Pool, Fire pit and Game Room!

KimRating, 5 stars10 months ago
This was our family's first visit to the Cape, and the first time that mom had been back in decades. We had a wonderful stay! Mashpee was a great location - there was local access to good beaches and restaurants; but also a great location to access Sandwich and the Canal, Falmouth, Woods Hole and the Islands, all the way to Provincetown and everything in between. And we took advantage of it all over the week we stayed. Ed was a wonderful host! From booking until we checked out, he was very communicative, friendly, and had great information about local attractions and specialties. The property was very comfortable, and big enough for our family to relax and recharge. And our son loved the heated pool! We would definitely rent this or any of Ed's properties again!
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!
Top guest favorite
An open-concept living area features a plush gray sofa facing a glass coffee table. Four comfortable armchairs surround the table, while a kitchen is visible in the background. Large windows allow natural light to fill the space, with soft shades offering privacy.
Home in New Seabury
4.91 out of 5 average rating, 54 reviews

Private POOL*New Seabury*3 Bedroom

Jean PaulRating, 5 stars10 months ago
The home was pristine, more than what we could have asked for. Shelly was an amazing host, again, more than we could have asked for. You want a gorgeous home, with a stellar host, in the cape, with a private pool, amazing amenities, on a golf course and very close to the beaches, fun spots for kids, and shops, go to this place.
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.
Superhost
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
4.72 out of 5 average rating, 18 reviews

Condo in Falmouth MA

MarkRating, 5 stars1 month ago
The Condo was clean & comfortable. Having two bedrooms with queen beds was perfect for us, and sharing the 1 bathroom worked fine. The price was better than most other options. It was peaceful, and very quiet during our stay (in early May). Having the pool available would be very nice in summer months.

Quick stats about vacation rentals that are family-friendly in Oak Bluffs

  • Total rentals

    500 properties

  • Nightly prices starting at

    G$16,745 GYD before taxes and fees

  • Total number of reviews

    13K reviews

  • Pet-friendly rentals

    120 properties allow pets

  • Rentals with a pool

    30 properties have a pool

  • Rentals with dedicated workspaces

    230 properties have a dedicated workspace

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