Family-friendly vacation rentals in Osterville, Barnstable

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Osterville, Barnstable family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
An open kitchen features blue cabinetry and stainless-steel appliances, with a large center island topped with a light-colored surface. Seating is provided by four metal stools. The adjoining living area is visible, showcasing a comfortable seating arrangement and natural light streaming through nearby windows.
Home in South Chatham
4.84 out of 5 average rating, 56 reviews

Perfect for Group w/ Kids & Dogs w/ Hot Tub

MackenzieRating, 5 stars2 weeks ago
This was my first time booking with a property management company so the reservation process was a bit more in-depth than normal but they are clearly very professional and experienced hosts. Overall we had an amazing stay for our girls trip. The house was beautiful and had plenty of space.
Superhost
A hot tub filled with clear water is positioned on a wooden deck, with soft lighting provided by string lights above. The exterior of the house is visible in the background, featuring large glass doors leading indoors and an area for outdoor dining.
Home in West Dennis
4.8 out of 5 average rating, 167 reviews

Walk2Beach, HotTub, FirePit, PetsOk

WilliamRating, 5 stars3 weeks ago
Very nice home, amenities were top notch. Definitely a good find if you're looking to stay in the area!
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.
Guest favorite
The exterior of a multi-level home is shown, featuring large windows and a wrap-around deck. A screened porch is visible on the lower level, while manicured grass surrounds the structure. The sky is clear, providing ample natural light to the setting.
Home in Dennis
4.92 out of 5 average rating, 50 reviews

Cape Cod Lakefront Home

JustinRating, 5 stars7 months ago
Nice private house with lots of bedrooms, a pool and nice grounds. House was very clean. We had a great time with our family. Can walk to a few places in town, but need to get into the car for most. The Dennis beaches were great and just a short drive away. Would recommend this place for families. The house has access to Scargo Lake, which is nice, but it is a bit of a hike down a good-sized hill. Host was nice and responsive to questions.
Top guest favorite
Home in Centerville, Barnstable
4.97 out of 5 average rating, 152 reviews

Luxury House 0.25 mi from Craigville Beach

LaurenRating, 5 stars3 weeks ago
We had a great weekend here. The entire house was very well clean when we arrived. The kitchen had everything we needed and the table was large enough to fit our entire group. We had a great time relaxing in the hot tub and game room. We would definitely recommend and book again.
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.

Family- and pet-friendly home rentals

Top guest favorite
The exterior of a Victorian semi-detached home is visible, showcasing a light blue facade, a screened-in porch with large windows, and manicured landscaping. A paved drive leads to a detached garage, while vibrant greenery frames the inviting entrance.
Guest suite in West Dennis
4.93 out of 5 average rating, 137 reviews

*Bass River Victorian Escape* Central A/C*WiFi

ErikaRating, 5 stars7 months ago
We had a wonderful week staying at Melissa and George’s Airbnb. The place was the perfect size for our family, a great place to hang out in between activities and had everything we needed. The screened in porch was heavenly and perfect for drying wet stuff from the beach. Lots of great amenities (chairs, boogie boards, etc) to use as well for our many trips to the beach and nearby lakes. Plenty of games to choose from too. The foosball table in the basement was a nice bonus. The hosts gave helpful recommendations and there was plenty of fun things to do within a short drive. Would highly recommended this place!
Superhost
Home in Brewster
4.86 out of 5 average rating, 126 reviews

Sun filled single level retreat, outdoor shower

AlexandraRating, 5 stars7 months ago
We had a really great stay and it was perfect for our group of friends to enjoy a wedding that was nearby. The home is comfortable and perfect for cooking and hanging out. Loved the backyard. The bed (at least the one in the master bedroom) was super comfortable for my bad back. Be sure to bring shampoo etc and you’ll have a wonderful time.
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
A shaded backyard space is equipped with outdoor seating arranged around a fire pit. A wooden deck is visible beside a tree adorned with blue lanterns, creating a relaxing environment. The grassy area is well-maintained, providing a comfortable setting for outdoor activities.
Home in Dennis Port
4.92 out of 5 average rating, 378 reviews

★ 0.4mi Beach &Village ★Firepit & Fireplace★ Bikes

JordanaRating, 5 stars2 months ago
We stay here often when visiting the Cape. Aruna is an amazing host and her home is lovely! I would definitely recommend staying here!
Top guest favorite
A private waterfront deck offers a serene view of Flax Pond, surrounded by lush greenery. Adirondack chairs are positioned for relaxation, providing a perfect spot to enjoy the tranquil waters and natural surroundings.
Home in Dennis
4.99 out of 5 average rating, 276 reviews

Stunning Waterfront! 3bdr/2bth/GasFireplace/kayaks

JenniferRating, 5 stars3 days ago
We drove up and thought it was going to be a tight fit for 3 adults, 2 teens and dogs, but we were wrong. We walked in and the first thing I notices was how clean and fresh it smelled. It was amazing! The place was spotless, the sofa was comfy, the area was great but the real show stopper....the view. Right on flax pond with gorgeous sunrises and relaxing evenings. My guys fished right from the deck....it was the perfect spot. Meg was amazing to work with as well. No surprises. Meg checked in leading up to the visit and after we left, but made sure we knew she was only a call away if we needed anything during our stay. Thank you Meg!
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!
Top guest favorite
A charming blue house with white trim and black shutters is situated behind a well-maintained garden. A stone pathway framed by colorful flowers leads to the front door, which is centered between two windows that provide natural light.
Home in Dennis Port
4.98 out of 5 average rating, 268 reviews

Shirley's Place - Pet Friendly Sleeps Six!

MeghanRating, 5 stars6 months ago
We loved our weekend at Karen's place! The house was cozy and clean, and had everything we needed for a comfortable stay (including treats for our pup)! The yard and deck were nice and private, and the house was conveniently located to many restaurants, shops, and not far from the water. Karen made us feel right at home!
Top guest favorite
A charming cottage features a light gray exterior with white trim and a welcoming front porch. Colorful flower beds surround the property, enhancing the natural landscape. Large windows allow ample sunlight to brighten the inviting atmosphere, framed by lush greenery.
Home in Brewster
4.98 out of 5 average rating, 187 reviews

SeaPeace Cottage-East Brewster Deck,Firepit,W/D AC

PaulRating, 5 stars6 months ago
We attended a wedding at the Ocean Edge Resort and we found Paige's home to be convenient to the venue and activities and a great alternative to staying on property. The home was clean and neat and had everything we needed. The weather turned out beautiful so we took full advantage of the outdoor space. I would highly recommend Paige's home to anyone who likes to be close to the beach, restaurants and golf, but far enough away to be quiet and peaceful.

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
Guest favorite
Home in Cotuit
4.94 out of 5 average rating, 18 reviews

ShoestringBayHouse, waterfront & pool in Cotuit

ZackRating, 5 stars6 months ago
Perfect stay - just be sure to bring or order sheets and towels!
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.
Top guest favorite
The image shows a private pool surrounded by a concrete deck, featuring a pool ladder on one side. Colorful pool floats are seen resting in the water, and a table with chairs is positioned nearby under an umbrella. Lush greenery borders the area, enhancing the serene environment.
Home in New Seabury
4.91 out of 5 average rating, 54 reviews

Private POOL*New Seabury*3 Bedroom

Jean PaulRating, 5 stars8 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.
Superhost
A clear blue swimming pool is surrounded by lounge chairs and bright blue umbrellas. The pool area is backed by several two-story buildings, featuring a blend of beachside architecture against a sunny sky. Green grass accents the poolside area, inviting relaxation.
Apartment in West Yarmouth
4.85 out of 5 average rating, 48 reviews

Ocean View 2-Bedroom Private Suite

LouisRating, 5 stars8 months ago
Good location ! Plenty to do and friendly service. I’d use them again
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 stars6 days ago
Wonderfull place very peacefull and quiet . Beautiful lake in the Back as well. Patrick was very quick with his responses.overall great experience

Quick stats about vacation rentals that are family-friendly in Osterville, Barnstable

  • Total rentals

    120 properties

  • Nightly prices starting at

    ﺩ.ﺇ477 before taxes and fees

  • Total number of reviews

    2.3K reviews

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with a pool

    20 properties have a pool

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

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