Family-friendly holiday rentals in Osterville, Barnstable

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Osterville, Barnstable

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite

Apartment in Oak Bluffs

4.92 out of 5 average rating, 109 reviews

Absolute Best Location on the Island

Ideal location for visitors in the middle of the most lively, diverse, fun town on Martha's Vineyard. This property is certified by the United States Department of Interior as a National Historic Property. The ferry terminal, restaurants, shops, markets, harbor, historic sites, entertainment, public transportation, and a clean sandy beach are all within minutes. A vehicle is not necessary. IF UNAVAILABLE: SIMILAR WALKABLE SISTER PROPERTY in Vineyard Haven: https://www.airbnb.com/rooms/49016488?

Top Guest favourite

Home in Brewster

4.99 out of 5 average rating, 112 reviews

Perfect Cape Cod vacation home

SUPER LOCATION for biking & hiking! Quiet neighborhood with direct access to 31 mile Cape Cod Rail Trail, 1900 acre Nickerson State Park and local clam shack / ice cream shop. Easy walking / biking access to Linnell & Crosby Landing Cape Cod Bay beaches and Flax & Cliff Pond fresh water beaches. Easy drive to towns of Orleans, Chatham, Harwich & Dennis. Whether it's a quiet walk, an exhilarating bike ride, salt or fresh water beaches, or a comfortable place to relax, this house has it all!

Top Guest favourite

Cottage in Harwich Port

4.95 out of 5 average rating, 358 reviews

Newly renovated Cape Coddage! Location! Location!

Newly renovated! Harwichport home- 2 min walk to beach, sleeps 10. Located right by Bank St Beach In Harwichport! Walk 1-2 minutes to the beach or walk 1-2 minutes in the other direction to Main Street where you will find shops and restaurants. Ember, The Port, 3 Monkeys, Beer Garden, and Mad Minnow. This home is in the dream location. Pull in and you don't need to drive until you leave. Walkable to Wychmere beach club. This home is often shared by guests of events celebrated at Wychmere.

Guest favourite

Cottage in Bourne

4.79 out of 5 average rating, 103 reviews

Adorable Gray Gables Beach Cottage

Adorable beach cottage in Gray Gables! This very charming home features a private back patio and outdoor shower. Updated kitchen and bathroom, laundry in unit. The living room features Cathedral-ceilings, a loft, and great natural light. Beautiful and lush plantings surround this warm and comfortable home - the perfect getaway! The sunroom is another great area and makes the space feel much larger. Steps to Gray Gables beach and the Mashnee Dike. Perfect for a Cape Cod family vacation!

Superhost

Cottage in Fairhaven

4.83 out of 5 average rating, 218 reviews

Cottage by the Bay

Cottage in Fairhaven, perfect for a vacation for a small family, a romantic getaway or a home away from home if you are in the area for business. Enjoy all a vacation has to offer. During warmer weather, walk to the public beach and boat ramp - swim, sun, boat. Spend evenings by the outdoor fireplace. When it is cold out side, enjoy parks, museums, arts and cultural events, with evenings spent enjoying hot chocolate in front of the gas stove as the fire blazes providing a cozy warmth.

Guest favourite

Home in Hyannis

4.9 out of 5 average rating, 462 reviews

Beach House, Harbor View and Family Friendly.

Our house is a stones throw from the beach. The harbor, Hyannis, downtown, cafes, restaurants, anywhere from 5 star dining to family-friendly dining are all in walking distance. Several family friendly activities are very close. You’ll love our place because of the walk to the family friendly beach, the ambiance, the ocean view and the neighborhood feel. Our place is good for couples, solo adventurers, business travelers, fishermen, families (with kids) and large groups.

Top Guest favourite

Cottage in Hyannis

4.99 out of 5 average rating, 142 reviews

Beach Glass Cottage - Pond Front

Come stay at the Beach Glass Cottage! A pristine pond front, completely renovated and tastefully decorated, 3 bedroom, 2 bathroom cottage in the heart of Hyannis. Truly the perfect get-a-way for family and friends. The Beach Glass Cottage is tucked away from the action, but within walking distance to Main Street Hyannis, which features eclectic shops, restaurants, bars, ice cream with mini golf and the Cape Cod Melody Tent is a short walk from the cottage as well.

Guest favourite

Cottage in Hyannis Port

4.92 out of 5 average rating, 119 reviews

Beautifully Updated, Classic Cape in Hyannisport

NEWLY RENOVATED KITCHEN & LIVING ROOM Within 1/2 mile to the beach, historic Hyannisport, downtown Hyannis Main Street, restaurants, Melody Tent and nightlife. -New mattresses on beds. Private setting. Very quiet neighborhood. Includes Beach Parking Pass -($25 daily) for all Barnstable Beaches. Great for families & groups over the age of 25. * Sheets, towels, beach chairs, and much, much more * No parties, excessive noise , pets, or smoking permitted.

Top Guest favourite

Cottage in Yarmouth

4.94 out of 5 average rating, 108 reviews

Cape Cod charmer 5 minute walk to Ocean beaches

Your oasis to relax, quite street, private back yard with large deck, gas grill, outdoor shower, breezeway and front deck. About a 5 minute walk to two ocean beaches on Nantucket Sound. Enjoy your morning coffee on a park bench as the sun rises over the ocean. Walking distance via sidewalk to beaches, seafood restaurant, Bass River beach pier and Joshua Baker windmill. Saturday to Saturday weekly rentals from late June to early Sept.

Top Guest favourite

Cottage in West Yarmouth

4.84 out of 5 average rating, 237 reviews

Charming Cottage near Beach and Ferry.

2022 renovation (floors, bathroom, cabinets) The cottage is only 150 yards from a sandy residential beach. Good for couples, families (with kids), and furry friends (pets). Enjoy a great outdoor shower, grill and deck, wifi, central AC/heat, cable TV, linens, washer/dryer. Additional Beach gear. No host interaction required. Great place to work remotely. Private yard and picnic table with lots of takeout options nearby.

Top Guest favourite

Home in Falmouth

4.94 out of 5 average rating, 308 reviews

Absolutely Adorable 4 Bedroom Ranch

Property is very close to beach at lovely, freshwater Jenkins Pond. This nicely furnished rental has a fabulous lower level family/TV room with add'l sleeping area and a full bath. Outdoors there is a large yard with a large deck and outside shower during the summer season. Minimum 2-night stay, rates may vary depending on season, weekly and monthly rate available.

Guest favourite

Home in Mashpee

4.96 out of 5 average rating, 184 reviews

Gorgeous sunsets! Private family beach - Cape Cod!

Saturday to Saturday weekly rental during summer months. Wrap around deck, beach and waterfront. Open layout. Perfect for families & Couples with a family beach . Stunning sunsets, very private and close to Mashpee commons, Falmouth and New Seabury all 10 minutes away. We are happy to have you for stays longer than 7 days! Just send us a note!