Kid-friendly holiday rentals in Osterville, Barnstable

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Osterville, Barnstable

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

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Guest favourite

Home in Chatham

4.96 out of 5 average rating, 124 reviews

Summerfell Cottage close to Ridgevale Beach

We have done extensive renovation and remodeling to the home with attention to detail. We believe we have created a warm and inviting atomosphere. The home is decorated in a coastal style with carefully chosen accents from the edison bulbs in the dining area to the custom barn/boathouse style door and repurposed hand hewn 18th century beam that anchors the staircase. The Kitchen is equipped with the same attention to detail for those who enjoy preparing their own meals. Summerfell is an entire home rental. Both hosts live nearby, Patty and Bill will be accessible via cell, text and email. The property is in a peaceful neighborhood with a good mix of seasonal homes and full time residences. The area has a number of quiet roads perfect for evening strolls. Of course, the beach is a short 5 minute walk away. The kitchen is equipped for the guest who enjoys cooking. From small appliances (Crockpot, waffle iron, blender, hand mixer etc) to small gadgets (citrus press, microplane, garlic press, potato ricer etc) A three burner weber gas grill is on the deck.

Top guest favourite

Flat 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?

Superhost

Home in Yarmouth Port

4.88 out of 5 average rating, 153 reviews

* Walk to the beach - Swiss Beach House! *

Walk to the beach! Less than a 1/2 mile (0.7 km)! Perfect spot for paddle boarding. Paddleboards and gas grill (available in summer). Private European - style house. Rustic charm. Laid-back atmosphere. 3 Bedroom, 2.5 bathroom. Comfortably sleeps 6-7, up to 8. Fire pit. Outdoor shower. Farm table for group dining. Fantastic central Cape Cod location. Natural environment. 15 min. to Hyannis for ferries to Nantucket or Martha's Vineyard. Enjoy something unique. Experience the real Cape Cod.

Top guest favourite

Home in Sandwich

5 out of 5 average rating, 28 reviews

The Cape Cottage Fireplace * Kid Friendly * PetsOK

The Cape Cottage is a private, tranquil Cape Cod-style cottage nestled near historic downtown Sandwich and just 6 minutes from the ocean. Newly renovated, this home is tastefully designed with a blend of coastal, farmhouse and antique design elements. We thoughtfully curated the home's details to evoke the comforts of home and give it unique charm that pays homage to quintessential New England and Cape Cod's scenic beauty. Check out our IG @thecapecodcottage for more pictures and vibes.

Top guest favourite

Home in Tisbury

5 out of 5 average rating, 15 reviews

Family Friendly 5 BR, Walk to Town, Beach & Ferry!

Ideal rental for families and friends! Two fully equipped kitchens, two fully furnished outdoor spaces, oversized deck with grill, washer/dryer, sleeps 10 (2 King, 2 Queen, Full over Full bunk beds) 3 living spaces, 2 pack and plays, 2 full baths, outdoor shower, large yard, and central a/c in every room! No ferry ticket? No car? No problem! This home is located close enough to the Vineyard Haven ferry for a quick bike ride or comfortable walk. Walking distance to trails and beach!

Superhost

Cottage in Barnstable

5 out of 5 average rating, 35 reviews

Charming Cottage, Walk to Beach, Whale Watch, Town

As seen on the pages of This Old House Magazine, The Cape Cod Times, & featured in a calendar of relaxing porches of Cape Cod, Sonny by the Sea is the perfect place to spend your vacation. Surrounded by all the beauty and charm of Cape Cod, but tucked into a quiet little neighborhood, there is so much to see and do that you could park your car and never use it again. Beautiful, super clean 2 bedroom, 1 full bath home with central air conditioning, wifi, linens, washer/dryer.

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.

Superhost

Home in East Falmouth

4.81 out of 5 average rating, 27 reviews

Charming Cape Oasis in Ideal Location!

Welcome to the Cape! Vacation like a true New Englander in this charming, exclusive, newly-renovated ranch home. Nestled in a quiet community, this Pottery-Barn style oasis boasts plenty of space and charm in an unbeatable location. Enjoy a private, fenced-in back yard with spacious deck creating a peaceful hideaway to enjoy drinks, coffee, tea, and nature. Minutes from beaches, shops, restaurants, and ferry to Martha’s Vineyard!

Superhost

Home in Dennis Port

4.8 out of 5 average rating, 56 reviews

Walk to Sea St. beach & restaurants - Cape Cod 👙⛱

Relax and unwind in this updated 4-bedroom, 2-bath coastal home in the heart of Dennisport. With space for 10 people, beachy decor, and plenty of outdoor space—including a brick patio with built-in firepit, and outdoor shower—it’s perfect for families and groups. Walk to multiple beaches, Ocean House Restaurant, and Sunday School Ice Cream. New England charm and modern comfort, all in one!

Top guest favourite

Home in Falmouth

4.94 out of 5 average rating, 307 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.