Family-friendly vacation rentals in Dukes County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Dukes County

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

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Top guest favorite

The exterior of the barn features wooden double doors that provide access to the interior. A stone wall runs along the garden, accompanied by seating areas consisting of a picnic table and two chairs. Lush greenery surrounds the property, enhancing the secluded feel.

Guesthouse in Chilmark

4.95 out of 5 average rating, 100 reviews

Beautifully Renovated 1800s Chilmark Barn

Beautiful 2-story private barn in Chilmark on Martha's Vineyard. Secluded yet convenient. Perfect for a couple or a couple with older children (space not good for those with mobility issues). Downstairs living area, dining area, fridge, toaster, coffee maker, half bath -- shower is outside in the private garden. Loft-style sleeping area upstairs (2 private sections). 2 friendly labs and 5 chickens on premises. Walk to Chilmark Store, easy bus access. Walk-on pass to town beaches, no car pass

Indoor spacesFamilyDecor

Guest favorite

A bright and airy space features a comfortable queen size bed with light bedding, complemented by two modern bedside lamps. A dining table with two chairs sits nearby, and large windows provide natural light. Warm wooden floors enhance the inviting atmosphere.

Guest suite in West Tisbury

4.95 out of 5 average rating, 136 reviews

The Apartment Guest Suite. Private. Just Renovated

This beautiful guest suite is a 5 minute walk to the village of West Tisbury on Martha’s Vineyard and has a private entrance on the back wing of our newly renovated modern barn house. Surrounded by trees, beside a large meadow, this bright and airy 400 space has a sitting area and a full kitchen. Enjoy the outdoor shower and the outdoor sitting area. The location is centrally located and a short walk to a village, providing many amenities. Ask about our other guest suites if you are with others.

KitchenFamilyHiking

Guest favorite

A spacious living room is highlighted by a large grey sectional couch adorned with various throw pillows. A wooden coffee table sits in front, featuring storage compartments. Two abstract paintings in calming blues are displayed above the couch, while soft lighting illuminates the area.

Guest suite in Oak Bluffs

4.95 out of 5 average rating, 432 reviews

Lovely 2 BR Oak Bluffs Apartment

This 100% private apartment is on the first floor of a shared house where owners and their son live upstairs. There are no shared spaces. You have a private entrance and parking. The living room, bedrooms, bathroom, and kitchenette are bright and clean. It is exactly 1 mile from Oak Bluffs Center, a half mile from The Cottages and Farm Neck Golf Course, and a block from Tradewinds walking trails. Across the street is the bike path, & the bus stop is on the corner for easy island transportation!

Indoor spacesKitchenQuiet

Top guest favorite

A bright sleeping area features a spacious white bed with decorative pillows and bedside lamps. A small kitchen area with light-colored cabinetry is visible in the background, complemented by a large window allowing natural light. A cozy seating area adds to the warmth of the space.

Guesthouse in Chilmark

4.98 out of 5 average rating, 241 reviews

Beautiful Guest House in Chilmark

This newly renovated guest house is located in a quiet and very private setting in Chilmark. The guest house is located above the garage adjacent to the main house with a private entrance. It has a queen size bed with two oversized chairs. There is a full bathroom and outdoor shower. A small kitchen features butcher block countertops, stainless steel sink, refrigerator and 2 burner electric stove and island. Air conditioning and heat. The space comes with a walk -on-pass to Lucy Vincent Beach.

Indoor spacesFamilyAccess

Top guest favorite

An open studio layout is showcased, featuring a spacious bed with a metal frame. A cozy seating area is arranged with patterned cushions and a wooden coffee table. Natural light pours in through multiple windows, illuminating the warm wood flooring and inviting ambiance.

Guesthouse in West Tisbury

4.98 out of 5 average rating, 122 reviews

Vineyard Meadow Artist Studio

This lovely artist's studio is just steps from miles of trails. Walk to the beach or meander through the woods of Long Point Wildlife Refuge, experiencing the serenity of this still untouched corner of Martha's Vineyard. This studio includes a bathroom with a shower, a washer/dryer and a kitchenette. It is the perfect spot for a lone artist, a couple or a family to enjoy Martha's Vineyard any time of year. This property shares the driveway and parking with Vineyard Meadows Writer's Cottage.

Indoor spacesFamilyAccess

Top guest favorite

A sandy beach stretches along the shoreline, meeting the calm blue waters. People are seen enjoying the sun and swimming. Beach umbrellas and some distant structures are visible under a clear sky with a few clouds.

Guest suite in Falmouth

5 out of 5 average rating, 116 reviews

Location Location Location! Beach, Bike, Ferry

STEPS to beach, bike path, trails, restaurants, shopping, bus to MV Ferry Gorgeous studio/in law apartment, private entry, own parking + patio Open plan living/sleeping area + en suite bathroom Queen bed + queen sleeper sofa: sleeps max 4 Fresh linens, towels, personal care products, first aid, hairdryer, iron Mini kitchen w fridge, air fryer, microwave, toaster oven, dishwasher, cutlery, crockery, coffee maker Our famous home baked goodies! Coffee/tea/milk/sparkling water provided

KitchenIndoor spacesBiking

Guest favorite

The interior features a wooden wall with a triangular peak highlighted by a small window, allowing natural light to filter through. A pendant light hangs from the ceiling, complementing the rustic aesthetics of the space.

Guesthouse in Edgartown

4.91 out of 5 average rating, 113 reviews

Martha’s Vineyard Cottage - A Glamping Experience!

This is your vineyard home, where you can walk or ride a bike less than a mile to the beach or two into town. Get the glamping experience with kitchenette, A/C, an outdoor shower, a composting toilet, a queen bed in the loft and futon couch that can sleep two more in the living room. Enjoy outdoor games, outdoor seating, a Weber grill for bbq, tv, WiFi, cozy indoor space and more, right on the bike path with a bus stop for easy accessibility or free car parking. Whatever you want!

Indoor spacesKitchenQuiet

Top guest favorite

A spacious deck features two wooden Adirondack chairs facing a serene waterfront view of Vineyard Sound. Lush greenery surrounds the area, and the calm water reflects the soft hues of the sky, creating a peaceful outdoor setting.

Home in Woods Hole

4.93 out of 5 average rating, 131 reviews

Juniper Point Cottage With Ocean View

Charming Cape Cod cottage on a quiet semi-private road with beautiful views of Vineyard Sound. This inviting coastal retreat features 3 bedrooms, 2 private en-suite baths, 1 semi-private en-suite bath, a fully equipped kitchen, gas fireplace, cable TV, WiFi, and air conditioning. Relax on the second-floor deck with water views or enjoy outdoor dining on the patio with the BBQ grill. Conveniently located near the Martha’s Vineyard ferry, bus station, beaches, shops, and town.

Indoor spacesKitchenCleanliness

Top guest favorite

A modern kitchen features a spacious island with two black bar stools. Stainless steel appliances, including a microwave and toaster, complement quartz countertops. Natural light fills the space through large windows, revealing a glimpse of greenery outside.

Cottage in Oak Bluffs

4.97 out of 5 average rating, 186 reviews

111I Beautiful and walk to everything Oak Bluffs!

This is a beautiful cottage in the heart of Oak Bluffs! Walk to town, the inkwell beach and the harbor! This modern and comfortable space will be the perfect home base for you and your family. Enjoy all the amenities including central air. Coffee maker, full laundry, outdoor shower and a beautiful patio too. We are on property eager to make your stay as magical as possible. Please check the reviews of our other listings to see how guests enjoy our properties.

KitchenIndoor spacesPets

Top guest favorite

The exterior of the yurt showcases a circular wooden structure with large, rounded windows, complemented by a metal roof. A private yard features lush greenery, colorful flora, and outdoor seating arrangements, creating an inviting space for relaxation and outdoor activities.

Home in Oak Bluffs

4.93 out of 5 average rating, 316 reviews

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

Indoor spacesFamilyHeating

Guest favorite

A raised ranch is surrounded by lush greenery, with large windows allowing natural light to fill the interior. A spacious deck extends from the front, providing outdoor seating options. The home is elevated, partially obscured by surrounding trees, and features a charming sloped roof.

Home in Oak Bluffs

4.79 out of 5 average rating, 259 reviews

Central location for your vacation

An apartment in a peaceful Raised Ranch! Your Martha’s Vineyard sanctuary. Centrally located from nearby Vineyard Haven, Oak Bluffs, Edgartown and West Tisbury. Beaches and trails in close proximity. 8 minutes away from ferry. Great for family vacation, Island explorations, work trips, hosting wedding guests, wellness retreat, or just a simple gateway, this home will compliment your Martha’s Vineyard experience.

KitchenFamilyQuiet

Top guest favorite

The cottage, elevated on a wooden foundation, features cedar shake siding and large windows, allowing for natural light. Surrounding greenery includes leafy trees and a small shrub, enhancing the tranquil rural setting. A grassy area with stones outlines the cottage's base.

Guesthouse in West Tisbury

4.99 out of 5 average rating, 111 reviews

Country cottage walk to Alley's General Store

This sunlit summery cottage is in a very quiet, private and pastoral setting, situated 100 feet from the small Tiasquam River, with many birds chirping in the abundant vegetation and trees nearby. Because of the river's proximity, the cottage has a Composting Toilet. My wife and I live on the property uphill from the cottage. The property is in the countryside but a 5 minute walk to the local town center.

Indoor spacesFamilyAccess