
Family-friendly holiday rentals in Dukes County
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Top-rated family-friendly rentals in Dukes County
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Lambert's Cove, Water view, Beach pass, Ferry Tix
Enjoy stunning views of Vineyard Sound from this cozy three bedroom two bath home in a quiet neighborhood just minutes from Lambert's Cove Beach. This upside down house has one bedroom on the main level along with a full bath and open kitchen, dining, and family room. The downstairs has another living space, two bedrooms, laundry room, and full bath. Enjoy family time in the open upstairs with water views, or retreat to the lower level living room for some separation, quiet time, or work space.

Loft Guest Suite in Modern Barn House
A beautiful guest suite on Martha’s Vineyard with a private entrance on the 2nd floor of the back wing of our newly renovated modern barn house. Surrounded by trees, beside a large meadow, this large 400 square foot suite has vaulted wood ceilings and skylights. Enjoy the outdoor shower and new outdoor sitting area. The location is centrally located, just off historic Music St, a short walk to a small town center which provides amenities. Ask about our other guest suite if you are with others.

Cape Cod Cottage Getaway!
Classic Cape Cod cottage perfect for a last minute getaway. Incredible location with the beach, Shining Sea Bike Path, The Knob, and Spohr Gardens all within walking distance! A five minute drive to Falmouth Main Street which offers amazing restaurants and shops. In the other direction, another five minute drive will bring you to the historical seaside village of Woods Hole, home to world renowned scientists, numerous beaches, restaurants, museums, an aquarium and the Martha's Vineyard Ferry.

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.

Sunny Studio Apartment on Martha's Vineyard
Our Sunny Studio is centrally located on Martha's Vineyard. A down-island location with an up-island feel. Open and airy studio with kitchenette and bath. The apartment has all the essentials. The apartment is located within walking distance of hiking and biking trails. A 10 to 15 minute car ride to any down-island town / beach. ***Please Note: Although conveniently located we are not within walking distance to Bars or Restaurants. We do recommend first time visitors rent or bring a car.

4-Season Guest House on Historic Chilmark Estate
Beautiful private guest house in Chilmark on Martha's Vineyard. Secluded yet convenient. Drive on pass to spectacular Chilmark beaches! Newly renovated and gorgeous. Great location - 10 minute walk to Chilmark Store. Full kitchen, living area, kitchen island/dining table, queen bed, day bed (not for sleeping), fireplace/heater, private outdoor shower, deck and picnic table, full bath inside. Keurig machine. 2 friendly labs/2 chickens on premises. Easy bus access. Old-style MV charm.

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

**Vineyard Vacation Retreat** -3 BR
Just a stone's throw from Oak Bluffs and it's beaches, this chic 3 bedroom home provides comfort and privacy. The large bedrooms and open concept kitchen/dining/living area accommodate up to 6 people comfortably. A place for you to put your feet up, kick away your worries, and enjoy some rest and relaxation. There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home.

Juniper Point Cottage With Ocean View
Charming Cape Cod cottage on semi-private road with and ocean view of Vineyard Sound. Renovations completed in mid-July, 2020. Three BR, 2 private attached baths, 1 semi-private bath, fully equipped kitchen, patio with BBQ grill, gas fireplace, cable-TV, WiFi internet, large second-floor deck, a/c.. Close to Vineyard Ferry, bus station and town. Seasonal rent. Please complete a reservation request to determine the rent in effect for your requested dates.

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!

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.

20-minute walk to Edgartown Village!
This 1550 square foot Ranch-style Condo with loft was built in 2018 and is set on a large nicely landscaped lot with plenty of room inside and out. It has It has 3 bedrooms and sleeps 8. It’s a 20-minute walk to the Edgartown village center, a 10-minute walk to Morning Glory Farm, and just a 10-minute drive to South Beach! All updated furnishings, beds, linens, appliances. Read our reviews! Immaculate!
Popular amenities for Dukes County family-friendly rentals
Family-friendly home rentals with a hot tub

Quiet West Tisbury 2 BDR Suite

Oak bluffs cottage Perfect place to honeymoon!

Ocean Front Resort Studio Unit

Valentine's Retreat Hot Tub Fire Pit Trails Beach

Walk to Beach • Hot Tub • Pet Friendly

Top-Rated Island Retreat: Hot Tub, Lamberts Cove!

Victorian Oasis: Driveway, hot tub, grill & more

Stunning 4/2.5 Water View, Hot Tub, Dogs ok
Family- and pet-friendly home rentals

Charming water-front cottage on Martha's Vineyard!

impeccable cottage STEPS to downtown OB & beach!

Saltwind Cottage | Beach Walk • Cozy Fireplace

Charming W. Tisbury Studio Guest Cottage

Chilmark Cape in private wooded setting

Sunny, Spacious Vineyard Retreat

Greenehill~ Up-island 1800's Vineyard farmhouse.

Waterview, Private, Walk to Beach, Mile to Town
Family-friendly home rentals with a pool

Relax....You're on Island Time......

Harborside Inn - 1BR Oceanview King Suite

Beautiful Family Friendly House with Pool

Private 3bdrm Condo Tashmoo Woods

Beautiful Edgartown 3500 sq ft home, heated pool

Sunny 2bedroom condo w pool, walk to town

Martha’s Vineyard Condo * Near Ferry

Luxury Retreat w Heated Pool, Large Stone Patio!
Destinations to explore
- Private suite rentals Dukes County
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- Apartment rentals Dukes County
- Rentals with outdoor seating Dukes County
- Rentals with a hot tub Dukes County
- Rentals with a firepit Dukes County
- Hotel rooms Dukes County
- Rentals with breakfast Dukes County
- Rentals with a patio Dukes County
- Pet-friendly rentals Dukes County
- Rentals with a fireplace Dukes County
- Rentals with a washing machine and dryer Dukes County
- Rentals with beach access Dukes County
- Waterfront rentals Dukes County
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- Bed and breakfasts Dukes County
- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
- Cape Cod
- Brown University
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- East Sandwich Beach
- Duxbury Beach
- Easton Beach
- Onset Beach
- East Matunuck State Beach
- Roger Williams Park Zoo
- Bonnet Shores Beach
- Coast Guard Beach
- Second Beach
- The Breakers
- Sandy Neck Beach
- New Silver Beach
- Pinehills Golf Club
- South Shore Beach
- Nickerson State Park
- Point Judith Lighthouse
- Popponesset Peninsula
- Lighthouse Beach
- Cape Cod Inflatable Park




