
Vacation rentals with outdoor seating in Oak Bluffs
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Top-rated outdoor seating rentals in Oak Bluffs
Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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.

Vineyard Haven Walk to Ferry
I love this neighborhood! It is quiet, peaceful, and only a short walk to either Tashmoo Beach or downtown Vineyard Haven and the ferry. The house has plenty of outdoor space with it's own wood fired pizza oven, fire pit, and decks. There are nice seating areas near the fire pit, on the lower deck and on the upper deck. Walk through the backyard, down a dirt road and be at the water in five minutes. Beach towels included! Plenty of sliding glass doors and LOTS of light. Vitamix included!

impeccable cottage STEPS to downtown OB & beach!
Unique opportunity to stay in an impeccable cottage in Downtown Oak Bluffs. With a front porch with rocking chairs, a back deck & grill, & an outdoor shower, and A/C! - this is the ideal oasis for your Vineyard Vacation. Turn right and find yourself steps from restaurants & shops on Circuit ave. Turn left and walk 5 mins to beautiful beaches. Everything you want out of vacation at your fingertips. Relax, and truly experience the Vineyard the way it was meant to be, at the @WeePackemInn

Waterview, Private, Walk to Beach, Mile to Town
Rustic barn-style home, waterview, spacious natural landscape, serenity, and privacy on 3 acres centrally located 1 mi from Oak Bluffs and Vineyard Haven centers. Walk to beach, bike path nearby, comfortable interiors, memory foam mattresses, cotton linens, 2 HDTVs, high-speed wifi, heat/AC, 2 ocean kayaks, and 2 bikes. Location, amenities and privacy surrounded by natural beauty make staying very easy and relaxing. Ask the host about ferry reservations if they appear to be sold out!

Martha's Vineyard Getaway Cottage
Contemporary cottage on quiet, private, wooded lot. Pristine, bright & comfortably furnished. Open living area, hardwood floors, vaulted ceilings, indoor/outdoor fireplaces, well appointed kitchen, washer/dryer, cable/internet/phone with unlimited national calling, SmartTV with Netflix and additional internet streaming services. Walk or bike to beaches and trails, 5 minute drive from downtown shops and restaurants. Property abuts West Chop Woods with lovely, quiet walking trails.

Sweet little post and beam
A 700 sq ft post& beam guest house that sleeps 2 people. Open kitchen, living, dining area with full bath. Stairs lead to a full second story bedroom- a queen size bed, half bath, separate seating area. Private back patio and outdoor shower. Cozy off season cottage as well- radiant heat and AC. Central location to everything you want to see! Easy bike to town/beach. Very quiet and spacious. Everyone says "so much nicer in person than in the photos". Come see for yourself!

Unique Luxury Yurt w/ Free kayaking
Step into this unique yurt house! As soon as you walk in, you'll be greeted with a one-of-a-kind experience, from the textured concrete floors to the large circular skylight. Every detail is carefully planned, and you'll have the opportunity to unwind in a spacious private yard. Spend your evenings stargazing, take advantage of complimentary paddling, participate in our scheduled chicken feedings, do yoga in the roomy loft, and revel in the splendor of your exclusive island yurt!

** Vineyard Vacation Retreat ** with HOT TUB
Gated 2br house with lots of different places to lounge and relax. Drive through the 10’ granite gate onto the shell driveway. The house is filled with art from local artist Alan Whiting, Colin Rule, Kara Taylor and Scott McDowell. 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. Updated 7/25/2025 we do not have any more firewood on the property.

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.

Beautiful 3 bedroom in Oak Bluffs, walk to beach
Located in Martha's Vineyard, close to beach, bike path, oak bluffs center, art and culture, parks,and the airport. You’ll love my place because of the outdoors space with a wrap around farmers porch, the proximity to the ferry, walking distance to neighborhood beach, less than 2 miles from ferry, screened in porch, central a/c, hardwood floors and an open floor plan. Real Cape Cod feel with modern amenities. Most of my guest come back year after year!

The Lighthouse
Visit The Lighthouse! A passive solar, Bright and spacious contemporary home located in beautiful East Chop. Home is nicely appointed with 2-3 large bedrooms, 2 full baths, soaking tub. Outdoor shower and private tree lined yard with deck. Walking distance to semi private beach, town and ferry. Come relax in the window seat with a book. Have a glass of wine on the deck. Soak up the sun at the beach. This home provides true comfort!

Quiet Hide Away
Lovely efficiency suite with private entrance in a quiet neighborhood. Private space located over attached garage. Plenty of space for two guests. Comfortably appointed with queen bed, dining set, living area with tv and full bath. Enjoy a coffee or cocktail on the private deck. Toaster oven, refrigerator and coffee maker will start your day right before heading to nearby beaches, golf courses or shopping.
Popular amenities for Oak Bluffs outdoor seating rentals
House rentals with outdoor seating

Martha's Vineyard Cottage: Walk to Town and Beach

THE HAVEN: No car needed 0.4 m to downtown/beach.

Beautiful Oak Bluffs Cottage Close to Town

Walk to Downtown Oak Bluffs - Modern Cottage

Close to Edgartown Village Center!

New Pristine Luxury Home on Martha's Vineyard

Updated cottage/ ocean views

Newly renovated home in Oak Bluff near Farm Neck
Apartment rentals with outdoor seating

WATERFRONT PENTHOUSE OAK BLUFFS

Katama Loft

Brand new! Whole apartment, huge tub, full kitchen

Fantastic beach Ap 0.8 miles from Farm Neck Golf!

Stylish retreat | walk to town | fire pit

Cozy 3 bedroom apartment with King bed on Main St.

Apartment in Oak Bluffs

Your Private Garden
Condo rentals with outdoor seating

Heart of downtown, walk to ferry, bikeway & beach!

Private 3bdrm Condo Tashmoo Woods

Island Inn - Two Bedroom Suite - 1A - Oak Bluffs,

InnSeason Resorts Surfside

Beautiful condo with golf course views

Serene Cape Cod Escape w/ Private Ocean Overlook!

Spectacular Martha's Vineyard Island Home!

Heart of VH, w/ac, pool & harborview
When is the best time to visit Oak Bluffs?
Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
---|---|---|---|---|---|---|---|---|---|---|---|---|
Avg. price | R6,873 ZAR | R6,873 ZAR | R6,305 ZAR | R6,718 ZAR | R6,804 ZAR | R8,492 ZAR | R10,370 ZAR | R11,731 ZAR | R7,752 ZAR | R6,374 ZAR | R6,890 ZAR | R6,873 ZAR |
Avg. temp | 0°C | 0°C | 3°C | 7°C | 12°C | 17°C | 21°C | 21°C | 18°C | 13°C | 8°C | 3°C |
Quick stats about vacation rentals with outdoor seating in Oak Bluffs
Total rentals
390 properties
Nightly prices starting at
R689 ZAR before taxes and fees
Total number of reviews
16K reviews
Family-friendly rentals
320 properties are a good fit for families
Pet-friendly rentals
100 properties allow pets
Rentals with a pool
20 properties have a pool
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- Rentals with outdoor seating Dukes County
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- Cape Cod
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Point Judith Country Club
- Duxbury Beach
- Easton Beach
- Onset Beach
- Oakland Beach
- Horseneck Beach State Reservation
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