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

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

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.

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.

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.

WATERFRONT PENTHOUSE OAK BLUFFS
3rd fl Waterfront Oak Bluffs Harbor Penthouse- Sleeps 2 comfortably-3 in a pinch. (356sqft) . Queen bed & a reclining futon couch. With kitchenette & amazing harbor views, you cannot get closer to harbor, unless you fell in. Located above a seasonal restaurant, with 5 open air restaurants (2 on each side, & were in the middle with our restaurant Lobsterville Bar & Grille below)
Popular amenities for Oak Bluffs outdoor seating rentals
House rentals with outdoor seating

Juniper Point Cottage With Ocean View

Vineyard Cape Centrally Located Oak Bluffs, MA

Sunny, Spacious Vineyard Retreat

Close to Edgartown Village Center!

Serene Lakefront home in Cape Cod, #onlawrencepond

Martha's Vineyard Vacation Home

Bucolic, modern home near town, beaches

Newly Renovated! Seconds to sand, fire pit, A/C
Apartment rentals with outdoor seating

Katama Loft

Brand new! Whole apartment, huge tub, full kitchen

Top floor with views and steps to private beach

Clean private & cozy Cape Cod 1 br/ba with kitchen

Stylish retreat | walk to town | fire pit

Cozy Large Private Pet Friendly Studio

Apartment in Oak Bluffs

Discover the magic of Martha’s Vineyard! NEW !
Condo rentals with outdoor seating

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

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

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!

Cape Esacpe at New Seabury
When is the best time to visit Oak Bluffs?
Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
---|---|---|---|---|---|---|---|---|---|---|---|---|
Avg. price | R6,954 ZAR | R6,954 ZAR | R6,378 ZAR | R6,797 ZAR | R6,884 ZAR | R8,592 ZAR | R10,491 ZAR | R11,868 ZAR | R7,842 ZAR | R6,448 ZAR | R6,971 ZAR | R6,954 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 vacation rentals
Explore 390 vacation rentals in Oak Bluffs
Nightly prices starting at
Oak Bluffs vacation rentals start at R697 ZAR per night before taxes and fees
Verified guest reviews
Over 16,150 verified reviews to help you choose
Family-friendly vacation rentals
320 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 100 rentals that welcome pets
Vacation rentals with a pool
20 properties feature pools
Rentals with dedicated workspaces
210 properties have a dedicated workspace
Wi-Fi availability
380 of Oak Bluffs vacation rentals include wi-fi access
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Oak Bluffs rentals
4.8 Average rating
Oak Bluffs stays are highly rated by guests—averaging 4.8 out of 5!
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