Pet-friendly vacation rentals in Oak Bluffs

4.92 out of 5 average rating, 133 reviews

The historic property is displayed from the street level, showcasing its architectural charm with a multi-story design. A covered porch is visible, featuring ornate woodwork. Shops line the street, contributing to a lively town atmosphere. Clear skies and bright sunlight enhance the inviting appearance.

Apartment in Oak Bluffs

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?

Outdoor spacesWalkabilityGetting around

4.98 out of 5 average rating, 103 reviews

Arrowsmith Cottage-Oak Bluffs Near Eastville Beach

Welcome to Arrowsmith Cottage! If you are considering bringing your pet, please note - 1 small dog will be considered, but please first contact me directly (scroll down on the cottage's listing page and click on the "Contact Host" button), and tell me a little bit about him/her, as pets require homeowner's written approval and guest’s agreement to the pet fee (generally $100 per stay) and homeowners’ pet rules. Hosts are not responsible for listing inaccuracies due to Airbnb's own input or AI.

Outdoor spacesWalkabilityCheck-in

4.94 out of 5 average rating, 18 reviews

Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ

1 last summer week available! Tucked away on a quiet, private dead-end road in Oak Bluffs, this sun-filled three-bedroom retreat strikes the perfect balance: you’re close to everything the Vineyard has to offer (only 1 mile from Circuit Ave and OB Town Beach), yet the moment you turn onto that shaded dirt road, the outside world melts away. It’s the kind of neighborhood where kids can run freely in the yard, where the pace slows down, and where a vacation actually feels like a vacation.

PetsOutdoor spacesNearby

A charming cottage is framed by a lush garden with vibrant flowers. The front porch features two rocking chairs, inviting relaxation. Soft lighting emanates from inside, through the gothic-style windows, under a welcoming blue roof surrounded by greenery.

4.92 out of 5 average rating, 211 reviews

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

PetsWalkabilityQuiet

A charming two-story house is featured, showcasing shingle-style architecture and a welcoming front porch. White pillars support a broad balcony, while large windows allow for natural light. The well-maintained exterior is accented by a well-paved path and surrounding greenery.

4.98 out of 5 average rating, 55 reviews

Pinkletink Plantation

Your family will be close to everything when you stay at this centrally-located place. Less than a mile from the heart of Oak Bluffs and Circuit Ave., where you'll find all the famous restaurants, harbor & night life. A half mile from Eastville Beach (fabulous sunsets). Take a morning stroll around "the chop"-East Chop & walk or run a 5K. Less than 2.5 miles from Farm Neck Golf Club- & 2.5 miles to State Beach. It has a well equipped kitchen, laundry, outside shower, & back yard!

WalkabilityOutdoor spacesLaundry

A grassy outdoor space features two blue Adirondack chairs and a small fire pit, surrounded by trees and overlooking a serene pond. A hammock hangs in the distance, while the deck is visible on the right, extending from the house.

4.83 out of 5 average rating, 216 reviews

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!

WalkabilityOutdoor spacesShared spaces

4.94 out of 5 average rating, 233 reviews

A gravel pathway winds through a lush forest, flanked by tall trees and dense greenery. Brightly colored signage can be seen attached to some trees. A narrow dirt path leads off to the right, inviting exploration.

Guest suite in Mashpee

Cottage on the Bay

Welcome to our charming Cape Cod cottage nestled on the tranquil shores of Popponessett Bay! This cozy space has been cherished by our family for generations, offering a quintessential Cape Cod experience. Located on a private point, our cottage provides stunning bay views and a serene atmosphere perfect for relaxation. Conveniently situated between Popponessett Market Place (2miles) and Mashpee Commons (2.6miles) you're close to shopping, dining, and entertainment options.

WalkabilityPetsBiking

Guest suite in Oak Bluffs

A spacious outdoor deck features wooden furniture, including a dining table with chairs and lounge seating. An umbrella provides shade, and potted plants enhance the natural setting. The deck is surrounded by greenery, contributing to a serene outdoor atmosphere.

4.8 out of 5 average rating, 353 reviews

Cottage suite between the harbors: no minimum stay

Nestled between Oak Bluffs and Vineyard Haven harbors, our relaxing suite is a perfect way to extend your weekly rental, or to enjoy a day or two on this special island we call The Rock. Our cozy guest suite, newly renovated has two bedrooms, living space, kitchenette, full bath, deck with grill, outdoor shower, and footwash (hot H20), W/D (in unit) and a private entrance. An easy walk to town and beaches. Parking is available in our driveway. Enjoy our historic home!

Outdoor spacesWalkabilityQuiet

5 out of 5 average rating, 167 reviews

A charming two-story home is framed by vibrant greenery and colorful shrubs, with a paved pathway leading to the entrance. Solar panels adorn the roof, reflecting a commitment to sustainability. Lush grass and well-maintained landscaping create an inviting atmosphere.

Home in Falmouth

Private Pond-side Cape Cod Home

Charming 2 bedroom home located on Flax Pond. Enjoy a private sandy beach and dock. Swim, kayak, fish, boat (trolling motors only) and just relax. Enjoy the home’s spacious deck with comfortable seating for the whole family complete with chiminea for late night fires. 2 levels of lodging with central air. 2 full bathrooms, kitchen, dining room and great room. Minutes away from town beaches, bike path, golf, and shopping. Parking for approximately 4 cars.

Outdoor spacesWalkabilityHospitality

4.97 out of 5 average rating, 184 reviews

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

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.

WalkabilityPetsParks

Cottage in Chappaquiddick

A bright living space features white walls and a wooden ceiling with ample natural light. A round coffee table is centered in the room, surrounded by a sofa and wicker chairs. A side table holds a lamp, and a colorful artwork is displayed on the wall, with ocean views visible through windows.

5 out of 5 average rating, 16 reviews

Beachfront Cottage w. Yard + Town Access

Welcome to The Mizzen Cottage! Updated 1930's cottage on an ocean front compound on beautiful Chappaquiddick. Complete with a picturesque porch overlooking the outer harbor, side deck, outdoor shower, washer/dryer, dishwasher. Stunning views of the Edgartown lighthouse and Cape Poge. Access to a private beach. Access town with just a 10 minute walk (or 1 minute drive) to the Chappaquiddick Ferry, and be in downtown Edgartown in 15 minutes or less!

Outdoor spacesWalkabilityQuiet

4.96 out of 5 average rating, 313 reviews

The cottage is adorned with warm, glowing string lights that outline the roof and windows, creating a welcoming ambiance. A lush wreath decorates the front door, while charming wood paneling and multiple windows enhance the inviting exterior.

Cottage in Tisbury

Not Your Great Aunt's Island Cottage

In the heart Vineyard, 1930's cottage, lovingly updated by architect-owner. • Stylish decor, open floor plan, granite terrace • 2 blocks to Main St/harbor/ferry/town beach/playhouse • Central Air • Easily walkable to bike rentals, restaurants, shops, spa, library, mini-golf, etc. • Large yard with wood/gas grills, bocce, corn hole, beach chairs, fire pit • Outdoor shower • 3BR + sleeping loft

Outdoor spacesWalkabilityBathroom

Popular amenities for Oak Bluffs pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

5 out of 5 average rating, 28 reviews

A charming two-story cottage features a shingled exterior with a pitched roof. The inviting front porch is supported by wooden pillars and surrounded by lush greenery. A white picket fence encloses the well-kept lawn, creating a warm curbside appeal.

Home in Edgartown

Martha's Vineyard Cottage: Walk to Town and Beach

PetsOutdoor spacesFamily

4.9 out of 5 average rating, 60 reviews

Home in Edgartown

Edgartown Cottage By The Pond

Outdoor spacesWalkabilityComfort

The exterior of the house is surrounded by lush greenery, featuring a spacious yard with a picnic table and a stone wall. A guest cottage is visible, alongside a deck with outdoor seating and an umbrella. Tall trees provide shade on a sunny day.

4.94 out of 5 average rating, 66 reviews

First-class 4+ BR Lagoon Pond Camp

WalkabilityPetsBeach

An open-living area showcases a dining table with transparent chairs and a modern chandelier above. A cozy seating arrangement with a sofa and colorful cushions is visible. Light enters through multiple windows, illuminating the space and enhancing the white shiplap walls.

4.97 out of 5 average rating, 33 reviews

1/2 mile walk to Downtown Oak Bluffs

PetsOutdoor spacesAir conditioning

5 out of 5 average rating, 10 reviews

A two-story blue house is framed by a grassy yard, featuring neatly trimmed shrubbery and trees surrounding the property. A stone pathway leads to the front entrance, flanked by steps, creating an inviting access point.

Home in Tisbury

Vineyard Haven Escape

WalkabilityFamilyLocation

A welcoming porch is featured with a classic rocking chair positioned beside a vibrant display of blue hydrangeas. The wooden siding of the home and large windows create a cozy aesthetic, surrounded by lush greenery.

4.86 out of 5 average rating, 58 reviews

3 beds, 3 baths 1.5 Miles to Downtown and Beaches!

WalkabilityOutdoor spacesComfort

4.97 out of 5 average rating, 121 reviews

A clear view of Vineyard Sound is visible through the surrounding trees, showcasing the serene blue waters extending to the horizon. The gentle outlines of land can be seen in the distance, framed by lush greenery and a tranquil atmosphere.

Home in West Tisbury

Lambert's Cove, Water view, Beach pass, Ferry Tix

Outdoor spacesWalkabilityComfort

5 out of 5 average rating, 29 reviews

A two-story house is situated among trees with fresh green leaves. A wooden staircase leads to the entrance on the upper level, while a gravel driveway provides access to the home. The exterior features dark wood siding complemented by teal trim.

Home in Chappaquiddick

Chappy Beach House

Outdoor spacesWalkabilityLocation

Pet-friendly home rentals with a pool

3.6 out of 5 average rating, 5 reviews

A welcoming exterior view of a cape house, featuring a neatly maintained front yard with a white picket fence. Colorful hydrangea flowers are planted alongside vibrant greenery. A collie dog rests calmly on the grass, adding a friendly touch to the scene.

Home in East Falmouth

Near Association Beach & Pool

WalkabilityPetsAccess

4.89 out of 5 average rating, 9 reviews

A welcoming exterior view of a modern house is presented, featuring a well-maintained path leading to the entrance. Flanking the walkway, neat landscaping includes flowering bushes and a lush green lawn. A bright sun casts a soft glow over the façade, enhancing the inviting atmosphere.

Home in Mashpee

Mashpee Manor Pool House

PetsOutdoor spacesBackyard

4.96 out of 5 average rating, 28 reviews

An aerial view reveals a spacious bay front home surrounded by lush greenery. A large pool is visible in the backyard, with steps leading down to a beach area featuring kayaks. The residence is set in a tranquil, wooded environment.

Home in Cotuit

ShoestringBayHouse, waterfront & pool in Cotuit

PetsOutdoor spacesLaundry

4.85 out of 5 average rating, 68 reviews

A charming Cape-style house is surrounded by lush green grass, featuring a well-maintained front yard adorned with flower beds and small American flags. The entrance is highlighted by a decorative door with a wreath, framed by neatly arranged bushes. A single-car garage is visible on the right.

Home in Mashpee

Sunny Cape w/Private Pool, Steps to Private Lake

WalkabilityOutdoor spacesValue

4.92 out of 5 average rating, 49 reviews

A clear blue swimming pool is surrounded by lounge chairs positioned for relaxation. Lush greenery provides a natural backdrop, while a shaded area offers protection from the sun. Steps lead from the pool to a nearby structure, adding convenience for guests.

Condo in Tisbury

Private 3bdrm Condo Tashmoo Woods

PetsWalkabilityCondition

5 out of 5 average rating, 12 reviews

The exterior of the home is surrounded by lush greenery and features a spacious deck. A retractable awning provides shade over the seating area, while the charming wooden siding and multiple skylights add character to the structure. The clear blue sky enhances the inviting atmosphere.

Home in West Tisbury

West Tisbury Gem with Deck + Association Pool

Outdoor spacesComfortGetting around

Home in Sandwich

5 out of 5 average rating, 4 reviews

Coastal Colonial Oasis | Heated Pool | Fire Pit

DecorSleep qualityIndoor spaces

4.95 out of 5 average rating, 75 reviews

A view from the deck reveals a well-maintained pool area surrounded by lounge chairs and umbrellas. Adjacent to the pool is a tennis court, framed by greenery, providing a serene backdrop. The water sparkles under a clear blue sky, inviting relaxation.

Home in East Falmouth

Family + Dog Retreat | Fenced Yard + Pool + Beach

WalkabilityOutdoor spacesLayout

Private, pet-friendly home rentals

4.96 out of 5 average rating, 69 reviews

A two-story house is depicted, featuring a light-colored exterior with multiple porches and large windows. A spacious yard is visible, framed by greenery. The porches, supported by columns, provide outdoor seating, inviting relaxation. Power lines stretch across the clear blue sky above the structure.

Condo in Tisbury

Short Walk into Town - Nice Comfortable Reasonable

PetsWalkabilityHospitality

4.86 out of 5 average rating, 7 reviews

Cottage in Oak Bluffs

Family cottage close to town.

WalkabilityOutdoor spacesLaundry

Guesthouse in West Tisbury

A rustic studio cottage is presented with a sloped roof and blue siding. A wooden deck leads to the entrance, flanked by a garden with flower beds. A grill is visible on the deck, and a stone pathway meanders through the green yard.

5 out of 5 average rating, 41 reviews

Charming W. Tisbury Studio Guest Cottage

PetsWalkabilitySolo travel

4.83 out of 5 average rating, 23 reviews

A spacious patio area is arranged with colorful adirondack chairs in red, blue, and turquoise. A fire pit is centrally located, surrounded by cobblestone flooring. A large red umbrella provides shade over a lounge seating area, featuring a couch that invites relaxation.

Apartment in Oak Bluffs

Pet-Friendly Oak Bluffs 3BR | Deck & Fire Pit

WalkabilityOutdoor spacesHot tub

5 out of 5 average rating, 13 reviews

Cottage in Falmouth

High Tide at Falmouth Village Cottages (24)

PetsWalkabilityCleanliness

4.92 out of 5 average rating, 25 reviews

Cottage in Oak Bluffs

#Islandbeachrose. Walk To Beach and Town!

Outdoor spacesWalkabilityBackyard

5 out of 5 average rating, 37 reviews

A wooden arbor frames the pathway leading to the cottage entrance, which is highlighted by a bright yellow door. Soft pink petals cover the ground, creating a charming welcome. Lush greenery surrounds the pathway, adding to the inviting atmosphere of the entryway.

Cottage in Tisbury

Charming Cottage

PetsOutdoor spacesFamily