Pet-friendly vacation rentals in Oak Bluffs

4.93 out of 5 average rating, 135 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

4.96 out of 5 average rating, 123 reviews

Home in West Tisbury

Lambert's Cove, Water view, Beach pass

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.

PetsWalkabilityHospitality

The exterior of a charming two-story house is viewed from the front, featuring a wrap-around porch adorned with hanging flower baskets. Lush greenery surrounds the entrance, and a clear blue sky looms above, enhancing the welcoming atmosphere of the property.

5.0 out of 5 average rating, 27 reviews

Updated cottage/ ocean views

Location! Location! Location! Leave your worries and car behind, this picture perfect Vineyard beach house is steps from downtown Oak Bluffs, the sandy beach and a few short blocks from the ferry. Recently renovated 3 bdr and1.5 baths, offering the perfect combination of cottage charm and modern updates. Enjoy ocean views from our wrap around porch and owner's suite enclosed balcony. Large backyard allows for private outdoor enjoyment. Prime location for enjoying all Oak Bluffs has to offer.

WalkabilityOutdoor spacesQuiet

4.98 out of 5 average rating, 104 reviews

Arrowsmith Cottage-Oak Bluffs Near Eastville Beach

Welcome to Arrowsmith Cottage! If you are considering bringing your small dog, please first contact me (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 dogs require homeowner's written approval and guest’s agreement to the pet fee and homeowners’ pet rules. We cannot allow cats, birds, or any animals other than one pre-approved dog. Hosts are not responsible for listing inaccuracies due to Airbnb's own input or AI.

WalkabilityPetsBeach

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.

4.97 out of 5 average rating, 61 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 spacesHospitality

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, 217 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!

Outdoor spacesWalkabilityShared spaces

4.96 out of 5 average rating, 109 reviews

The image captures a panoramic view of the ocean, surrounded by lush greenery. The tranquil blue water extends to the horizon, with a distant lighthouse visible on a rocky coastline. A clear sky overhead enhances the natural beauty of the landscape.

Home in West Tisbury

Lambert's Cove Oceanview Beach Pass Trails nearby

Traditional salt box home set in the forested hills above Lambert's Cove. Short walk / drive to town beach. Perfect for family gatherings, home has 3 bedrooms , a loft for virtual work space or reading room, 1.5 baths plus the fully enclosed outdoor shower, fully stocked kitchen, a deck that has seating for relaxing and also an octagonal picnic table, as well as lots of yard space for children or pups to play. Beach towels along with4 beach chairs provided.

WalkabilityPetsLocation

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.

5.0 out of 5 average rating, 28 reviews

Martha's Vineyard Cottage: Walk to Town and Beach

Updated 1920s Cottage in Edgartown Village – Walk to Beach, Harbor and Main Street Step into classic Vineyard charm at this fully updated 4-bed, 3-bath craftsman cottage in the heart of Edgartown. Two blocks from Main Street’s restaurants, galleries, and harbor and a quick walk to Fuller St Beach & Lighthouse Beach. Fully winterized + AC, high-speed Wi-Fi, three workstations. Ideal for families, bachelorette parties or anyone craving a New England coastal escape.

PetsWalkabilityBathroom

4.95 out of 5 average rating, 20 reviews

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

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.

Outdoor spacesWalkabilityIndoor spaces

The charming Cape Cod-style home is framed by lush greenery and a well-kept yard. A welcoming red staircase leads to the front door, while gravel paths and decorative stones outline the landscape, inviting guests to explore the outdoor space.

4.88 out of 5 average rating, 73 reviews

Oak Bluffs 4BR • 5 Min Drive to Downtown

Just 5 minutes from Downtown Oak Bluffs and nearby beaches, this spacious 4-bedroom home sleeps up to 8 guests and offers comfort, privacy, and a peaceful cul-de-sac setting. Enjoy an open-concept living area, fully equipped kitchen, private deck with BBQ, and large backyard with hot/cold outdoor shower. Both full bathrooms are newly renovated with floor-to-ceiling tiled showers and luxury top-shelf bath amenities for a spa-like experience.

PetsOutdoor spacesBathroom

4.9 out of 5 average rating, 125 reviews

Katama Barn

Selected dog friendly, Immaculate beach house this is the perfect property to bike to the beach and then to dinner in Edgartown. 1.2 miles from beach South Beach, and 1 mile from Edgartown's Main Street. Outdoor shower, large private yard.heated bathroom floors, a/c, heat, modern kitchen, brand new appliances/washer dryer, sleeping loft, and separate storage loft. Location, location, location.

WalkabilityOutdoor spacesLocation

4.96 out of 5 average rating, 317 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

WalkabilityOutdoor spacesSleep quality

Popular amenities for Oak Bluffs pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

5.0 out of 5 average rating, 170 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

PetsOutdoor spacesKitchen

4.97 out of 5 average rating, 166 reviews

The exterior of a charming multi-level home is showcased, featuring a spacious deck with seating and an umbrella. A stairway provides access to the upper level, surrounded by lush greenery. Large windows offer views of the wooded surroundings, creating a sense of integration with nature.

Home in Falmouth

Mid-Century Modern home 5 minute walk to beach

WalkabilityOutdoor spacesHiking

4.68 out of 5 average rating, 212 reviews

A spacious living area is highlighted by a large blue sectional sofa, complemented by several accent pillows. Large glass doors provide a view of the deck, while pendant lights hang from a vaulted wooden ceiling, enriching the open atmosphere.

Home in Tisbury

Carolyn's Vineyard Haven

PetsOutdoor spacesKitchen

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, 67 reviews

First-class 4+ BR Lagoon Pond Camp

Outdoor spacesPetsLaundry

The exterior of a single-story house is depicted, featuring a landscaped yard with lush green grass and vibrant pink flowering bushes. A wooden front step leads to the doorway, framed by large windows that allow natural light into the interior.

4.85 out of 5 average rating, 62 reviews

Edgartown Village/ Sun-filled Home/walk to town

PetsOutdoor spacesIndoor spaces

The exterior of the home is showcased, highlighting a spacious deck surrounded by natural landscape. Floor-to-ceiling windows illuminate the inviting interior, while a wooden structure features a mix of rustic materials. Outdoor seating and a picnic table are positioned for dining and relaxation.

4.87 out of 5 average rating, 46 reviews

Bucolic, modern home near town, beaches

WalkabilityOutdoor spacesBackyard

Cozy Carriage House Getaway — Steps to Oak Bluffs

WalkabilityOutdoor spacesBiking

5.0 out of 5 average rating, 33 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 *DERBY DATES!*

Outdoor spacesWalkabilityBiking

Pet-friendly home rentals with a pool

4.94 out of 5 average rating, 51 reviews

An aerial view of a spacious property featuring a uniquely shaped heated saltwater pool surrounded by a stone patio. A large deck is positioned next to the pool, with several lounge chairs arranged nearby and greenery framing the area.

Home in New Seabury

Coastal Charm New Seabury: 5BRs with Private Pool

Outdoor spacesWalkabilityBackyard

4.97 out of 5 average rating, 29 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 spacesPool

5.0 out of 5 average rating, 22 reviews

A serene backyard features a heated pool surrounded by paved stone decking. Multiple lounge chairs are positioned for comfort, offering views of the lush greenery. The two-story home is visible in the background, with a deck equipped for outdoor relaxation.

Home in New Seabury

New Seabury Oasis with Pool!

WalkabilityOutdoor spacesPool

4.92 out of 5 average rating, 50 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

PetsOutdoor spacesLong stay

4.95 out of 5 average rating, 82 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

WalkabilityPetsSleep quality

4.83 out of 5 average rating, 6 reviews

Home in Falmouth

Pool Escape in East Falmouth

PetsCheck-inPool

5.0 out of 5 average rating, 11 reviews

Tiny home in Sandwich

Cape Cod Resort|Cabin w/Pool & Private Beach

Outdoor spacesWalkabilityAccess

4.86 out of 5 average rating, 69 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 spacesParking

Private, pet-friendly home rentals

Cottage in Chappaquiddick

A cozy living area features a lightweight sofa adorned with colorful cushions, complemented by a pink upholstered chair. Large windows reveal ocean views, allowing natural light to fill the space. A small table holds fruit and a book, creating a welcoming setting.

5.0 out of 5 average rating, 35 reviews

Beachfront Cottage + Studio w. Town Access

Outdoor spacesWalkabilityView

4.9 out of 5 average rating, 39 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

PetsWalkabilityLayout

Vacation home in Edgartown

The exterior of a two-story house is highlighted by a wooden staircase leading to the front door. Vibrant blooming flowers frame the house, enhancing the natural surroundings. Lush green grass and trees add to the serene ambiance of the location.

5.0 out of 5 average rating, 22 reviews

Beautiful Martha's Vineyard Home

Outdoor spacesComfortDecor

4.94 out of 5 average rating, 32 reviews

A bright sleeping area features a spacious bed with white linens and two accent pillows. A small round table and two chairs are positioned near a sliding glass door, which offers a view of the outdoors. Natural light enhances the warm tones of the wooden floor.

Apartment in Oak Bluffs

Single Occupancy Oak Bluffs Studio Apartment

WalkabilityPetsNearby

4.85 out of 5 average rating, 27 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

Outdoor spacesPetsAccuracy

4.98 out of 5 average rating, 50 reviews

An outdoor deck with a wooden dining table and matching chairs is shown, illuminated by a vibrant sunset. Lush greenery and the neighboring buildings can be seen in the background, creating a peaceful setting for dining al fresco.

Home in Chilmark

Fun, Authentic, Waterfront Cottage/air conditioned

Outdoor spacesPetsBiking

A two-story home with a classic design is set amidst lush green grass, surrounded by trees. A welcoming porch with rocking chairs is visible, providing a relaxed outdoor space. The gravel path leads to the front door, enhancing the inviting appearance of the entrance.

4.87 out of 5 average rating, 55 reviews

West Tisbury Privacy! Lambert’s Cove Beach Access.

Outdoor spacesPetsIndoor spaces