Vacation rentals in Oak Bluffs

4.92 out of 5 average rating, 110 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?

Guest suite in Oak Bluffs

An aerial view highlights a shoreline featuring sandy beaches and a long wooden pier extending into calm blue waters. Surrounding the area are residential homes and green landscapes, with boats visible on the water. The clear sky and vibrant hues create a scenic coastal environment.

4.99 out of 5 average rating, 113 reviews

Sea View Waterfront Beachfront Apartment

Prime location- right across the street from a sandy beach, a few minutes walk to the harbor, downtown, and transportation (boat, bus, etc). This beautiful street-level one-bedroom apartment sits across the street from the ocean, where you can take a dip and enjoy the beach. The apartment was recently redone and has a small bedroom with a queen size bed, small bathroom, full kitchen, and living room area with pull-out couch. Convenient to take the ferry into Oak Bluffs and walk to the apartment

Guest suite in Oak Bluffs

A sliding barn door crafted from light-colored planks is viewed against a textured wood wall. The door features a black handle and a metal track, providing a modern touch. Nearby, a diamond-shaped mirror is mounted, adding visual interest to the room.

4.95 out of 5 average rating, 362 reviews

Lovely 2 BR Oak Bluffs Apartment

This 100% private apartment is on the first floor of a shared house where owners and their son live upstairs. There are no shared spaces. You have a private entrance and parking. The living room, bedrooms, bathroom, and kitchenette are bright and clean. It is exactly 1 mile from Oak Bluffs Center, a half mile from The Cottages and Farm Neck Golf Course, and a block from Tradewinds walking trails. Across the street is the bike path, & the bus stop is on the corner for easy island transportation!

4.93 out of 5 average rating, 124 reviews

A spacious backyard is visible, featuring a vegetable garden with grapevines climbing along the wooden porch. Nearby, a pile of firewood is stacked, and a garden bed is outlined, with lush greenery surrounding the area. The setting is quiet and peaceful, ideal for relaxation.

Apartment in Tisbury

Harbor view apartment, a quick walk from the ferry

This is a great one bedroom apartment on the second floor of a house. My place is close to the beach, public transport, the Steamship Authority ferry, Black Dog Tavern, Main Street Vineyard Haven, Stop & Shop grocery, and lots of great shopping. You’ll love the convenience! Walk to the apartment right off the ferry boat. Lots to do in walking distance, and onsite parking. The Martha's Vineyard Museum is a 5 minute walk, down the same street. My place is great for couples and solo adventurers.

4.98 out of 5 average rating, 205 reviews

A wooden deck is visible, showcasing a simple bench and a couple of potted plants. Lush green grass and a variety of trees and flowering bushes create a serene garden setting, inviting quiet moments outdoors. Light filters through the greenery, enhancing the peaceful atmosphere.

Apartment in Oak Bluffs

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.

4.92 out of 5 average rating, 170 reviews

The image features a close-up of a front porch with white rocking chairs positioned on a blue painted railing. Lush greenery and vibrant flowers create a peaceful outdoor setting, while blurred colorful houses are visible in the background.

Home in Oak Bluffs

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

4.98 out of 5 average rating, 342 reviews

A wooden deck is shown with outdoor seating, including a table and chairs. Surrounding the deck are blooming rose bushes and lavender plants, adding vibrant colours to the natural landscape. The space is bordered by natural stone and pebbles, leading into a wooded area.

Cottage in Tisbury

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.

4.97 out of 5 average rating, 239 reviews

An open kitchen area is showcased, featuring a central island with two wooden stools. Modern appliances are integrated, complemented by warm wood cabinetry and natural light streaming through nearby windows. A cozy rug lies on the wooden floor, enhancing the inviting environment.

Home in Oak Bluffs

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!

4.91 out of 5 average rating, 254 reviews

Home in Oak Bluffs

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!

4.97 out of 5 average rating, 133 reviews

A charming outdoor pathway lined with vibrant flowers and greenery is shown, leading towards a white door nestled between two cottages. The clear blue sky enhances the inviting atmosphere of the landscaped area, creating a welcoming approach to the properties.

Cottage in Oak Bluffs

Beautiful and walk to everything Oak Bluffs!

This is a beautiful and brand new 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.

Guest suite in Oak Bluffs

A well-lit staircase is visible, featuring beige carpeting with a subtle striped pattern. A wooden handrail runs along one side, leading upwards. At the top of the stairs, a framed picture is mounted on the wall, adding a touch of decoration to the space.

4.99 out of 5 average rating, 167 reviews

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.

4.88 out of 5 average rating, 153 reviews

A clear view of the waterfront showcases various boats anchored in the harbor. Lush greenery lines the background, complementing blue skies and calm waters. Decorative architectural elements are visible on the building's overhang, adding a charming detail to the scenic vista.

Apartment in Oak Bluffs

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)

Vacation rentals for every style

Get the amount of space that is right for you

Houses

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Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Oak Bluffs vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

House rentals in Oak Bluffs

4.96 out of 5 average rating, 72 reviews

The exterior of a newly constructed home is presented, featuring a sloped roof and two skylights. A welcoming porch extends across the front, lined with decorative lighting. Green shrubs and a gravel driveway lead up to the entrance, surrounded by trees that enhance the private setting.

Home in Edgartown

Newly constructed home with AC , new furniture.

4.88 out of 5 average rating, 135 reviews

The exterior of the home is presented at dusk, featuring soft outdoor lighting and classic blue siding. A pathway of stone leads to the entrance, flanked by neatly manicured shrubs and a lawn. A small porch area and steps provide access to the front door.

Home in Marstons Mills

The Mills Retreat- 3BR/2Bath - Beach pass included

5 out of 5 average rating, 37 reviews

A well-maintained exterior of a two-story home is surrounded by lush greenery and a manicured lawn. A gravel pathway leads to the entrance, flanked by flowering bushes, while large windows invite natural light into the living spaces.

Home in East Falmouth

Spacious and immaculate custom home.

5 out of 5 average rating, 60 reviews

A spacious home is set against a backdrop of lush trees, showcasing a unique architectural design with a multi-level roof. A wrap-around deck is visible, enhancing the outdoor space surrounded by greenery and landscaped gardens.

Home in Vineyard Haven

Well-Appointed 3 Bedrm 4 Bathrm w/ 50+ 5* Reviews

4.79 out of 5 average rating, 29 reviews

The exterior of the home is shown, featuring a spacious deck with seating overlooking a large, grassy backyard. The landscape is bordered by trees, with a fenced area visible in the background. A storage shed is located to the left in the distance.

Home in Sandwich

Holiday in the sun!

4.96 out of 5 average rating, 155 reviews

A charming Cape Cod house is set on a secluded lot surrounded by greenery. A paved gravel path leads to the entrance, lined with colorful blooming shrubs. The exterior features a light-colored siding and a welcoming front door, complemented by the natural landscape.

Home in Marstons Mills

Classic Shingled Cape House Wooded Retreat

4.93 out of 5 average rating, 70 reviews

The exterior of the home features a blend of modern architectural styles with traditional elements. A welcoming entrance door is framed by well-maintained gardens, and the private, landscaped yard is enclosed by a white fence. A Belgian block driveway provides ample parking space.

Home in Tisbury

Classic Downtown Property

4.93 out of 5 average rating, 122 reviews

The open living space features comfortable leather seating, a coffee table, and decorative pillows. A ceiling fan provides airflow, while natural light enters through large windows. The kitchen and dining area are visible in the background, showcasing a well-equipped space with modern appliances.

Home in Teaticket

Cute Single Family Home in Nice Neighborhood

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Cottage rentals in Oak Bluffs

4.86 out of 5 average rating, 107 reviews

An outdoor deck is visible, featuring comfortably cushioned rocking chairs facing a serene lake. Lush greenery surrounds the area, enhancing the natural ambiance and offering views of the water under clear skies.

Cottage in Falmouth

Spectacular Beach- front home, includes linen

4.95 out of 5 average rating, 134 reviews

A serene waterfront scene is displayed with calm waters reflecting a clear blue sky. Green grasses and scattered stones line the shore, while small boats can be seen floating in the distance. The tranquility of nature is captured in this peaceful setting.

Cottage in Fairhaven

Seaside cottage

4.9 out of 5 average rating, 39 reviews

A glass bottle filled with various seashells is presented, secured with a rope around the neck. The bottle is positioned on a red fabric surface, allowing light to filter through, adding a soft glow to the arrangement.

Cottage in Fairhaven

Seaside Cottage - Steps to Beach/Close to ferry

4.91 out of 5 average rating, 164 reviews

Cottage in New Seabury

Quaint Cape Cod Cottage on a Private Beach!

4.94 out of 5 average rating, 170 reviews

A bright bedroom features a spacious bed with white linens and decorative pillows. Large glass doors open to a view of the waterfront yard. Natural light floods the room, complemented by blue curtains and wooden beams on the ceiling. A dresser and laundry basket are positioned nearby.

Cottage in East Falmouth

“Cozy Cottage” on Great Bay

4.88 out of 5 average rating, 135 reviews

A serene porch area is framed by lush greenery, featuring white wicker furniture positioned thoughtfully on wooden decking. The entrance is enhanced by a covered awning, offering a shaded retreat surrounded by well-maintained garden plants, including hostas and flowering bushes.

Cottage in Barnstable

Osterville Charming Cottage in the Heart of Wianno

4.81 out of 5 average rating, 113 reviews

An aerial view of a tranquil bay reveals sandy shores lined with small boats gently anchored. The expansive green landscape surrounds the water, while a winding road curves along the coastline, leading to serene beach areas and residential homes nestled among the trees.

Cottage in Pocasset

* Rustic Cape Cod Captain's Quarters Cottage

4.95 out of 5 average rating, 227 reviews

Cottage in Sandwich

WOW VIEW! Waterfront w/ Private Beach, King Bed!

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Condo rentals in Oak Bluffs

An aerial view captures the oceanfront scene, showcasing a sandy beach next to a waterfront building. The tranquil blue waters stretch towards the horizon, and nearby houses are visible along the coastal road, adding to the serene setting.

Condo in Falmouth

1 Bedroom Beachfront Falmouth Condo

4.98 out of 5 average rating, 50 reviews

A modern kitchen features sleek white cabinetry and a spacious countertop. Natural light fills the area through a window, highlighting a gas stove and stainless steel appliances. A small door leads outside, while a patterned rug adds warmth to the floor.

Condo in Tisbury

Short Walk into Town - Nice Comfortable Reasonable

5 out of 5 average rating, 21 reviews

A stone walkway leads through a lush green lawn, flanked by vibrant shrubs and flowers. Two pink chairs are positioned beside a small table, providing a cozy seating area. In the background, charming cottage-style buildings are visible, surrounded by well-maintained landscaping.

Condo in Vineyard Haven

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

4.92 out of 5 average rating, 48 reviews

A screened-in porch features a glass table surrounded by comfortable seating. Natural light filters through the windows, illuminating the space. The backdrop includes lush greenery, enhancing the tranquil outdoor setting.

Condo in Tisbury

Private 3bdrm Condo Tashmoo Woods

5 out of 5 average rating, 3 reviews

Condo in Mashpee

1BR Condo w/ Balcony in Mashpee, MA

4.9 out of 5 average rating, 72 reviews

An outdoor deck reveals a glass table surrounded by six chairs, offering a place for dining or relaxation. A potted plant decorates the center of the table. A view of greenery and nearby homes is visible in the background, along with glimpses of the harbor.

Condo in Tisbury

Sunny 2bedroom condo w pool, walk to town

4.96 out of 5 average rating, 27 reviews

A light blue condominium building stands prominently along a paved road leading to the shoreline. The ocean is visible in the background, with a sandy beach accessible via a pathway. A clear blue sky enhances the serene coastal atmosphere.

Condo in Oak Bluffs

LOCATION LOCATION!! Ocean- View TOP Floor Condo