Vacation rentals with beach access in Oak Bluffs

4.92 out of 5 average rating, 123 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 West Tisbury

The main sleeping area features a spacious wooden bed with grey linens and two light blue towels neatly arranged on the bed. Two bedside tables with lamps flank the bed, and large windows with black shades provide a view of the greenery outside.

4.92 out of 5 average rating, 152 reviews

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

The exterior of a charming house is shown, featuring a gray shingle facade and a welcoming covered porch. Lush greenery and ornamental shrubs frame the entrance, while a gravel driveway leads up to the front door, creating an inviting approach.

4.93 out of 5 average rating, 207 reviews

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, ENDS 9/1) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

4.98 out of 5 average rating, 223 reviews

An open studio space features a cozy sleeping area with a spacious bed covered in light bedding. A soft armchair and a wooden bench provide additional seating. Natural light streams in from a window, enhancing the room's bright atmosphere. Shelving displays books and decorative items.

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.

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.

4.91 out of 5 average rating, 196 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

4.83 out of 5 average rating, 210 reviews

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.

Home in Eastville

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!

5 out of 5 average rating, 106 reviews

A sandy beach stretches along the shoreline, meeting the calm blue waters. People are seen enjoying the sun and swimming. Beach umbrellas and some distant structures are visible under a clear sky with a few clouds.

Guest suite in Falmouth

Location Location Location! Beach, Bike, Ferry

STEPS to beach, bike path, trails, restaurants, shopping, bus to MV Ferry Gorgeous studio/in law apartment, private entry, own parking + patio Open plan living/sleeping area + en suite bathroom Queen bed + queen sleeper sofa: sleeps max 4 Fresh linens, towels, personal care products, first aid, hairdryer, iron Mini kitchen w fridge, air fryer, microwave, toaster oven, dishwasher, cutlery, crockery, coffee maker Our famous home baked goodies! Coffee/tea/milk/sparkling water provided

The front exterior of the house is shown surrounded by lush greenery, featuring a well-maintained lawn. A pathway leads to the entrance, and the porch offers seating. Two sun loungers are positioned on the grass, inviting relaxation in the open space.

4.91 out of 5 average rating, 129 reviews

** 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.

The exterior of a charming two-story house is shown, featuring a wrap-around porch with multiple seating options. The porch is adorned with wooden chairs, and the front yard is grassy, providing ample space for outdoor relaxation. Large windows reflect natural light, contributing to the inviting ambiance.

4.81 out of 5 average rating, 121 reviews

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!

5 out of 5 average rating, 118 reviews

A private garden patio is showcased, featuring a circular table surrounded by four chairs. Plush cushions in vibrant blue patterns adorn the seating. Nearby, two wooden lounge chairs offer additional relaxation options. Lush greenery and flowers provide a natural backdrop, enhancing the outdoor ambiance.

Apartment in Edgartown

Stylish retreat | walk to town | fire pit

* Private garden patio: table & chairs, propane grill, propane fire pit & enclosed outdoor shower * 10 min walk to Edgartown's dining & boutiques * Cable TV, Streaming services, Sonos * High-speed WiFi, comfortable workspace in the bedroom * USB charging ports in the BR & LR * Small but mighty fully stocked kitchen for home-cooked meals * Organic, local bath products * Board games & a small library * HW floors, SS Bosch appliances, DW, W/D, HVAC

Guest suite in West Falmouth

A cozy living area features a comfortable gray sofa with decorative pillows and a wooden coffee table. Natural light fills the space, highlighting a dining table with four chairs. A doorway leads to the kitchen, while a wall-mounted TV provides entertainment options.

4.99 out of 5 average rating, 189 reviews

The Sea-Cret Garden, Guest Apartment

Kick back and relax in this calm, stylish space! This comfortable and peaceful guest apartment is situated in an ideal location in a quiet, beautiful neighborhood that is close to beaches and a short drive to downtown. Take a quick stroll to the West Falmouth Market or the Shining Sea Bike Path. With easy access to Chapoquoit & Old Silver Beach, this perfectly situated apartment is in an ideal spot for your next Falmouth getaway!

Guest suite in West Falmouth

A serene view of a spacious home set against a backdrop of lush greenery and wildflowers. The house presents an inviting facade with multiple windows, surrounded by the natural beauty of the landscape, creating a sense of tranquility.

4.99 out of 5 average rating, 211 reviews

The Ideal Spot

The perfect getaway in Falmouth for all seasons! Our home is beautifully located overlooking Bourne’s Farm and we are steps away to the picturesque Shining Sea Bike Path. Enjoy a beautiful scenic 8.5 mile ride winding your way thru the Sippewisset marsh and along the coastline to the seaside village of Woods Hole. Where you can enjoy the local restaurants ,shops and science learning or jump on the ferry to Marta’s Vineyard.

Popular amenities for Oak Bluffs beach access rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

Apartment in East Falmouth

A functional kitchen space is equipped with essential appliances, including a stove, microwave, and toaster. Wooden cabinetry houses various kitchenware. The layout features a countertop with a dish rack and a small step stool beneath. Soft lighting creates a welcoming atmosphere.

4.95 out of 5 average rating, 331 reviews

In-law apt. with all the amenities of Home.

5 out of 5 average rating, 22 reviews

A sleeping area features a king size bed with a geometric patterned duvet, complemented by a daybed dressed in navy and white stripes. Two bedside lamps provide soft lighting, and large windows allow natural light to brighten the space.

Apartment in Falmouth

Shining Sea-Weekender-On the Bike Path

Apartment in West Falmouth

A charming lower-level apartment is seen beside a garage adorned with solar panels. The exterior features a gravel driveway leading to a welcoming entrance with a set of stairs. Lush greenery and garden plants surround the property, creating a serene outdoor environment.

4.89 out of 5 average rating, 28 reviews

Cozy apartment-access private beach

4.79 out of 5 average rating, 216 reviews

The private deck features a wooden surface surrounded by lush greenery. A small round table with four chairs and a grill are visible, along with a ceramic pot containing a plant. A lounge chair sits on an area rug with a geometric pattern, enhancing the outdoor space.

Apartment in Oak Bluffs

Sunny Private studio amazing deck kayaks & kitchen

4.71 out of 5 average rating, 28 reviews

An outdoor patio area is surrounded by lush gardens featuring blooming flowers and greenery. Two blue chairs are positioned near a table underneath a large umbrella, providing a shaded space for relaxation. The backdrop includes a well-maintained building with multiple glass doors.

Apartment in Aquinnah

Quiet & Serene in Aquinnah

Apartment in West Tisbury

A set of white-railed stairs leads up from a gravel path to the elevated deck. Lush greenery surrounds the base steps, with a glimpse of outdoor furniture visible above. The setting is well-lit by natural sunlight filtering through the trees.

4.73 out of 5 average rating, 11 reviews

Bright loft apartment COMES WITH FREE USE OF CAR!!

A comfortable living area is bathed in soft evening light from large windows, which frame a view of the sea and sunset. Two sofas are arranged around a round coffee table, with lamps providing additional illumination. A television is mounted on the wall.

Apartment in Chilmark

The Mainstay at Menemsha Inn

Apartment in Vineyard Haven

A modern open-plan living space is displayed, featuring a fully equipped kitchen with stainless steel appliances and a large granite island. A cozy seating area with neutral-toned furniture is illuminated by natural light from multiple windows, creating a bright and inviting atmosphere.

5 out of 5 average rating, 68 reviews

Walking-distance to town, shops & ferry

House rentals with beach access

5 out of 5 average rating, 6 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

4.97 out of 5 average rating, 151 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

4.89 out of 5 average rating, 36 reviews

A charming young Victorian home is framed by lush green lawns and neatly trimmed bushes. A welcoming front porch is adorned with pillars and steps leading to the main entrance. The light-colored exterior contrasts gently with the natural surroundings.

Home in East Chop

The quintessential MV home. Now booking for 2025!

5 out of 5 average rating, 7 reviews

An aerial view captures the cozy beach cottage surrounded by lush greenery, with a well-maintained lawn and a stone pathway leading to a seating area. The cottage is positioned close to the water, highlighting its tranquil seaside location.

Home in Tisbury

The Lobster Pot: Lake Tashmoo, beachfront

5 out of 5 average rating, 19 reviews

A modern home with light grey siding is featured in the background, surrounded by landscaped gardens. A heated saltwater pool, with clear blue water, is framed by grey stone paving. Lounge chairs and shaded seating are situated beside the pool, enhancing the outdoor space.

Home in Popponesset

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

5 out of 5 average rating, 66 reviews

A modern house with a unique architectural design is situated on a sloped lot. Large windows reflect the sunlight, while the driveway leads to the entrance. Surrounding greenery includes low maintenance landscaping and strategic plantings. A rooftop area can be seen atop the structure.

Home in Woods Hole

Modern Marvel in Woods Hole - Walk to town & ferry

An open living area is highlighted by high ceilings and large windows allowing natural light. A comfortable sectional sofa with a blue and white throw sits atop a textured rug. The kitchen area features a white island with seating, connecting to a lofted space above.

4.97 out of 5 average rating, 76 reviews

New Pristine Luxury Home on Martha's Vineyard

5 out of 5 average rating, 37 reviews

A custom-built home features a large front porch bordered by well-maintained greenery. The two-story structure is framed by trees, with expansive windows visible. Water views are apparent in the distance, set against a bright blue sky with soft clouds.

Home in Tisbury

Stunning 4/2.5 Water View, Hot Tub, Dogs ok

Condo rentals with beach access

A serene view of the ocean is framed by white wooden architecture. The calm water reflects a clear blue sky, while a sandy beach lies in the foreground, accompanied by a stone jetty. Benches are positioned along the walkway, inviting relaxation.

5 out of 5 average rating, 28 reviews

FABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach

A covered balcony is seen from the exterior, featuring a small bistro dining set. Adjacent to the balcony, a path leads to the beach, with unobstructed views of the ocean. Lush greenery and white gravel enhance the outdoor setting.

4.9 out of 5 average rating, 21 reviews

Breezy Oak Bluffs Condo - Steps to Inkwell Beach!

4.96 out of 5 average rating, 24 reviews

A spacious pool area is enclosed by a white fence, surrounded by lush greenery. Lounge chairs are positioned around the edge of the inviting water, with trees and houses framing the scene in the background. The sky transitions to soft hues during sunset.

Condo in Vineyard Haven

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

A round black table is positioned between two comfortable chairs adorned with patterned upholstery. Atop the table, a decorative floral arrangement includes blue and white flowers, complemented by greenery. A couple of neatly stacked books are also visible.

4.84 out of 5 average rating, 51 reviews

Serenity on Martha's Vineyard

4.63 out of 5 average rating, 8 reviews

An aerial view captures the resort's layout alongside the coastline. Sandy beach stretches along the water's edge, while the Atlantic Ocean meets a calm bay. Behind the resort, residential areas are interspersed with patches of greenery, illustrating the natural beauty surrounding the location.

Condo in Teaticket

InnSeason Resorts Surfside

4.7 out of 5 average rating, 30 reviews

The entrance of the condominium is shown, featuring a wooden exterior with shingles. A pathway leads to the door, surrounded by neatly trimmed shrubs and grass. Bright sunlight highlights the clear sky and the inviting pathway.

Condo in Falmouth

Condo in Falmouth MA

The exterior of the home features a sloping roof with multiple skylights and is surrounded by well-kept greenery. A paved pathway leads to the main entrance, set against a backdrop of bright blue sky and lush, manicured landscaping.

4.92 out of 5 average rating, 13 reviews

Spectacular Martha's Vineyard Island Home!