Condo vacation rentals in Oak Bluffs

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.

4.96 out of 5 average rating, 27 reviews

LOCATION LOCATION!! Ocean- View TOP Floor Condo

TaylorRating, 5 stars9 months ago

Heather's place is beautiful! An amazing location with close proximity to the OB steamship authority station, a number of bus lines, and the beach! The view and location are unbeatable! Heather was also super responsive in terms of coordinating flexible check-in/check-out times which was very much appreciated. Overall, would definitely recommend to anyone visiting OB :)

Top guest favorite

A cozy entryway is highlighted by a staircase leading to the upper floor. Soft carpeting covers the stairs, and light filters in through a nearby window. A glass vase containing decorative branches is placed beside the stairs, complementing the warm wooden flooring.

Condo in New Seabury

4.98 out of 5 average rating, 139 reviews

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!

BillRating, 5 stars4 days ago

Ethan and Amy’s place was really nice and cozy. The kitchen and living room was beautiful and the rooms had plentiful space. Ethan was very responsive and helpful! Definitely staying here again if I am in the area!

4.9 out of 5 average rating, 73 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 Vineyard Haven

Sunny 2bedroom condo w pool, walk to town

ShayRating, 5 stars7 months ago

We had a great time at Leah’s place. She is a terrific communicator, immediate responses. She also reached out to share about local fun events that were happening during our stay. So nice! We would definitely stay there again.

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

This 3 bedroom (3 king) 2 1/2 baths newly renovated condo is in a private setting with screened in porch. New kitchen, gas grill on deck, outdoor shower. -Access to the Tashmoo Woods Association pool, tennis courts and play ground. -Close to West Chop beaches. -Two miles from downtown Vineyard Haven. On bus route, but best to have a car. -The primary bedroom (king bed) is downstairs and the 2 upstairs bedrooms share a bath (shower only). Minimum rental 5 days, 1 week in summer.

A charming street scene depicts various shops housed in colorful historic buildings. Parked cars line the street, and a large American flag is visible. The evening sky casts a soft light enhancing the inviting atmosphere of the downtown area.

4.79 out of 5 average rating, 14 reviews

Ocean View Gem, Walk to it All, No Car Needed!

Lovely 2 BR/1 BA condo sleeps up to 4 guests. Amazing location with spectacular views! Experience island living at its finest. Martha’s Vineyard vacationers dream! Enjoy walking everywhere: Inkwell Beach, Circuit Avenue, Linda Jeans, OB ferry and harbor, Campground Cottages, Tabernacle, shops, restaurants and more! Have a front seat to Illumination fireworks, spectacular sunrises and romantic sunsets on the private balcony. No car needed; however, parking is available if required.

4.52 out of 5 average rating, 71 reviews

A cozy living area displays a couch with decorative pillows, accompanied by a wooden coffee table. A dining table with several wooden chairs is positioned nearby. The kitchen features light cabinetry and modern appliances, with natural light streaming through multiple windows.

Condo in Barnstable

Oceanside Cottage Apt2 across Craigville Beach

Experience a perfect family retreat at this charming 2-bedroom, 1-bath cottage. Craigville Beach is 200 feet away. Whenever you're not playing the sand, venture and explore any attraction, restaurant, and shop in the Cape, since we are conveniently located in mid Cape We provide all the comforts of home here, including loaded kitchen, AC, WIFI, beach chairs, gas grill, and even beach toys for kids. So just come, enjoy, and relax! It is perfect place for beach lover!

Top guest favorite

Condo in Popponesset

4.94 out of 5 average rating, 72 reviews

Beach Cottage 3nts/4th Free in August,Mashpee MA

Enjoy our 1 br condo with the BEST view of all the condos, steps from Deans Pond! Walk to Popponesset Market Place, Popponesset Inn & Nantucket Sound. Stroll the beach, hike through conservations areas. Visit quaint shops, restaurants, antique stores! Enjoy morning coffee & evening cocktails on our private deck with that Spectacular View! Spa Rain shower bath, chef's kitchen. Egyptian Cotton Sheets!! NO: Pets-Smoking-Vaping-Parties NO Micro Fiber Sheets!

Vacation rentals for every style

Get the amount of space that is right for you

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Convenient locations with everyday essentials

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A space thats all yours, with room for everyone

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Stylish accommodations and amenities

Popular amenities for Oak Bluffs condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

A scenic coastal view is presented, featuring a sandy beach gently sloping towards calm waters. The shoreline is lined with residential properties surrounded by lush greenery, with wide blue skies above and minimal clouds visible.

Condo in Popponesset

4.67 out of 5 average rating, 36 reviews

Coastal Nest at New Seabury

LindaRating, 5 stars8 months ago

Great place and location. Enough space for 4 adults and a small child in the bunk area. Short walk to the marketplace and great spot to cook in and a grill out back.

A serene beach scene features soft, sandy shores leading to calm waters. Smooth stones form a breakwater, creating gentle waves. The sky is clear with scattered clouds, emphasizing the tranquil atmosphere and inviting nature of the shoreline.

RebeccaRating, 5 stars2 weeks ago

Island Inn - Residential Suite - 28G - Oak Bluffs,

This is our third time staying at the Island Inn; each time has been accomodating and exactly what we were looking for in our stay! The hosts are very responsive and the location is excellent. The price of the stay can't be beat! We'll definitely be booking another stay in the future.

A sandy beach extends along the shoreline, leading to a tranquil sea with gentle waves. Large rocks form a jetty, creating a barrier between the beach and the open water. Soft clouds drift across a blue sky, enhancing the serene coastal scene.

Island Inn - Cottage - 21E - Oak Bluffs, MA

A serene beach scene features soft white sand alongside clear blue waters. Large, smooth stones create a jetty extending into the ocean, framed by gentle waves lapping at the shore. A bright sky with scattered clouds complements the tranquil coastal landscape.

Island Inn - One Bedroom Suite - 10C - Oak Bluffs,

A serene beach scene features soft sandy shores meeting calm blue waters. The rocky jetty juts into the ocean, bordered by wispy clouds in a clear blue sky. Gentle waves lap against the shore, creating a tranquil atmosphere.

Island Inn - Residential Suite - 35G - Oak Bluffs,

A serene beach scene is depicted, with gently rolling waves lapping at the sandy shore. Large rocks create a protective barrier along the coastline, while a clear blue sky with scattered clouds stretches overhead, enhancing the tranquil seaside atmosphere.

Island Inn - Residential Suite - 38G - Oak Bluffs,

The exterior of the one-story unit is shown, featuring shingle siding and a covered porch area. Lush green grass surrounds the building, and several seating areas are visible under a shaded tree. The space offers a welcoming atmosphere, perfect for relaxation.

Island Inn - Studio Suite - 23F - Oak Bluffs, MA

A sandy beach is shown leading to calm, turquoise waters. Smooth stones create a barrier at the water's edge, while scattered seaweed adds detail to the shoreline. The sky overhead is bright blue, with soft clouds drifting in the distance.

Island Inn - Residential Suite - 39G - Oak Bluffs,

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Pet-friendly condo rentals

A welcoming living area is presented with warm wooden accents and a cozy fireplace. A comfortable sofa faces a coffee table, while an armchair is positioned nearby. Light filters through sheer curtains, complementing the rustic decor. A TV is mounted above the fireplace.

CCRating, 5 stars1 month ago

Island Inn - Residential Suite - 33G - Dog-friendl

Nice host great stay comfortable place Just had some loud upstairs neighbors at 5am then after 8pm Also you could hear the upstairs folks walking and talking .. not Much installation between the spaces But it was comfortable and close to inkwell

A charming duplex building is showcased, featuring a light grey exterior with blue doors. A large star decoration is mounted above the door, surrounded by vibrant greenery and blooming hydrangeas. A sandy path leads to the entrance, creating an inviting approach.

4.83 out of 5 average rating, 145 reviews

A Perfect. Walk to beach, harbor and Main Street

DavidRating, 5 stars7 months ago

Great location - walkable to downtown Falmouth, many nice trails, and the farmer's market. Long walk or short drive to Woods Hole (for Pie In The Sky and WHOI). Also very close to Windfall Market for some quick and easy food. Great host - Brian was very responsive and clear with instructions. There was a kitchen item missing, and Brian brought a new replacement in a day. The space is slightly cramped - the kitchen and couch and dining table are all in 1 room, so there isn't a much space to hang out as a group.

A cozy living area features a mounted television above an electric fireplace, surrounded by a wall adorned with nautical decor. A glass coffee table sits on a patterned area rug, while high-backed bar stools are positioned at a kitchen counter nearby.

CaitlinRating, 5 stars2 weeks ago

Island Inn - Residential Suite - 31G - Dog-friendl

This place was amazing, it was clean and just a 4 min drive from the ferry and all the shops. Only thing is the internet wasn’t the greatest and I had to use up my hotspot at my cost

An outdoor patio area features a large red umbrella shading a dining table surrounded by six decorative chairs. A gas grill stands nearby, with vibrant flowering shrubs adding a natural touch to the serene environment.

Condo in New Seabury

4.6 out of 5 average rating, 15 reviews

2BR dog-friendly 2-story condo with community pool

MichaelRating, 5 stars6 days ago

Place was immaculate, if I was in the market, I’d definitely consider buying in this community. Although there was only one assigned parking spot, parking was not an issue for our 2nd car.

A charming duplex features a well-maintained exterior with a landscaped yard, showcasing vibrant hydrangeas in various shades. A gravel driveway leads to the entrance, marked by a stone pillar displaying the number 20. The home is set amidst a backdrop of lush greenery.

4.88 out of 5 average rating, 123 reviews

A Spectacular. Walk to beach, town and harbor 20

KatieRating, 5 stars8 months ago

Amazing stay. Didn’t have to get an Uber once, everything was walkable. Brian communicated consistently.

A cozy living area features a comfortable blue sofa adorned with colorful cushions. A light wood coffee table sits on a warm-toned floor, surrounded by a dining table with two chairs. Wall art and a softly glowing lamp enhance the inviting atmosphere.

5 out of 5 average rating, 3 reviews

Island Inn - Residential Suite - 32G - Dog-freindl

RebeccaRating, 5 stars3 weeks ago

The Island Inn was beautiful and they were amazing hosts. Very accommodating.

5 out of 5 average rating, 3 reviews

Island Inn - Two Bedroom Suite - 2A - Dog-freindly

TedRating, 5 stars1 month ago

The studio was very clean and the amenities were good. The location was nice and the surroundings of the property were very nice.

An open living area features a wooden dining table surrounded by four chairs, creating a welcoming space for meals. A well-appointed kitchenette is visible with cabinets and essential appliances. A flat-screen TV is mounted on the wall, enhancing the comfort of the space.

ArthurRating, 5 stars23 months ago

Island Inn - One Bedroom Suite - 8C - Dog-friendly

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Condo rentals with a pool

A large outdoor pool area is surrounded by green trees and blue skies. Comfortable lounge chairs are arranged around the pool, providing space for relaxation. Umbrellas offer shade for guests, and pool users can be seen enjoying the water.

Condo in Mashpee

Beautiful & Spacious Townhouse on CapeCod 7/25-8/1

Andy’s place was a perfect stay for a vacation getaway. He was very responsive, and his unit was true to the pictures. I would highly recommend this home for a future stay.

JaleneRating, 5 stars8 months ago

An inviting outdoor pool area is framed by neatly arranged lounge chairs under vibrant blue umbrellas. Surrounding trees provide shade, enhancing the tranquil setting. The pool invites relaxation and enjoyment, with sunlit water reflecting the clear blue sky.

Condo in Mashpee

2BR Condo in Cape Cod w/ Patio & Laundry

Beautiful stay. It’s a Time Share type place so you have to bring any and all spices and basics like sugar and salt.

An outdoor swimming pool is surrounded by lounge chairs and umbrellas, providing a comfortable space for relaxation. Tall trees and greenery enclose the area, enhancing the tranquil atmosphere. Clear blue skies and well-maintained landscaping contribute to the inviting poolside setting.

4.79 out of 5 average rating, 14 reviews

Falmouth MA, Cape Cod Getaway

AileenRating, 5 stars9 months ago

Very pleasant stay! Nice value, size and layout for our family of 5 (3 young kids). 2nd floor unit, accessible via stairs. Area is quiet and secluded, but very close to everything you would want to do in and around Falmouth (drive times: ~8 mins to downtown area, 7-15 mins to nice beaches, 7-10 mins to parking/shuttle for Martha’s Vineyard ferries, ~20 mins to Woods Hole). Kitchen is well appointed—we cooked half of our week’s meals. Community pool was well maintained, has deep end down to ~8ft and shallow at 3ft, and has ample tables/umbrellas/loungers. Very friendly neighbors and very responsive/gracious hosts. Would stay again!

ChristophRating, 5 stars6 months ago

A serene saltwater pool is surrounded by lounge chairs and umbrellas, set among vibrant greenery. A colorful arrangement of blooming flowers frames the foreground, adding to the tranquil atmosphere of the outdoor area.

Condo in Mashpee

Cape Cod Townhouse w/ Patio & Kitchen

Great place and location!

A clear swimming pool is surrounded by well-maintained grass and tall, green trees. Several lounge chairs are positioned around the pool's perimeter. A colorful float is visible in the water, and a shaded area is indicated by a large umbrella. The overall setting is peaceful and inviting.

4.7 out of 5 average rating, 37 reviews

Lovely lakefront studio/condo with pool

LindaRating, 5 stars9 months ago

Luisa was very responsive to any questions we had. Her place is cute and cozy, very quiet, but everything we wanted to do was close by.

5 out of 5 average rating, 5 reviews

A private heated pool is surrounded by a concrete patio, with shade provided by a large umbrella. A dining table with several chairs is located nearby. Lush greenery and colorful flowers add a vibrant touch to the pool area, creating a relaxing outdoor space.

Condo in New Seabury

Capecation! 3-bedroom condo with heated pool

KarlRating, 5 stars10 months ago

We drove from Maryland up to the Cape, through lots of traffic. The host was great and responsive, suggesting great places for dinner. Our week was just amazing, wish we could have stayed longer. The pool was a perfect way to start and end the days and the bikes were a great way to explore the neighborhood. We really hope to return, just so much more we wanted to do.

A relaxing outdoor pool area features lounge chairs arranged along the pool's edge. The surrounding building, showcasing spacious balconies, houses multiple units. Guests enjoy sunbathing and walking nearby, with clear skies overhead enhancing the scene.