Pristine beaches and spectacular sunsets make Martha’s Vineyard a popular tourist destination. Located off the southeastern coast of Massachusetts, it is an island getaway that boasts stunning lighthouses, harbour towns and delicious seafood. Don’t miss the opportunity to visit Aquinnah Cliffs and hike up the trails along the clay cliffs to reconnect with nature. For more adventures, explore Edgartown Lighthouse, the historic lighthouse with a spiral staircase that leads visitors to the top for awe-inspiring harbour views. Additionally, the isle is famed for its farms, wildlife sanctuaries and parks. After a tiring day, there’s nothing like relaxing in a swimming pool, away from crowds. There are plenty of accommodations with relaxation amenities on this mesmerizing island. Scroll down for the best Airbnbs with pool in Martha’s Vineyard, Massachusetts.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 13, 2024.
1. Spacious residence ideal for families; Oak Bluffs (from USD 640)
Indulge in the lap of luxury at this spacious residence in Oak Bluffs that can accommodate up to 10 guests. The property has a beautiful outdoor pool with a built-in sitting area to enjoy a soak in shallow waters. The heated pool has a water temperature of 28° C (83° F), so guests can swim even on chilly days. Take note that the pool is closed from the start of November until Memorial Day at the end of May.
Additionally, the elegant haven has tastefully decorated bedrooms, a fully equipped kitchen and driveway parking for up to six vehicles.
Top guest reviews
Amenities & Room:
the heated pool was definitely a highlight - we were in it constantlythe space was ample and the place proved to be cozy and comfortableCleanliness:
this is a beautiful home very clean and comfortableit was spacious clean and centrally locatedthe house was awesome we had a blast the pool was in great condition and was very cleanRead more reviewsLocation:
it is in a central location on the island perfect for visiting all the townshipsthis place was in an ideal area in oak bluffs and we would definitely consider renting againit’s located in a quiet cul-de-sac and it was a nice getaway from the citywonderful and spacious home very close to the oak bluffs ferry (and vineyard haven )
2. Modern house near Lucy Vincent Beach; Chilmark (from USD 1450)
Make your vacation epic at this modern beach house with a private outdoor pool in the rural woods of Chilmark. The property has a 1.2-m (4-ft) deep spa pool for a splashing good time outdoors. The pool uses propane for heating, and using it beyond 100 USD per week incurs extra costs. Guests are requested to turn off the heater if it’s not being used.
What makes this property outstanding is the elegantly styled bedrooms, wall-to-ceiling windows that invite natural light in and a spacious living room to lounge with family. Do you love beach adventures? Just 1.6 km (1 mi) from home is the stunning Lucy Vincent Beach for fun-filled days under the sun. Take note that guests will need a beach pass here.
Top guest reviews
Amenities & Room:
lots of space and light the rooms were perfect and the communal areas were greatand no small thing the wifi worked perfectlyvery comfortable house with lovely lightliving room is a particularly stylish space with fresh flowers and good seatingwe enjoyed the pool everyday and having dinner on the deck in the eveningsCleanliness:
it was comfortable very clean and close to the spectacular lucy vincent beachHost:
harriet was a wonderful hostshe was a wonderful host and the house was perfectharriet was an excellent host she was in contact with us to make sure we were comfortableshe is welcoming and warm and extremely responsiveharriet is a great host with wonderful tips and easy communicationRead more reviewsLocation:
the location is excellentthe house is in a great remote location with very good hiking trails a few steps awaylocation was exactly what we needed for a relaxing family vacation close to the most beautiful beachesperfect location for us seeking quiet and easy access to farmstands beach and fishing/seafood of menemshait is located on a private drive in chilmark with two beautiful walks just steps from the door
3. Fully furnished home surrounded by fields; Edgartown (from USD 607)
Escape to a nature’s paradise at this fully furnished home surrounded by green fields in Edgartown. The property has a private pool in the garden with shady trees and a frog pond nearby for outdoor adventures. The pool and pond are fenced, so parents need not worry about their kids’ safety on the premises.
In addition, there are poolside sun loungers to bask in the sunshine, an outdoor shower and complimentary beach towels to dry off after swims. You’ll fall in love with the modern interiors, well-stocked kitchen where you can prepare simple meals and piano for the music lovers in the family.
Top guest reviews
Amenities & Room:
it doesn't have air conditioning but cool enough at night so that it wasn't necessaryloved the open floor plan breezy airy light filled we kitchen and gathering spacethe beds were incredibly comfortableit's peaceful beautiful and the pool was a treat on the hot daysa beautiful frog pond in the yard as well as a poolCleanliness:
very clean and comfortable and the pool was a fantastic amenitysuper clean nicely decorated and well supplied with everything you needsuper clean and on such a beautiful plot of landwhat a great place to relax the house was very spacious quiet and overall wonderfulHost:
carissa was a great host very responsive and made sure our family had a great staycarissa was a great host as wellRead more reviewsLocation:
great location that is close to everythingit's a great location for exploring the islandlovely home in secluded but very centrally located up island locationvery close to the bike path i'm glad i brought my bikevery private good location and very clean
4. Four-bedroom abode with large backyard; Oak Bluffs (from USD 1375)
Water lovers will be delighted to relax by the gorgeous swimming pool in the large backyard of this stylish four-bedroom abode in Oak Bluffs. The private heated pool is 2.4-m (8-ft) deep for guests to enjoy a full-body workout even on cold days. Amp up the fun with pool toys from the pool house.
The property has a spacious deck with comfortable patio furniture for parents to relax while kids splash around in the pool. Spending time outdoors is exciting as there is a new barbecue grill and a fire pit for cookouts under the stars.
Top guest reviews
Amenities & Room:
the pool and backyard were glorious we barely left the houseloved staying at this place large pool fast wifi plenty of places to sleepluckily a few people who were there own pools and started maintaining itthe deck and pool were great for us also and we particularly liked the outdoor speakersCleanliness:
everything was clean and had everything we neededvery spacious and cleanthe house was clean and great for a big group to spend time togethervery clean & has everything you can think ofvery clean and great hostHost:
our host grace was wonderful and accessiblethe host grace was super responsive friendly and helpfulgrace is a wonderful host the house is a perfect place to relax and enjoy time with friendsthe house was adorable and grace was very responsive and helpfulgrace was very responsive and returned our messages and questions promptlyRead more reviewsLocation:
awesome location and amazing pool in backyard plenty of rooms availableit was a great location and perfect size to comfortably sleep 11 of usfantastic private location spacious and extremely comfortable thank you for your hospitality grace
Superhost
5. The Salty Dog; Edgartown (from USD 1100)
If you’re looking for a well-equipped private retreat, then book this holiday home in Edgartown. The Salty Dog is nestled on a tranquil 1 ac (0.4 ha) private land flourishing with verdant greens. If you love spending time outdoors, enjoy relaxing laps in the lovely pool surrounded by flora in the fully fenced backyard. Perfect your tan while reclining on the poolside deck chairs or capture the spectacular sunset by the pool each day.
Accommodation-wise, the property has comfortably furnished bedrooms, nautical-themed decorations and an indoor fireplace to cosy up with loved ones in the living area.
Top guest reviews
Amenities & Room:
the house has lots of space the pool is awesomeamazing backyard with a pool - perfect for the warmer weatherwe had a great time with the pool backyard bbq and other accommodations like gamesthe kitchen and bathrooms are all brand new and the pool is huge and well maintainedHost:
jill is a very responsive and attentive hostjill is a very responsive and attentive hostjil is a super host accomodating and communicative and making sure we felt looked after the entire weekendjill was a responsive and helpful hostjill is an incredibly thoughtful and gracious hostRead more reviewsLocation:
great location just a short drive to edgar town and oaks bluffthe location between edgartown and west tisbury is greather place is the perfect balance of privacy and easy access to the city
6. Stunning retreat by a lagoon; Oak Bluffs (from USD 450)
For a fun-filled vacation in Martha’s Vineyard, consider staying at this gorgeous vacation home in Oak Bluffs. The property is nestled in a peaceful neighbourhood and has a fully fenced backyard with a private pool and landscaped garden. Guests enjoy breathtaking lagoon views and easy pool access as it’s ungated and unlocked. Note that the swimming pool with a spa is heated only during the summer season. Kids shouldn’t be left unattended in the pool area.
Discover more water adventures on the property’s privately owned beach, accessible via steps from the backyard. After a long day, you can retreat to a comfortably furnished abode with a well-equipped kitchen, laundry facilities and air-conditioning.
Top guest reviews
Amenities & Room:
the light filled living room and kitchen are definitely a highlightthe house is amazingly spacious and cozy with the most amazing viewit was very spacious with lots of indoor and outdoor seating and comfortable bedsit has a wonderful location for yard games beautiful pool to enjoy and a spectacular viewmore than enough room for 8 people to spread out and be comfortableCleanliness:
the house is beautiful clean and felt right at homegreat house pictures don't do it justice amazingly clean upon arrivalit’s spacious clean and has every accommodation imaginablethis is a great house: clean great location and with great amenitieshouse was clean with plenty of natural light and plenty of bedrooms/bathroomsHost:
the host was very responsive and helpful with the questionsthe property mgr and the host were very responsive in keeping us updatedthe homeowner (larry) and property manager (mike) were very responsive and accommodatingbeautiful home in a great location quick and easy communication with the owners thanksRead more reviewsLocation:
amazing location and amazing housebeautiful location and stunning housegreat location and beautiful homelocation was perfect for our staygreat place and terrific location
7. Immense residence with well-equipped kitchen; Oak Bluffs (from USD 1571)
Are you planning a holiday getaway in Oak Bluffs with a large group of friends? This immense residence is your best bet. The property has a private heated pool with water temperatures at a comfortable 28° C (82° F) from the start of June to around mid-September. Keep in mind that the pool is closed from mid to late September. The swimming pool is ungated and unlocked, providing easy pool access to guests.
If you love spending time indoors, the property has well-appointed bedrooms, a fully functional kitchen with modern appliances and entertainment options such as game console to keep youngsters occupied.
Top guest reviews
Amenities & Room:
all of the beds were comfortable and had pillows and beddingamazing home the heated pool was a huge bonusCleanliness:
lots of space for large group amazing outdoor fun very clean and good communicationHost:
grace was a wonderful host and very responsive to any questions we hadhost was responsive had great recommendations for food and activities and was overall extremely helpfulshe is also very responsive via texts and phone callsshe is super friendly and showed us the proper way to use the grillpatricia was very helpful from the initial contact and throughout our stayRead more reviewsLocation:
amazing location and great space for large groups
8. Contemporary haven with pool house; Edgartown (from USD 500)
Make yourself at home at this contemporary haven within walking distance to downtown Edgartown. This property has a private saltwater pool that’s ideal for swimmers who are sensitive to chlorinated waters. Take note that the unheated lap pool is available from May to October annually.
Some outstanding features of the house include heated floors in the bathrooms, free driveway parking for up to five vehicles and a private fenced backyard to lounge next to nature. For a quiet escape from life’s distractions, head to the pool house equipped with a comfy futon, a work desk, and a mini fridge for refreshments.
Top guest reviews
Amenities & Room:
beautiful house with lots of room and amenitieslove the heated bathroom floorsairbnb has a nice backside pool and decki especially enjoyed the hot showers and heated floorsthe house was immaculate the beds were comfortable the lounge areas were large and the kitchen/bathrooms were well equippedCleanliness:
the house was clean and well keptthe house was very clean and had everything you could ask for and morethe house was clean and spacious with a well equipped kitchenhouse and pool was cleanhot tub was clean and ready to go when we arrivedHost:
jerry is responsive to questions or issuesthank you jerry you were an excellent hostjerry was extremely helpful and responsive to questions and little things that came upgreat home great location great hostwe truly enjoyed the property and host had set it up exceptionally wellRead more reviewsLocation:
the location was also ideal for usbeautiful house in a great location only a few minutes from edgartown but very privateyou can easily walk or bike to eithergreat location very nice and functional home makes a trip to the vineyard very easythe house is in a perfect location close to south beach and also edgartown
9. Stately colonial house with a ping-pong table; Edgartown (from USD 1550)
Have an enjoyable stay at this stately colonial house in Edgartown with a private in-ground pool in its fully fenced backyard. This outdoor swimming facility is being heated on Memorial Day weekend up to the end of September. There are ample poolside deck chairs to relax under sunny skies by day and go stargazing by night.
The property has elegant interiors, central air-conditioning and a well-stocked kitchen with modern appliances to cook up a storm. There’s also a cosy family room that comes with a ping-pong table. Kayaks and bikes are available, too.
Top guest reviews
Amenities & Room:
the kitchen is great and had all the necessary utilities for cooking any mealswarm pool large yard multiple living areas high speed internet and great tvs and techwe really enjoyed the heated pool toobrand new pool and outdoor lounge space that we enjoyedwe loved the huge family table and the well-stocked kitchenCleanliness:
everything was clean and in working orderhouse is huge and clean and lots of space for everyoneloved this house it was a beautiful quiet neighborhood and a clean updated large housethe home was clean and everything worked as it shouldHost:
sue is a perfect hostsue was very responsive in our correspondence and always quick to answer any questionssue and peter were very helpful and accommodatingthe home is clean well furnished and the owner very responsive to communicationssue is very responsive and helpfulRead more reviewsLocation:
great location but you do need a carperfect place to stay and nice location in a quiet neighborhoodthe edgartown location was a perfect for relaxing in between journeying around the islanda nice time was had by all and the location is greatwe couldn't have asked for a more wonderful place to stay
10. East Chop Waterview Farmhouse; Oak Bluffs
East Chop Waterview Farmhouse is a spacious property fit to accommodate up to 15 guests. Aside from its tastefully furnished bedrooms and roomy interiors, the modern residence has a private dip pool for refreshing swims in the fresh air. You’ll also have access to a private hot tub.
Some stellar amenities include a large, fully equipped kitchen, an indoor gas fireplace to keep the place warm in winter and a huge front porch overlooking the well-manicured yard. What guests loved most was the breathtaking lake views and excellent location close to downtown Oak Bluffs and its attractions.
Oak Bluffs, Massachusetts, United StatesAccommodates: 8
Top guest reviews
Amenities & Room:
dip pool and water views were awesomeHost:
she was responsive and helpfullisa was an absolutely outstanding hostshe was extremely helpful before and during our staylisa’s place is amazing and she is one of the most attentive hosts i’ve ever hadthis property is amazing as is the host lisaRead more reviewsLocation:
excellent home and great locationall in all this is a great place to enjoy your timeall in all a place we would easily come back to if the opportunity arises againwould definitely recommend for anyone looking for a great place to relax on the vineyard
Have an enjoyable vacation in Martha's Vineyard
Martha’s Vineyard has activities aplenty for solo travellers, couples and families. From wilderness wandering to windsurfing, there’s something for everyone. After an exhausting day, you’d love to find a perfect place to relax. Take your pick from this list of the best Airbnbs with pool in Martha’s Vineyard, Massachusetts.
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