Martha’s Vineyard is a hidden paradise snuggled on the Atlantic shores south of Cape Cod. This summer colony takes pride in its white-sand beaches and adorable gingerbread cottages. Aside from sunbathing, there are a plethora of outdoor activities to enjoy here. Climb the five charming lighthouses to take snaps or watch stunning sunsets over the coast. Children will be delighted to ride the antique Flying Horses Carousel in Oak Bluffs. To better understand the island’s heritage and history, visit Martha’s Vineyard Museum. Upgrade your stay at this splendid island with an additional comfort of an exclusive pool. Continue reading for a list of the best vacation rentals with private pool in Martha’s Vineyard, Massachusetts.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 12, 2024.
1. The Felicity (from USD 1200)
The Felicity boasts many entertainment areas to better your stay. The large kitchen island serves as a three-seater breakfast bar to have your morning coffee at. Here, guests have access to a game room with pool and hockey tables. The spacious dining area can fit 10 guests for a sumptuous lunch or dinner.
This modern farmhouse features a landscaped backyard with a private pool and plenty of seating. The pool area is surrounded by lush greenery, perfect for a relaxing nature retreat.
Top guest reviews
Amenities & Room:
it is very spacious and we especially enjoyed the pretty patio updated bathrooms and kitchen/family roomsthe beautiful house was spotless comfortable and full of useful amenities at our disposalthe adults enjoyed the extremely comfortable living room and family room areasthe pool was a great touchCleanliness:
it was clean updated and beautifully decoratedwe really enjoyed staying in this home it was very clean and invitingHost:
the host was very friendly and responsiveRead more reviewsLocation:
really enjoyed our stay and perfect location near the shops
2. Iconic mid-century-style home (from USD 882)
This iconic home with shiny wooden interiors can sleep eight guests. The open-concept living and dining hall features floor-to-ceiling glass windows, allowing in natural light and offering easy access to lush views. Sliding doors lead to the spacious balcony, providing even grander nature views.
This accommodation is five minutes away from Menemsha Beach and three minutes to Lucy Vincent Beach. However, if you prefer an intimate dip, a splendid fenced private pool awaits on this property. The pool area is equipped with sun loungers for sunbathing.
Top guest reviews
Amenities & Room:
it is great to have a total of 4 twin beds (and 2 masters) for familieswe enjoyed the open space the pool and the separate sleeping quarters for our teensCleanliness:
place felt relatively clean upon arrivalit was as-advertised clean and with great amenitiesRead more reviewsLocation:
just a wonderful place
3. Family home in a quiet neighborhood (from USD 2363)
This seven-bedroom family home is set in a quiet and private Oak Bluffs neighborhood but is close enough to the town center and ocean. Spend quality time with your family in the game room fitted with a large flat-screen TV, pull-out loungers, and X-box and Playstation game systems. The expansive, fully fenced yard is a dream playground for your pets.
The backyard is curated with a bluestone patio and a private heated pool connected to the outdoor fire pit and grill area. This family home can host a maximum of 16 guests.
Top guest reviews
Amenities & Room:
the heated pool was a real treat for the kids while the adults watched from the hottubthe beds were plush and extremely comfortablethe heated pool at this time of the year was a real delightthe backyard is amazing and we spent lots of time in the heated pool and hottubthe pool hot tub fire pit grill and landscaping were perfectCleanliness:
a beautiful home that was strikingly clean and pristinethe house is very clean and well equippedthe house was super clean with fresh bedding and fluffy white towelsthe house is very clean and well- maintained and the landscaping is immaculatethe property was exceptionally clean and the gardens and outdoor plantings were gorgeousHost:
she answered to our questions patiently and was very helpfulgracie is an amazing hostthe owner went out of her way to make sure the house was perfectgrace the owner was there to greet usabsolutely fantastic and friendly ownerRead more reviewsLocation:
the location was perfectwe loved how close we were to the beach and downtownthe house is very beautiful locate din very quiet neighborhood but not too far from downtownbeautifully maintained vacation rental grace pays very close attention to detailwe could enjoy our time at the house and explore every corner of the island
4. Luxury rental in Katama with amazing views (from USD 1000)
This Katama rental is surrounded by lush greenery and offers amazing views of Herring Creek Farm and South Beach. 10 people can occupy this place. One of the impressive facilities of the property is the spacious mahogany deck with a seating area. It is an idyllic spot to savor the scenic nature views.
A private pool area outfitted by a bluestone patio invites you for a relaxing dip after a long day. For guests who love some fun pool time, there is a water basketball net by the pool! Chaises, tables, and umbrellas are provided for resting in between laps.
Top guest reviews
Amenities & Room:
furniture is incredibly comfortable and good for active families and beach lifestyleenclosed backyard with a heated pool was great toothe other bedrooms on the ground floor have a stunning view overlooking the pool areathe beds are very very comfortable and the air-conditioning is a welcome plusthe deck and heated pool are perfect and where we end up spending most of our timeCleanliness:
fantastic house - very clean and well-maintainedvery clean and very well furnished in all waysthe beds were luxurious and the home was impeccably cleanthe home is exceptionally well kept and very cleanthe house is clean i mean clean the furnishings are new not shabbyHost:
the owner and the caretaker were superthe owner was very responsive and accommodatingthe hosts are super responsive and helpfulowner truly cares about the home and his tennents satisfactionthe owner and caretaker were great to deal withRead more reviewsLocation:
the location is idealthe location was perfectthe location was truly perfect for what we wanted from our tripperfect for a bike ride into town and a 10 minute walk to best beachthe location is fantastic in that it is close to the bike path beach edgartown and public transportation
5. Beach house with extensive outdoor space (from USD 2786)
This six-bedroom beach house for twelve prides itself on attractive features that will delight guests. The third floor of this three-level house is reachable via an adorable spiral staircase. This unique access leads you to a cozy sitting area with windows and a private balcony. This spot is perfect for reading books and spending alone time. The home is outfitted with skylights providing additional charm.
One of the property’s outstanding facilities is the fully fenced pool area with beach loungers and umbrellas for exclusive use. After swimming, hang out with your family at the pool house furnished with a flat-screen TV and comfortable couches.
Top guest reviews
Amenities & Room:
we had a great time with the heated pool grill and hot tubour entire family enjoyed every minute we found the kitchen well stocked and the furnishings very comfortableadults loved the hot tub wine fridge tasteful beach house decor lovely lounge chairs by the poolwe were a diverse group including two kids and the heated pool was a huge plusthis luxury rental property was perfect especially in september with a heated pool and jacuzziCleanliness:
the property was clean and well maintainedthe house was clean and well appointedit's clean updated and well-maintainedthe house was open clean and exceptionally comfortablethe house was great - it was huge clean and very well stocked with towels kitchenware outdoor equipment etcHost:
additionally the property manager was very responsivesteve is a great attentive owner - responds to questions immediatelycaretaker and pool and jacuzzi maintenance was excellentsteve and caretaker craig were always there to make sure our stay was seamlessthe owner steve was wonderful to work with and very accommodatingRead more reviewsLocation:
the location is excellent being close to the beach and within easy biking/driving distance of edgartownwe loved being so close to the beach and the bike pathlocation and privacy were appreciatedit's in a great location and offers lots of privacythe location is great because we could walk to edgartown or south beach
6. Holiday home with office space (from USD 1375)
Suitable for 11 people, this vacation home has everything you need for an upgraded stay. A designated office is available, ideal for work-from-home set-ups so you can accomplish your tasks without missing out on family holidays. Light the fireplace to set the mood and get some work done in time.
Tucked away in the backyard is a heated private swimming pool surrounded by lush green trees. Have your lunch in the outdoor dining area with a sun shed while looking over the beautiful pool.
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
7. Contemporary home for eight (from USD 1200)
This four-bedroom property can accommodate eight guests. Guests have access to a media room with a flat-screen TV and a sofa bed, best for movie nights. A complimentary breakfast is provided here.
An incredible private pool peacefully sits on a sweeping lawn at the rear of the house. Adjacent to the pool is a pool cabana to shelter you from the sun. Get the chance to watch pretty sunsets and purple skies from here.
Top guest reviews
Host:
ginger is a wonderful host and zach as property manager was greatginger is a great host as wellthey are both very responsive and helpfulvery easy to communicate with and helpfulRead more reviewsLocation:
amazing location beautiful beaches in walking distance
8. Bright and sunny single-level property (from USD 1450)
This single-level home features expansive glass windows and is perfect for a group of eight. Relish your lunch or supper in the sun-lit dining room overlooking the elegant spa pool. A little walk around the area will take you to the nearby fishing village and market.
Spend some quality time with your family while playing under the sun in the 4-feet-deep (1.2-meter) private pool. An outdoor shower with hot and cold water is available after a swim. The yard and the pool are fenced so you can swim in privacy.
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
9. The Park Estate (from USD 10000)
This spacious six-bedroom estate features plenty of outdoor space. It is conveniently located just a short drive to beaches, restaurants, ferries, and art galleries. Island Alpaca Farm is within walking distance.
The property is highlighted by an elegant heated pool sitting across extensive pastoral land. The surrounding pool deck is equipped with sun loungers, sun umbrellas, and outdoor furniture. For guests’ convenience, beach towels are also provided. It is important to note, however, that the pool is closed during winter.
Top guest reviews
Host:
claire was responsive and easy to work withthe property is amazing and the host is perfectclaire the caretaker was tremendously kind and helpful and made our stay seamlessRead more reviewsLocation:
rebecca's place was a wonderful get away for our family
10. Tastefully decorated private retreat (from USD 607)
This is an ideal base to commune with nature without parting with modern comforts. This private retreat comes with three bedrooms and sleeps six guests. Perfect for art lovers, this home is tastefully decorated with European antiques and original artwork.
Upon booking, guests are granted exclusive access to a spectacular private pool. Beach chairs and an outdoor dining area are right beside the pool. The screened porch is an excellent spot to meditate while looking over the pool. The frog pond provides an additional charm to the place.
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
Brave the treacherous tides
Stunning beaches are among this coastal island’s honors. Brave the treacherous tides for a swim or surf. After riding the waves, calm your spirits in the comforts of your own pool. For your convenience, we have carefully selected and put up a list of the best vacation rentals with private pool in Martha’s Vineyard, Massachusetts.
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