Vacation rentals with a pool in Oak Bluffs

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Popular amenities for Oak Bluffs rentals with a pool

House rentals with a pool

Guest favorite
A private backyard features a large swimming pool surrounded by a patio with stone paving. Lush greenery and low shrubs border the area, while a wooden table and chairs are positioned nearby. The house is visible in the background, framed by trees.
Home in Mashpee
4.9 out of 5 average rating, 20 reviews

Beautiful Mashpee Home with Pool

JudyRating, 5 stars8 months ago
The house was beautiful, better than expected! It was very spacious with lovely high ceilings in all the rooms. the bedrooms were all large and delightfully decorated, as were the two sitting rooms. In fact the layout worked really well for our family group: master bedroom with en suite for us grandparents, first floor bedrooms for one couple and their two kids with shared bathroom and extra sitting area with TV, and the garden room -with an enormous bed!- and ensuite bathroom for the other couple. The pool was a very good size with comfortable loungers and the large table on the terrace was perfect for mealtimes. The kitchen was fully equipped and there were an enormous range of dishes and utensils! The various beaches we visited were all within easy reach and Mashpee Commons was only a short drive away with a range of restaurants and shops. Nicole was very responsive and answered our questions quickly. We had a wonderful time and the house exceeded our expectations!
Superhost
A spacious bedroom features large glass sliding doors that provide access to a private deck. The room includes a comfortable bed with light bedding, two bedside lamps, and a desk positioned beside a window, allowing natural light to illuminate the space.
Home in New Seabury
5 out of 5 average rating, 7 reviews

Waterfront Home w/ Dock, Heated Pool, Kayaks & A/C

MadisonRating, 5 stars6 months ago
Prescott’s house is such a relaxing place to stay with a big group. The house has a very pretty view and is very clean and peaceful. We are very grateful for such a nice stay at this beautiful house. The BBQ outside didn’t work great but other than that we had a wonderful time! Thank you Prescott.
Top guest favorite
Home in Sandwich
4.99 out of 5 average rating, 80 reviews

"Cape Escape" luxury home w/pool & beach access.

LaurenRating, 5 stars7 months ago
We stayed at the Cape Escape for 5 nights with 7 adults and two young children, and it was perfect. The setting and location of the house was private and serene. The house was well stocked including plenty of beach towels, chairs, baby gear, coolers, wagons, beach toys and more. We used the provided high chair as well. I especially loved the soaps and lotions and extra bath toiletries which made it feel like a hotel. There were multiple areas where our family could gather and eat. Dinners on the back porch st sunset were the best. We hope to be back next year!!
Guest favorite
The charming exterior of the newly renovated home is highlighted by a sloping roof and a welcoming front door. Framing the entrance are neatly trimmed bushes and a small pathway leading to the door. A garage is located on the side, complemented by grassy green surroundings.
Home in Falmouth
5 out of 5 average rating, 15 reviews

Home in Falmouth ~ 5 min drive to beach

AnnieRating, 5 stars8 months ago
This rental is exactly as described with accurate pictures. It was recently renovated with all new furnishings, new kitchen, appliances and baths. Our family enjoyed the brand new outdoor deck, picnic tables, gas grill, swing and s’mores by the fire pit. Unfortunately it was too chilly to use the pool. The kitchen had all supplies to make a large pasta meal. Our daughter ran the Falmouth Road race and so Sunday was a bit chaotic and the owner gave us flexibility to check out a bit later, which was a huge help!!. A wonderful family vacation!! Highly recommend.
Guest favorite
An outdoor pool area showcases a heated inground pool with clear water, surrounded by a wooden deck. Sun loungers are placed nearby, and patio umbrellas provide shade. Lush greenery and trees line the background, offering a serene environment. A beach ball floats in the water.
Home in New Seabury
5 out of 5 average rating, 18 reviews

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

BryanRating, 5 stars7 months ago
Michael is a great host with a phenomenal property. The house was clean, the amenities are great, the pool was warm (we were there at the end of September when highs were in the mid-60s), kitchen is well equipped, and the location is great. We were a group of 3 families - 6 adults and 5 kids - and the layout of the house is perfect for multiple families. Each floor has its own main bedroom, it's own bathroom, plus ample extra space for a crib, pack n play, mattress, etc. We couldn't have asked for a better setup. Unfortunately for our stay the weather didn't cooperate with nearly non-stop rain, but we still had fun in the house (great spaces for movie watching, games, and ping pong), at the nearby children's museum, the beach, and Mashpee commons. We'll be back for sure!!
Guest favorite
Home in Cotuit
4.94 out of 5 average rating, 18 reviews

ShoestringBayHouse, waterfront & pool in Cotuit

ZackRating, 5 stars6 months ago
Perfect stay - just be sure to bring or order sheets and towels!
Guest favorite
A private yard features a heated in-ground pool surrounded by manicured green grass. Lounge chairs are positioned near the poolside, while flowering shrubs add color to the landscape. A basketball hoop stands nearby, providing a recreational option for guests.
Home in Edgartown
4.91 out of 5 average rating, 47 reviews

Beautiful Edgartown Colonial with heated pool.

JenniferRating, 5 stars7 months ago
This house is literally perfect! It was clean, spacious and well stocked. The house is in a quite neighborhood which made it even more relaxing. The pool exceeded all expectations and I hope to have the opportunity to go back next year!
Superhost
The home's exterior features a spacious deck with a spacious area for outdoor seating. A private, unheated inground pool is visible in the foreground, surrounded by a paved patio. Lush greenery provides privacy, enhancing the tranquil atmosphere.
Home in Falmouth
4.89 out of 5 average rating, 27 reviews

Sippewissett Forest Magic by the Sea

MoeRating, 5 stars8 months ago
We have been going to this area for decades and decided to rent vs other options this year. Place very comfortable, easy access (bad leg) with deck ramp key. Water pressure fab as family actually commented. Would look to do again! Excellent…

Condo rentals with a pool

Guest favorite
A clear, inviting pool is seen with a smooth surface reflecting the sky above. Lounge chairs are arranged neatly around the pool area, with several placed alongside a white picket fence. The tranquil setting is enhanced by distant views of the horizon.
Condo in Vineyard Haven
5 out of 5 average rating, 21 reviews

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

JocelynRating, 5 stars8 months ago
Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.
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.
Condo in Falmouth
4.79 out of 5 average rating, 14 reviews

Falmouth MA, Cape Cod Getaway

AileenRating, 5 stars8 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!
Guest favorite
A clear blue swimming pool is surrounded by lounge chairs positioned for relaxation. Lush greenery provides a natural backdrop, while a shaded area offers protection from the sun. Steps lead from the pool to a nearby structure, adding convenience for guests.
Condo in Tisbury
4.91 out of 5 average rating, 47 reviews

Private 3bdrm Condo Tashmoo Woods

JamikaRating, 5 stars8 months ago
What a relaxing and wonderful stay! Barbara’s place was welcoming and even better than the pictures. The house has everything you need and the addition of the community pool was the cherry on top. The host was extremely responsive and helpful. We look forward to returning to Barbara‘s place the next time my family and I visit MV.
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
5 out of 5 average rating, 4 reviews

Capecation! 3-bedroom condo with heated pool

KarlRating, 5 stars8 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.
Guest favorite
An unheated communal pool is framed by a tan patio and white fencing. Surrounding the pool, blue lounge chairs and umbrellas provide seating options. The two-story building in the background features a deck with stairs leading to the second floor, bordered by green trees.
Condo in Tisbury
4.9 out of 5 average rating, 72 reviews

Sunny 2bedroom condo w pool, walk to town

MicheleRating, 5 stars6 months ago
We were very happy with this comfortable 2 bedroom condo. Very clean and furnished nicely. Easy walk into town for shopping and dining. We had a few questions, which Leah answered quickly and in a friendly manner. Would stay again. Thank you Leah!
Guest favorite
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
4.73 out of 5 average rating, 15 reviews

Condo in Falmouth MA

RoberthRating, 5 stars1 week ago
Wonderfull place very peacefull and quiet . Beautiful lake in the Back as well. Patrick was very quick with his responses.overall great experience
Superhost
A clear swimming pool is surrounded by a fenced area, with a light-colored deck. The two-story building in the background features balconies and outdoor seating. Lush greenery is visible nearby, creating a relaxing environment.
Condo in Tisbury
4.77 out of 5 average rating, 13 reviews

Martha’s Vineyard Condo * Near Ferry

AnthonyRating, 5 stars7 months ago
Great location and a nice quaint spot for one or two ! Great value for the area as well

Quick stats about vacation rentals with a pool in Oak Bluffs

  • Total rentals

    40 properties

  • Nightly prices starting at

    ﺩ.ﺇ477 before taxes and fees

  • Total number of reviews

    750 reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

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