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 stars10 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 deck features a wooden dining table with matching chairs, overlooking a private heated pool and serene water views. Lush greenery surrounds the area, while a private dock is visible along the shoreline.
Home in New Seabury
5 out of 5 average rating, 7 reviews

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

MadisonRating, 5 stars8 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, 83 reviews

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

Kimberly AnnRating, 5 stars5 days ago
I can not say enough about how wonderful this house was to stay at for my son's wedding weekend. This house was very clean and organized. The hosts were extremely thoughtful with how everything was laid out. They thought of everything that you would need or might forget. The outdoor space was great!! My grandchildren and kids floated around the pool and played yard games. I did not hear "I am bored" and that was wonderful. We had so much space to get ready for the wedding and were able to get wonderful pictures of my son getting ready for his wedding. There are so many places in the house to either gather together or to go off and do something else. Two kids were playing chess while the younger ones were down playing with the video games and my dad and the men were watching the Masters. We had plenty of space for everyone to hang out. My entire family enjoyed this house and can't wait to go back.
Superhost
A heated saltwater pool is surrounded by a spacious patio, complemented by comfortable lounge chairs and a beach ball. Lush greenery and a wooden fence provide privacy, while a charming garden shed is visible in the background.
Home in Teaticket
4.83 out of 5 average rating, 6 reviews

Charming Home-Pool, Game Room, walk to quiet beach

TedRating, 5 stars10 months ago
We had a wonderful time at this home. The pool was clean and warm; we used it every day. The house was well stocked- dishes, spices, utensils, pots and pans… and plenty of chairs out by the pool for outdoor meals. The neighborhood was quiet and safe to take nice morning walks down to the little beach 1/4 miles away. Great quality seafood at Falmouth Fish Market, and many grocery/household store options less than 2 miles from the house. We paid extra for the linens; good choice for us since we had a full house.
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 stars10 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…
Guest favorite
The outdoor pool area is surrounded by a black metal fence and features clear blue water. A swan-shaped float is situated on the water, while lounge chairs are positioned nearby. An umbrella provides shade, enhancing the inviting setting.
Home in North Falmouth
5 out of 5 average rating, 16 reviews

New Construction Home with Pool in N. Falmouth

KeriRating, 5 stars1 week ago
We had an amazing stay at Stephanie’s place in Falmouth! The home was immaculate, spotlessly clean and even better than we expected. The photos were beautiful, but somehow the house exceeded them. Stephanie and Ellen were wonderful hosts, very responsive and helpful with anything we needed. The layout was perfect for our family, giving everyone their own private space while still feeling cozy and connected. The pool and hot tub were huge hits and made our time extra relaxing and fun. We would absolutely stay here again. Highly recommend!
Guest favorite
A view from the deck reveals a well-maintained pool area surrounded by lounge chairs and umbrellas. Adjacent to the pool is a tennis court, framed by greenery, providing a serene backdrop. The water sparkles under a clear blue sky, inviting relaxation.
Home in East Falmouth
4.95 out of 5 average rating, 38 reviews

Dog Friendly Cape Oasis | Pool+Beach |Tennis Court

SydneyRating, 5 stars1 week ago
Emily was so kind and responsive and the house was exactly as expected. The walk to the beach was lovely and doable with the toddlers thanks to the wagon provided. It was a quick drive into all things Falmouth and a great home base for us. The stand outs for everyone were how comfy the beds were and we were all obsessed with the outdoor shower. Loved all the thoughtful amenities, such as games and kids dinnerware. Overall very stylish and comfortable. Highly recommend.
Superhost
An outdoor seating area features a round table surrounded by several cushioned chairs on a blue area rug. Green decorative pillows add a pop of color, while trees provide a natural backdrop in a peaceful setting. The railings enhance the open, inviting space.
Home in East Falmouth
4.92 out of 5 average rating, 13 reviews

Jaws House - Great Harbors

MollyroseRating, 5 stars7 months ago
We felt right at home and enjoyed our stay so much! The neighborhood is adorable for walking and our little one loved the playground right down the road. The house is so quiet yet so close to downtown and beaches. Will definitely be back!

Condo rentals with a pool

Guest favorite
An aerial view captures the quaint charm of the Beachside Village Resort, showcasing its coastal architecture. The vibrant green lawn is bordered by neatly trimmed shrubs, and outdoor seating areas are visible. The ocean sparkles in the background, with the road leading to the beach nearby.
Condo in Falmouth
4.86 out of 5 average rating, 7 reviews

1BR w/ Fireplace & Beach Access | Pool + Hot Tub

RandallRating, 5 stars2 months ago
We stayed off season, but still plenty to do and see. We loved it!
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 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!
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.
Condo in Falmouth
4.7 out of 5 average rating, 37 reviews

Lovely lakefront studio/condo with pool

LindaRating, 5 stars10 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.
Guest favorite
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, 5 reviews

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.
Condo in Falmouth
5 out of 5 average rating, 3 reviews

Two bedroom condo .on the water Falmouth, ma

RobertRating, 5 stars34 months ago
this is a great unit with lots of space for the family. so much to do on the cape and near by. but you can just park the car and just stay put with a beach and pool! everything went perfect
A community pool is surrounded by a tan deck and green lounge chairs. The pool features clear blue water and a ladder for entry. Lush greenery provides a natural backdrop, with a few buildings visible in the distance, emphasizing a peaceful environment.
Condo in New Seabury
4.92 out of 5 average rating, 12 reviews

5 Mi to Mashpee Commons: Coastal Mashpee Condo

JenniferRating, 5 stars10 months ago
Sweet, serene place, very peaceful area.
Superhost
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
4.72 out of 5 average rating, 18 reviews

Condo in Falmouth MA

MarkRating, 5 stars1 month ago
The Condo was clean & comfortable. Having two bedrooms with queen beds was perfect for us, and sharing the 1 bathroom worked fine. The price was better than most other options. It was peaceful, and very quiet during our stay (in early May). Having the pool available would be very nice in summer months.
Condo in Oak Bluffs
4.92 out of 5 average rating, 13 reviews

Spectacular Martha's Vineyard Island Home!

StephenRating, 5 stars26 months ago
Thank you for your hospitality. The stay was great and you were a pleasure to deal with.

Quick stats about vacation rentals with a pool in Oak Bluffs

  • Total rentals

    40 properties

  • Nightly prices starting at

    G$27,168 GYD 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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