
Vacation rentals with a pool in Oak Bluffs
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Top-rated 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

Beautiful Mashpee Home with Pool
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!

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

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

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

Sippewissett Forest Magic by the Sea
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…

New Construction Home with Pool in N. Falmouth
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!

Dog Friendly Cape Oasis | Pool+Beach |Tennis Court
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.

Jaws House - Great Harbors
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

1BR w/ Fireplace & Beach Access | Pool + Hot Tub
We stayed off season, but still plenty to do and see. We loved it!

Falmouth MA, Cape Cod Getaway
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!

Lovely lakefront studio/condo with pool
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.

Capecation! 3-bedroom condo with heated pool
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.

Two bedroom condo .on the water Falmouth, ma
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

5 Mi to Mashpee Commons: Coastal Mashpee Condo
Sweet, serene place, very peaceful area.

Condo in Falmouth MA
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.

Spectacular Martha's Vineyard Island Home!
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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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Easton Beach
- Sagamore Beach
- Sandwich Glass Museum
- Point Judith Country Club
- Coast Guard Beach
- Roger Williams Park Zoo
- Owen Park Beach
- Oakland Beach
- Onset Beach
- Nickerson State Park
- Inman Road Beach
- Pinehills Golf Club
- South Shore Beach
- Second Beach
- Fort Adams State Park
- Goddard Memorial State Park
- Pawtucket Country Club
- White Horse Beach