
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!

Home in Falmouth ~ 5 min drive to beach
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.

Mashpee Manor Pool House
House was very clean and comfortable. Kathleen was very responsive to all my inquiries both prior to and during our stay. House was easy drive to shopping and dinning as well as the local ponds and beaches. Although we did not cook if u plan to prepare meals be aware kitchen has limited pots and pans for cooking. Also would have like to have a tea pot to boil water. Otherwise had everything we needed for a wonderful stay

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

ShoestringBayHouse, waterfront & pool in Cotuit
Perfect stay - just be sure to bring or order sheets and towels!

Beautiful Edgartown Colonial with heated pool.
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!

Sippewissett Forest Magic by the Sea
We liked Thomas’s place very much. It is a nice renovated spacious and clean place. The pool is a very nice and cool addition. Thomas is a very generous landlord, we found a lot of linens and towels, lots of kitchen stuff and even some toys. Tom also left us a brand new inflatable shark to use. We enjoyed our stay very much. It is highly recommend.

Dog Friendly Cape Oasis | Pool+Beach |Tennis Court
What a great house and host. Cute neighborhood with water views just steps away. Close to everything - would definitely come back again!
Condo rentals with a pool

Relax....You're on Island Time......
Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.

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!

Private 3bdrm Condo Tashmoo Woods
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.

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.

Sunny 2bedroom condo w pool, walk to town
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!

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

Condo in Falmouth MA
Wonderfull place very peacefull and quiet . Beautiful lake in the Back as well. Patrick was very quick with his responses.overall great experience
Quick stats about vacation rentals with a pool in Oak Bluffs
Total rentals
40 properties
Nightly prices starting at
$130 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 National Seashore
- Sandwich Glass Museum
- Owen Park Beach
- Sagamore Beach
- New Silver Beach
- Onset Beach
- Lighthouse Beach
- Roger Williams Park Zoo
- Oakland Beach
- Grey's Beach
- Scusset Beach
- Pinehills Golf Club
- Nickerson State Park
- South Shore Beach
- Earle Road Beach
- Chapin Memorial Beach
- Agawam Hunt
- Oyster Harbors Beach
- Englewood Beach
- Springhill Beach
- Surfside Beach
- Pilgrim Beach
- Forest Beach
- Cahoon Hollow Beach
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