
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.
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!!

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.

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 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

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!

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

Martha’s Vineyard Condo * Near Ferry
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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- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Cape Cod National Seashore
- Craigville Beach
- Duxbury Beach
- Easton Beach
- Sandwich Glass Museum
- Owen Park Beach
- Sagamore Beach
- New Silver Beach
- Onset Beach
- Lighthouse Beach
- Roger Williams Park Zoo
- Oakland Beach
- Coast Guard Beach
- Pinehills Golf Club
- Nickerson State Park
- South Shore Beach
- Chapin Memorial Beach
- Grey's Beach
- Scusset Beach
- Corn Hill Beach