Vacation rentals with a pool in Oak Bluffs
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Oak Bluffs
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Oak Bluffs rentals with a pool
House rentals with a pool
Home in Mashpee
5.0 out of 5 average rating, 13 reviewsCape Cod multi-structure family compound with Pool
Mar. 7 – 14
Home in Rochester
4.95 out of 5 average rating, 60 reviewsSouth Coast Serenity - Quintessential New England
Apr. 8 – 15
Home in Falmouth
4.94 out of 5 average rating, 17 reviewsDog Friendly Cape Oasis | Pool+Beach |Tennis Court
Apr. 18 – 25
Home in New Bedford
4.78 out of 5 average rating, 153 reviewsPoseidon's Palace - 2.0
Nov. 14 – 21
Home in Mashpee
4.88 out of 5 average rating, 16 reviewsBeautiful Mashpee Home with Pool
Aug. 18 – 25
Home in Falmouth
5.0 out of 5 average rating, 10 reviewsHome in Falmouth ~ 5 min drive to beach
Jul. 8 – 15
Home in Barnstable
4.9 out of 5 average rating, 10 reviewsbeautiful cape cod home with pool and hot spa
Dec. 24 – 31
Home in Falmouth
4.93 out of 5 average rating, 15 reviewsGorgeous Cape Cod Property!
Jan. 12 – 19
Condo rentals with a pool
Condo in Tisbury
4.75 out of 5 average rating, 4 reviewsMartha’s Vineyard Ground Condo * Pool * Near Ferry
Sep. 16 – 23
Condo in Oak Bluffs
4.66 out of 5 average rating, 38 reviewsPerfect 2BR Island Inn | Patio | Pool
Mar. 12 – 19
Condo in Tisbury
4.74 out of 5 average rating, 19 reviewsHeart of VH, w/ac, pool & harborview
Feb. 11 – 18
Condo in Oak Bluffs
4.92 out of 5 average rating, 13 reviewsSpectacular Martha's Vineyard Island Home!
Feb. 20 – 27
Condo in Mashpee
5.0 out of 5 average rating, 9 reviewsCoastal Mashpee Condo: 2 Mi to Beach + Pool Access
May 21 – 28
Condo in Falmouth
4.78 out of 5 average rating, 32 reviewsLovely lakefront condo with pool
Sep. 1 – 8
Condo in Falmouth
4.82 out of 5 average rating, 11 reviewsFalmouth MA, Cape Cod Getaway
Jun. 8 – 15
Condo in Falmouth
5.0 out of 5 average rating, 3 reviewsTwo bedroom condo .on the water Falmouth, ma
Oct. 12 – 19
Quick stats about vacation rentals with a pool in Oak Bluffs
Total rentals
80 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
1.6K reviews
Nightly prices starting at
$178 CAD before taxes and fees
Destinations to explore
- Cape Cod Vacation rentals
- Martha's Vineyard Vacation rentals
- Cambridge Vacation rentals
- Montauk Vacation rentals
- Nantucket Vacation rentals
- Salem Vacation rentals
- Newport Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Rentals with pools United States
- Rentals with pools Boston
- Rentals with pools Cape Cod
- Rentals with pools Martha's Vineyard
- Rentals with pools Massachusetts
- Cottage rentals Oak Bluffs
- Apartment rentals Oak Bluffs
- Boutique hotel rentals Oak Bluffs
- Rentals with a patio Oak Bluffs
- Monthly Rentals Oak Bluffs
- House rentals Oak Bluffs
- Rentals with lake access Oak Bluffs
- Rentals with a kayak Oak Bluffs
- Rentals with a hot tub Oak Bluffs
- Rentals with a washer and dryer Oak Bluffs
- Beachfront rentals Oak Bluffs
- Rentals with outdoor seating Oak Bluffs
- Condo rentals Oak Bluffs
- Rentals with beach access Oak Bluffs
- Family-friendly rentals Oak Bluffs
- Waterfront rentals Oak Bluffs
- Rentals with a firepit Oak Bluffs
- Rentals with breakfast Oak Bluffs
- Pet-friendly rentals Oak Bluffs
- Kid-friendly rentals Oak Bluffs
- Bed and breakfasts Oak Bluffs
- Rentals with a fireplace Oak Bluffs
- Rentals with pools Dukes County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom