
Holiday 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.
Holiday 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

Beautiful Mashpee Home with Pool

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

Contemporary Gem with Private Pool!

Home in Falmouth ~ 5 min drive to beach

Mashpee Manor Pool House

Sunny Cape w/Private Pool, Steps to Private Lake

Sippewissett Forest Magic by the Sea

Dog Friendly Cape Oasis | Pool+Beach |Tennis Court
Apartment rentals with a pool

Surfside Resort Cape Cod, Falmouth MA

Falmouth MA, Cape Cod Getaway

Lovely lakefront studio/condo with pool

InnSeason Resorts Surfside

Island Inn - Two Bedroom Suite - 1A - Oak Bluffs,

Two bedroom condo .on the water Falmouth, ma

5 Mi to Mashpee Commons: Coastal Mashpee Condo

Condo in Falmouth MA
Other holiday rentals with a pool

Greenwood family fun.

New Seabury pool/hot tub near beach,Popponesett

Beautiful Cape Cod Retreat w/Pool

Summer 2025 Open!Walk to Great Pond, central a/c

New Pool, beach, kayak, Marina in Barnstable.

Beautiful Family Friendly House with Pool

Private POOL*New Seabury* 3 bedroom

2BR Golf Course View | Private Pool | Patio | W/D
Quick stats about holiday rentals with a pool in Oak Bluffs
Total rentals
40 properties
Nightly prices starting at
£110 before taxes and fees
Total number of reviews
790 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
Destinations to explore
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- Rentals with outdoor seating Oak Bluffs
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- Rentals with pools Dukes County
- Rentals with pools Massachusetts
- Rentals with pools United States
- Cape Cod
- Mayflower Beach
- Cape Cod National Seashore
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Onset Beach
- Point Judith Country Club
- Easton Beach
- Oakland Beach
- Coast Guard Beach
- Horseneck Beach State Reservation
- White Horse Beach
- Second Beach
- Roger Williams Park Zoo
- Chapin Memorial Beach
- Pinehills Golf Club
- Nauset Beach
- Island Park Beach
- Lighthouse Beach
- The Breakers
- South Shore Beach
- Goddard Memorial State Park