
Holiday rentals with a pool in Massachusetts
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Massachusetts
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 Massachusetts rentals with a pool
House rentals with a pool

Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK

Stunning Cape Home - Inground Pool, 5 Min To Beach

The 1770 House

Happy Valley getaway

The Catamount Ski Haus with Pool & Hot Tub

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

Heated Pool. Hot Tub. Game Room. Beach Nearby!

Stunning luxury home with pool
Apartment rentals with a pool

P-Town Beach Beauty on the Bay. Water View!

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access

Jiminy Peak Apartment

Sunny 2bedroom condo w pool, walk to town

Bright Beach Condo • Walk to Sand & Shops

Mid Cape Cod, 3 Season Haven by Bass River

Spacious 2BR by the Sea in Falmouth
Other holiday rentals with a pool

Boston Modern Apt: Luxe Stay w/ Gym, Parking

Cozy Maynard Retreat: 3BR•Wood stove•kid friendly

Exquisite 1 Bedroom Suite-Charming,W/Private Entry

Sweet Dreams Retreat

Rustic Cabin in Campground

Cozy Private Suite halfway between Cape & Boston

NE Historical Mansion-pets and pet lovers welcome

Boston Designer Beach House | Near Airport
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- Rentals with pools United States
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