
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

Stunning Cape Home - Inground Pool, 5 Min To Beach

The 1770 House

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

The Catamount Ski Haus with Pool & Hot Tub

XL Cape Retreat - Pool - Hot Tub - 5min to Beach!

Mansion with Heated Pool Near Ocean

Serene South Deerfield Retreat

Mountain Blossom Retreat by Evergreen Home
Condo 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

Hidden Hideaway

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

XL Estate: 2 Homes-Pool-Tennis-Game Barn - 20 ppl

Boston Modern Apt: Luxe Stay w/ Gym, Parking

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

Sweet Dreams Retreat

Rustic Cabin in Campground

Cozy Private Suite halfway between Cape & Boston

NE Historical Mansion-pets and pet lovers welcome

Modern Studio Apt with Pool
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- Rentals with pools United States
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