Vacation 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.
Vacation 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
Home in Plymouth
Our Secret Garden
Home in Colrain
The 1770 House
Home in North Truro
Heated Pool all year, Beach, Pets, ADA, EV Charge
Home in Oak Bluffs
Spectacular beach & pool combo; beautiful sunsets!
Home in Hopkinton
Hopkinton Mass 3+ Bedrooms - Great location!
Home in Sagamore Beach
Spacious Upper Cape Retreat with Private Pool
Home in Deerfield
Perfectly Polished Deerfield Home 5 min to I-91
Home in Sheffield
Race Mountain House
Condo rentals with a pool
Condo in Mashpee
Sleep 6 @ New Seabury w/ Pool Access, All Seasons!
Condo in Provincetown
P-Town Beach Beauty on the Bay. Water View!
Condo in Brewster
Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth
Condo in Hancock
Cozy Condo @ Jiminy Peak
Condo in Brewster
🌊Cape Escape Nestled in an Amenity Rich Resort🏖
Condo in West Dennis, Dennis
Hidden Hideaway
Condo in Dennis
June promo-Pool-5 mins to beach-Private balcony
Condo in Dennis
The Sea Salt Studio - Steps to the Beach!
Destinations to explore
- Rentals with pools United States
- Rentals with pools Boston
- Cottage rentals Massachusetts
- Bungalow rentals Massachusetts
- Fitness-friendly rentals Massachusetts
- Beachfront rentals Massachusetts
- Ski-in/ski-out rentals Massachusetts
- Pet-friendly rentals Massachusetts
- Barn rentals Massachusetts
- Rentals with a fireplace Massachusetts
- Mansion rentals Massachusetts
- Rentals with a home theater Massachusetts
- Monthly Rentals Massachusetts
- Guesthouse rentals Massachusetts
- Rentals with a patio Massachusetts
- Farmstay rentals Massachusetts
- Lake house rentals Massachusetts
- Beach house rentals Massachusetts
- Rentals with an accessible height bed Massachusetts
- Loft rentals Massachusetts
- Family-friendly rentals Massachusetts
- Rentals with an accessible height toilet Massachusetts
- Apartment rentals Massachusetts
- Luxury rentals Massachusetts
- Rentals with a kayak Massachusetts
- Smoking-friendly rentals Massachusetts
- Rentals with breakfast Massachusetts
- Hotel rentals Massachusetts
- Rentals with a sauna Massachusetts
- Serviced apartment rentals Massachusetts
- Rentals with a washer and dryer Massachusetts
- Rentals with lake access Massachusetts
- Rentals with a firepit Massachusetts
- Waterfront rentals Massachusetts
- Rentals with a hot tub Massachusetts
- Rentals with beach access Massachusetts
- Chalet rentals Massachusetts
- Rentals with an EV charger Massachusetts
- Resort rentals Massachusetts
- Kid-friendly rentals Massachusetts
- Tiny house rentals Massachusetts
- Wheelchair accessible rentals Massachusetts
- House rentals Massachusetts
- Villa rentals Massachusetts
- Boutique hotel rentals Massachusetts
- Private suite rentals Massachusetts
- Bed and breakfasts Massachusetts
- Condo rentals Massachusetts
- Townhouse rentals Massachusetts
- Cabin rentals Massachusetts
- Rentals with outdoor seating Massachusetts
- Rentals with pools Cape Cod
- Rentals with pools New Hampshire
- Yurt Rentals United States
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- Large Villas United Kingdom
- House Rentals with a Pool United States
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- Apartments with a Hot Tub United States
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- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom