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
4.9 out of 5 average rating, 212 reviewsOcean Side, Amazing View, close to town/beach, Spa
Sep 7 – 14
Home in Colrain
4.88 out of 5 average rating, 112 reviewsThe 1770 House
Mar 7 – 14
Home in Oak Bluffs
4.93 out of 5 average rating, 169 reviewsSpectacular beach & pool combo; beautiful sunsets!
Mar 8 – 15
Home in Sagamore Beach
4.91 out of 5 average rating, 146 reviewsSpacious Upper Cape Retreat with Private Pool
Mar 10 – 17
Home in Deerfield
4.82 out of 5 average rating, 186 reviewsPerfectly Polished Deerfield Home 5 min to I-91
Sep 16 – 23
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Jul 8 – 15
Home in Lawrence
4.95 out of 5 average rating, 63 reviewsCozy single family ranch style main floor
Nov 12 – 19
Home in Plymouth
4.95 out of 5 average rating, 38 reviewsOur families slice of heaven
Oct 7 – 14
Condo rentals with a pool
Condo in Brewster
4.97 out of 5 average rating, 158 reviewsOcean Edge Resort-Pool Access-End Unit-2 bdr/2 bth
Nov 20 – 27
Condo in Provincetown
4.97 out of 5 average rating, 189 reviewsP-Town Beach Beauty on the Bay. Water View!
Dec 2 – 9
Condo in Brewster
4.92 out of 5 average rating, 103 reviews🌊Cape Escape Nestled in an Amenity Rich Resort🏖
Dec 29 – Jan 5
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
May 28 – Jun 4
Condo in Dennis
4.93 out of 5 average rating, 28 reviewsStylish & Modern Studio Condo - Steps to the Beach
Oct 25 – Nov 1
Condo in West Dennis, Dennis
4.79 out of 5 average rating, 29 reviewsHidden Hideaway
Apr 3 – 10
Condo in Acton
5.0 out of 5 average rating, 3 reviewsUpdated cozy one bedroom
Apr 17 – 24
Condo in Brewster
4.84 out of 5 average rating, 31 reviewsGolf Course Views and Pools
May 22 – 29
Destinations to explore
- Rentals with pools United States
- Rentals with pools Boston
- Rentals with an accessible height bed Massachusetts
- Apartment rentals Massachusetts
- Bed and breakfasts Massachusetts
- Rentals with a hot tub Massachusetts
- Barn rentals Massachusetts
- Villa rentals Massachusetts
- Beachfront rentals Massachusetts
- House rentals Massachusetts
- Family-friendly rentals Massachusetts
- Private suite rentals Massachusetts
- Kid-friendly rentals Massachusetts
- Rentals with an accessible height toilet Massachusetts
- Lakehouse rentals Massachusetts
- Boutique hotel rentals Massachusetts
- Waterfront rentals Massachusetts
- Monthly Rentals Massachusetts
- Rentals with lake access Massachusetts
- Rentals with an EV charger Massachusetts
- Loft rentals Massachusetts
- Rentals with breakfast Massachusetts
- Luxury rentals Massachusetts
- Townhouse rentals Massachusetts
- Rentals with beach access Massachusetts
- Condo rentals Massachusetts
- Cabin rentals Massachusetts
- Hotel rentals Massachusetts
- Rentals with a patio Massachusetts
- Farmstay rentals Massachusetts
- Rentals with a fireplace Massachusetts
- Mansion rentals Massachusetts
- Rentals with a washer and dryer Massachusetts
- Chalet rentals Massachusetts
- Cottage rentals Massachusetts
- Smoking-friendly rentals Massachusetts
- Fitness-friendly rentals Massachusetts
- Bungalow rentals Massachusetts
- Wheelchair accessible rentals Massachusetts
- Rentals with a home theater Massachusetts
- Beach house rentals Massachusetts
- Guesthouse rentals Massachusetts
- Rentals with a sauna Massachusetts
- Resort rentals Massachusetts
- Pet-friendly rentals Massachusetts
- Rentals with a kayak Massachusetts
- Rentals with outdoor seating Massachusetts
- Tiny house rentals Massachusetts
- Rentals with a fire pit Massachusetts
- Rentals with pools Cape Cod
- Rentals with pools New Hampshire
- 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