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 Colrain
4.88 out of 5 average rating, 112 reviewsThe 1770 House
Nov 26 – Dec 3
Home in Barnstable
4.93 out of 5 average rating, 104 reviewsMagical pool home with windmill/new kitchen
Nov 4 – 11
Home in Hopkinton
4.95 out of 5 average rating, 138 reviewsHopkinton Mass 3+ Bedrooms - Great location!
Home in Sagamore Beach
4.91 out of 5 average rating, 146 reviewsSpacious Upper Cape Retreat with Private Pool
Mar 16 – 23
Home in Deerfield
4.82 out of 5 average rating, 186 reviewsPerfectly Polished Deerfield Home 5 min to I-91
Sep 18 – 25
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Sep 28 – Oct 5
Home in Lawrence
4.95 out of 5 average rating, 63 reviewsCozy single family ranch style main floor
Nov 16 – 23
Home in Nahant
4.97 out of 5 average rating, 67 reviewsHouse by the Sea - Glocca Morra
Nov 29 – Dec 6
Condo rentals with a pool
Condo in Mashpee
4.97 out of 5 average rating, 101 reviewsSleep 6 @ New Seabury w/ Pool Access, All Seasons!
Nov 7 – 14
Condo in Brewster
4.97 out of 5 average rating, 158 reviewsOcean Edge Resort-Pool Access-End Unit-2 bdr/2 bth
Jan 2 – 9
Condo in Provincetown
4.97 out of 5 average rating, 190 reviewsP-Town Beach Beauty on the Bay. Water View!
Oct 17 – 24
Condo in Brewster
4.92 out of 5 average rating, 103 reviews🌊Cape Escape Nestled in an Amenity Rich Resort🏖
Jan 6 – 13
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Jun 5 – 12
Condo in West Dennis, Dennis
4.8 out of 5 average rating, 30 reviewsHidden Hideaway
Apr 22 – 29
Condo in Dennis
4.93 out of 5 average rating, 29 reviewsStylish & Modern Studio Condo - Steps to the Beach
Oct 25 – Nov 1
Condo in Dennis
4.9 out of 5 average rating, 70 reviewsThe Sea Salt Studio - Steps to the Beach!
Feb 9 – 16
Destinations to explore
- Rentals with pools United States
- Rentals with pools Boston
- Villa rentals Massachusetts
- Farmstay rentals Massachusetts
- Townhouse rentals Massachusetts
- Cabin rentals Massachusetts
- Rentals with lake access Massachusetts
- Chalet rentals Massachusetts
- Rentals with a washer and dryer Massachusetts
- Loft rentals Massachusetts
- Rentals with a fireplace Massachusetts
- Rentals with an EV charger Massachusetts
- Wheelchair accessible rentals Massachusetts
- Waterfront rentals Massachusetts
- Rentals with a home theater Massachusetts
- Family-friendly rentals Massachusetts
- Rentals with beach access Massachusetts
- Rentals with an accessible height toilet Massachusetts
- Ski-in/ski-out rentals Massachusetts
- Monthly Rentals Massachusetts
- Apartment rentals Massachusetts
- Kid-friendly rentals Massachusetts
- Mansion rentals Massachusetts
- Private suite rentals Massachusetts
- Smoking-friendly rentals Massachusetts
- Fitness-friendly rentals Massachusetts
- Bungalow rentals Massachusetts
- Beachfront rentals Massachusetts
- House rentals Massachusetts
- Beach house rentals Massachusetts
- Guesthouse rentals Massachusetts
- Boutique hotel rentals Massachusetts
- Hotel rentals Massachusetts
- Pet-friendly rentals Massachusetts
- Barn rentals Massachusetts
- Bed and breakfasts Massachusetts
- Rentals with an accessible height bed Massachusetts
- Rentals with a kayak Massachusetts
- Rentals with outdoor seating Massachusetts
- Rentals with a patio Massachusetts
- Rentals with a sauna Massachusetts
- Cottage rentals Massachusetts
- Condo rentals Massachusetts
- Rentals with a fire pit Massachusetts
- Rentals with breakfast Massachusetts
- Luxury rentals Massachusetts
- Resort rentals Massachusetts
- Lakehouse rentals Massachusetts
- Rentals with a hot tub Massachusetts
- Tiny house rentals 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