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
4.92 out of 5 average rating, 170 reviewsOur Secret Garden
Dec 28 – Jan 4
Home in Colrain
4.88 out of 5 average rating, 112 reviewsThe 1770 House
Mar 12 – 19
Home in Oak Bluffs
4.93 out of 5 average rating, 169 reviewsSpectacular beach & pool combo; beautiful sunsets!
Nov 24 – Dec 1
Home in Barnstable
4.93 out of 5 average rating, 104 reviewsMagical pool home with windmill/new kitchen
Nov 27 – Dec 4
Home in Hopkinton
4.95 out of 5 average rating, 138 reviewsHopkinton Mass 3+ Bedrooms - Great location!
Jul 22 – 29
Home in Deerfield
4.82 out of 5 average rating, 186 reviewsPerfectly Polished Deerfield Home 5 min to I-91
Oct 20 – 27
Home in Sagamore Beach
4.91 out of 5 average rating, 146 reviewsSpacious Upper Cape Retreat with Private Pool
Jan 30 – Feb 6
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Sep 25 – Oct 2
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
Oct 19 – 26
Condo in Provincetown
4.97 out of 5 average rating, 190 reviewsP-Town Beach Beauty on the Bay. Water View!
Mar 30 – Apr 6
Condo in Brewster
4.92 out of 5 average rating, 103 reviews🌊Cape Escape Nestled in an Amenity Rich Resort🏖
Feb 16 – 23
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Mar 19 – 26
Condo in West Dennis, Dennis
4.8 out of 5 average rating, 30 reviewsHidden Hideaway
May 3 – 10
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 Acton
5.0 out of 5 average rating, 3 reviewsUpdated cozy one bedroom
Dec 10 – 17
Condo in Brewster
4.84 out of 5 average rating, 31 reviewsGolf Course Views and Pools
May 22 – 29
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