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
Mar 7 – 14
Home in Oak Bluffs
4.93 out of 5 average rating, 168 reviewsSpectacular beach & pool combo; beautiful sunsets!
Apr 8 – 15
Home in Hopkinton
4.95 out of 5 average rating, 138 reviewsHopkinton Mass 3+ Bedrooms - Great location!
Jul 17 – 24
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
Jun 23 – 30
Home in Lawrence
4.95 out of 5 average rating, 62 reviewsCozy single family ranch style main floor
Nov 11 – 18
Home in Dennis
4.89 out of 5 average rating, 27 reviewsWalk to the beach or sit poolside! Updated studio!
May 27 – Jun 3
Home in Plymouth
4.91 out of 5 average rating, 54 reviews5Br | Ocean View | Indoor Pool | Steps From Beach!
Jan 30 – Feb 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!
Oct 29 – Nov 5
Condo in Brewster
4.97 out of 5 average rating, 158 reviewsOcean Edge Resort-Pool Access-End Unit-2 bdr/2 bth
Nov 19 – 26
Condo in Provincetown
4.97 out of 5 average rating, 189 reviewsP-Town Beach Beauty on the Bay. Water View!
Jan 5 – 12
Condo in Brewster
4.92 out of 5 average rating, 103 reviews🌊Cape Escape Nestled in an Amenity Rich Resort🏖
Dec 21 – 28
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
Feb 1 – 8
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