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 Oak Bluffs
4.94 out of 5 average rating, 170 reviewsSpectacular beach & pool combo; beautiful sunsets!
Dec 31 – Jan 7
Home in Colrain
4.88 out of 5 average rating, 112 reviewsThe 1770 House
Dec 29 – Jan 5
Home in Hopkinton
4.95 out of 5 average rating, 138 reviewsHopkinton Mass 3+ Bedrooms - Great location!
Jul 29 – Aug 5
Home in Sagamore Beach
4.91 out of 5 average rating, 146 reviewsSpacious Upper Cape Retreat with Private Pool
Apr 5 – 12
Home in Deerfield
4.81 out of 5 average rating, 187 reviewsPerfectly Polished Deerfield Home 5 min to I-91
Oct 27 – Nov 3
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
May 14 – 21
Home in Lawrence
4.95 out of 5 average rating, 63 reviewsCozy single family ranch style main floor
Nov 14 – 21
Home in Nahant
4.97 out of 5 average rating, 67 reviewsHouse by the Sea - Glocca Morra
Feb 15 – 22
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 26 – Nov 2
Condo in Provincetown
4.97 out of 5 average rating, 191 reviewsP-Town Beach Beauty on the Bay. Water View!
Mar 15 – 22
Condo in Brewster
4.92 out of 5 average rating, 103 reviews🌊Cape Escape Nestled in an Amenity Rich Resort🏖
Feb 23 – Mar 2
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Jun 8 – 15
Condo in West Dennis, Dennis
4.8 out of 5 average rating, 30 reviewsHidden Hideaway
Feb 19 – 26
Condo in Dennis
4.93 out of 5 average rating, 30 reviewsStylish & Modern Studio Condo - Steps to the Beach
Oct 25 – Nov 1
Condo in Brewster
4.84 out of 5 average rating, 31 reviewsGolf Course Views and Pools
May 9 – 16
Condo in Dennis
4.92 out of 5 average rating, 25 reviewsApril promo-Location-5 mins to beach-Pvt balcony
Mar 23 – 30
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