Holiday 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.
Holiday rentals for every style
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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
9–16 Mar
Home in Oak Bluffs
4.93 out of 5 average rating, 169 reviewsSpectacular beach & pool combo; beautiful sunsets!
8–15 Mar
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
10–17 Mar
Home in Deerfield
4.82 out of 5 average rating, 186 reviewsPerfectly Polished Deerfield Home 5 min to I-91
16–23 Sep
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
13–20 Oct
Home in Lawrence
4.95 out of 5 average rating, 63 reviewsCozy single family ranch style main floor
23–30 Sep
Home in Nahant
4.97 out of 5 average rating, 67 reviewsHouse by the Sea - Glocca Morra
17–24 Dec
Apartment rentals with a pool
Apartment in Mashpee
4.97 out of 5 average rating, 101 reviewsSleep 6 @ New Seabury w/ Pool Access, All Seasons!
8–15 Feb
Apartment in Brewster
4.97 out of 5 average rating, 158 reviewsOcean Edge Resort-Pool Access-End Unit-2 bdr/2 bth
20–27 Nov
Apartment in Provincetown
4.97 out of 5 average rating, 189 reviewsP-Town Beach Beauty on the Bay. Water View!
28 Nov – 5 Dec
Apartment in Brewster
4.92 out of 5 average rating, 103 reviews🌊Cape Escape Nestled in an Amenity Rich Resort🏖
29 Dec – 5 Jan
Apartment in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
30 May – 6 Jun
Apartment in West Dennis, Dennis
4.79 out of 5 average rating, 29 reviewsHidden Hideaway
12–19 Nov
Apartment in Dennis
4.93 out of 5 average rating, 28 reviewsStylish & Modern Studio Condo - Steps to the Beach
25 Oct – 1 Nov
Apartment in Dennis
4.9 out of 5 average rating, 70 reviewsThe Sea Salt Studio - Steps to the Beach!
20–27 Apr
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