
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
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 Barnstable
4.75 out of 5 average rating, 16 reviewsStunning Cape Home - Inground Pool, 5 Min To Beach

Home in Marblehead
5 out of 5 average rating, 10 reviewsLarge Pool, Nature Trails, Redd's Pond, 4-Bed

Home in Mashpee
5 out of 5 average rating, 13 reviewsCape Cod multi-structure family compound with Pool

Home in Worcester
4.96 out of 5 average rating, 97 reviewsCourtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

Home in Harwich
4.79 out of 5 average rating, 14 reviews4 BD slice of Harwich Heaven

Home in East Sandwich
4.92 out of 5 average rating, 64 reviewsLarge Home Heated Swimming Pool Private Beach

Home in Great Barrington
4.98 out of 5 average rating, 41 reviewsSix-bedroom country house with pool and hot tub

Home in Yarmouth
4.94 out of 5 average rating, 16 reviewsRoom for multiple families!
Condo rentals with a pool

Condo in Provincetown
4.97 out of 5 average rating, 209 reviewsP-Town Beach Beauty on the Bay. Water View!

Condo in Brewster
4.97 out of 5 average rating, 178 reviewsOcean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

Condo in Dennis
4.89 out of 5 average rating, 28 reviews1BR 2nd Floor Condo with pool

Condo in Provincetown
4.9 out of 5 average rating, 10 reviewsLuxury Waterfront Getaway

Condo in Tisbury
4.91 out of 5 average rating, 47 reviewsPrivate 3bdrm Condo Tashmoo Woods

Condo in West Dennis, Dennis
4.84 out of 5 average rating, 51 reviewsHidden Hideaway

Condo in Provincetown
4.93 out of 5 average rating, 100 reviewsModern, clean waterviews

Condo in Brewster
5 out of 5 average rating, 71 reviewsOcean Edge Resort/Pool access/2bedroom-2bath Condo
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