Vacation rentals with a pool in Southampton
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Southampton
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 Southampton rentals with a pool
House rentals with a pool
Home in Hampton Bays
4.94 out of 5 average rating, 111 reviewsBeautiful Hampton’s Home Pool/Tennis/HotTub/Sauna
Mar. 8 – 15
Home in Sag Harbor
4.82 out of 5 average rating, 132 reviewsNew! Sag Harbor Village Pool, Hot Tub &Beach House
Oct. 31 – Nov. 7
Home in Shelter Island
4.97 out of 5 average rating, 194 reviewsHuge Island Getaway Pool HotTub Walk To Beach
Feb. 6 – 13
Home in Sag Harbor
4.81 out of 5 average rating, 109 reviewsSag Harbor Gem, private, 4 Bedrooms, Pool w Summer
Jun. 6 – 13
Home in East Hampton
4.92 out of 5 average rating, 128 reviewsHeated pool, games room, near beach, kid-friendly
Oct. 23 – 30
Home in Southampton
5.0 out of 5 average rating, 20 reviewsModern Southampton home, heated pool, pickleball
Mar. 21 – 28
Home in Southampton
4.97 out of 5 average rating, 35 reviewsBeautiful Southampton Village Home with Pool
Oct. 21 – 28
Home in Southampton
4.9 out of 5 average rating, 67 reviewsClassic Southampton Village Home w/ Pool
May 29 – Jun. 5
Condo rentals with a pool
Condo in Greenport
4.91 out of 5 average rating, 107 reviewsBeachside Waterview 2Br Condo w/ Pool in Greenport
Oct. 25 – Nov. 1
Condo in Montauk
4.99 out of 5 average rating, 181 reviewsMontauk Waterfront Condo w/ Sunset Views
Mar. 18 – 25
Condo in Greenport
4.92 out of 5 average rating, 125 reviewsBeautiful Waterview Condo on the North Fork of LI
Nov. 10 – 17
Condo in Greenport
4.83 out of 5 average rating, 145 reviewsSound front condominium
Oct. 9 – 16
Condo in Montauk
4.95 out of 5 average rating, 107 reviewsDeluxe Studio Apt@The Montauk Manor
Aug. 26 – Sep. 2
Condo in Montauk
4.8 out of 5 average rating, 232 reviewsMontauk Royal Atlantic Beach Resort North
Jul. 20 – 27
Condo in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
Oct. 26 – Nov. 2
Condo in Greenport
4.89 out of 5 average rating, 80 reviewsSeaside Escape w Pool, Private Beach & Patio
Oct. 22 – 29
Home rentals with a private pool
Home in East Hampton
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
Apr. 5 – 12
Home in Remsenburg
4.95 out of 5 average rating, 64 reviewsExperience a Quiet Hamptons Getaway
Mar. 26 – Apr. 2
Bungalow in East Hampton
4.93 out of 5 average rating, 99 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
May 14 – 21
Home in East Hampton
4.79 out of 5 average rating, 39 reviewsEnchanting Home with Large Decks and Heated Pool
Oct. 25 – Nov. 1
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
Jan. 14 – 21
Quick stats about vacation rentals with a pool in Southampton
Total rentals
340 properties
Rentals with dedicated workspaces
200 properties have a dedicated workspace
Pet-friendly rentals
150 properties allow pets
Family-friendly rentals
300 properties are a good fit for families
Total number of reviews
4.7K reviews
Nightly prices starting at
$14 CAD before taxes and fees
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