Holiday 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.
Holiday 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
8–15 Mar
Home in Sag Harbor
4.82 out of 5 average rating, 132 reviewsNew! Sag Harbor Village Pool, Hot Tub &Beach House
12–19 Nov
Home in Southampton
5.0 out of 5 average rating, 20 reviewsModern Southampton home, heated pool, pickleball
6–13 Nov
Home in Sag Harbor
4.98 out of 5 average rating, 88 reviewsPerfection in Sag Harbor 5 Br 1 block from water
4–11 Nov
Home in Southampton
4.9 out of 5 average rating, 67 reviewsClassic Southampton Village Home w/ Pool
29 May – 5 Jun
Home in Southampton
5.0 out of 5 average rating, 45 reviewsPerfect Family Escape with Heated Pool
6–13 Sep
Home in Hampton Bays
4.97 out of 5 average rating, 29 reviews3 bedroom house with heated, salt water pool
18–25 Apr
Home in Southampton
4.96 out of 5 average rating, 47 reviewsSouthampton Village Newly Built Gem
21–28 Nov
Condo rentals with a pool
Condo in Greenport
4.91 out of 5 average rating, 107 reviewsBeachside Waterview 2Br Condo w/ Pool in Greenport
8–15 Oct
Condo in Montauk
4.99 out of 5 average rating, 181 reviewsMontauk Waterfront Condo w/ Sunset Views
17–24 Mar
Condo in Montauk
4.95 out of 5 average rating, 107 reviewsDeluxe Studio Apt@The Montauk Manor
30 Mar – 6 Apr
Condo in Greenport
4.93 out of 5 average rating, 124 reviewsBeautiful Waterview Condo on the North Fork of LI
10–17 Nov
Condo in Greenport
4.83 out of 5 average rating, 145 reviewsSound front condominium
30 May – 6 Jun
Condo in Montauk
4.8 out of 5 average rating, 232 reviewsMontauk Royal Atlantic Beach Resort North
20–27 Jul
Condo in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
26 Oct – 2 Nov
Condo in Greenport
4.89 out of 5 average rating, 80 reviewsSeaside Escape w Pool, Private Beach & Patio
8–15 Apr
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
4–11 Apr
Home in Remsenburg
4.95 out of 5 average rating, 64 reviewsExperience a Quiet Hamptons Getaway
24–31 Jan
Bungalow in East Hampton
4.93 out of 5 average rating, 99 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
15–22 May
Home in East Hampton
4.79 out of 5 average rating, 39 reviewsEnchanting Home with Large Decks and Heated Pool
2–9 Apr
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
14–21 Jan
Quick stats about holiday 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
$17 NZD before taxes and fees
Destinations to explore
- New City Holiday rentals
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