Holiday rentals with a pool in Wainscott
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Wainscott
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 Wainscott rentals with a pool
House rentals with a pool
Home in Sag Harbor
4.81 out of 5 average rating, 108 reviewsSag Harbor Gem, private, 4 Bedrooms, Pool w Summer
6–13 Jun
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
25 Oct – 1 Nov
Home in East Hampton
4.96 out of 5 average rating, 25 reviewsBright Modern Home With Stunning Yard & Pool
9–16 Jan
Home in East Hampton
5.0 out of 5 average rating, 16 reviewsStunning 3 BR / 2.5 New Construction with Pool
24–31 Oct
Home in East Hampton
5.0 out of 5 average rating, 11 reviewsDesigner East Hampton with Bay Views + Pool
20–27 Nov
Home in Sag Harbor
5.0 out of 5 average rating, 9 reviewsSunny Sag Harbor Retreat
6–13 Nov
Home in East Hampton
5.0 out of 5 average rating, 46 reviewsFamily Friendly With Heated Pool
3–10 Oct
Home in East Hampton
4.93 out of 5 average rating, 14 reviewsCozy Beach Oasis in East Hampton + Pool
8–15 Sep
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 Greenport
4.93 out of 5 average rating, 124 reviewsBeautiful Waterview Condo on the North Fork of LI
31 Mar – 7 Apr
Condo in Montauk
4.99 out of 5 average rating, 181 reviewsMontauk Waterfront Condo w/ Sunset Views
24–31 Mar
Condo in Montauk
4.95 out of 5 average rating, 107 reviewsDeluxe Studio Apt@The Montauk Manor
12–19 Apr
Condo in Greenport
4.83 out of 5 average rating, 145 reviewsSound front condominium
29 Mar – 5 Apr
Condo in Montauk
4.8 out of 5 average rating, 231 reviewsMontauk Royal Atlantic Beach Resort North
20–27 Jul
Condo in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
25 Oct – 1 Nov
Condo in Greenport
4.89 out of 5 average rating, 80 reviewsSeaside Escape w Pool, Private Beach & Patio
28 Sep – 5 Oct
Home rentals with a private pool
Home in Remsenburg
4.95 out of 5 average rating, 64 reviewsExperience a Quiet Hamptons Getaway
24–31 Jan
Home in East Hampton
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
4–11 Apr
Home in East Hampton
4.79 out of 5 average rating, 39 reviewsEnchanting Home with Large Decks and Heated Pool
25 Jan – 1 Feb
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
14–21 Jan
Bungalow in East Hampton
4.93 out of 5 average rating, 99 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
2–9 May
Quick stats about holiday rentals with a pool in Wainscott
Total rentals
230 properties
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Pet-friendly rentals
110 properties allow pets
Family-friendly rentals
220 properties are a good fit for families
Total number of reviews
2.2K reviews
Nightly prices starting at
$202 NZD before taxes and fees
Destinations to explore
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