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 North Fork
4.97 out of 5 average rating, 200 reviewsPrivate Oasis W/Stunning Vinyard and Pool Views
Home in Sag Harbor
4.9 out of 5 average rating, 61 reviewsNewly Updated Home in Sag Harbor
Home in East Hampton
5 out of 5 average rating, 7 reviewsEast Hampton Getaway
Home in Hampton Bays
4.94 out of 5 average rating, 120 reviewsPeaceful Retreat in Immaculate Architect’s House
Home in East Hampton
5 out of 5 average rating, 24 reviewsStunning 3 BR / 2.5 New Construction with Pool
Home in Bridgehampton
4.92 out of 5 average rating, 90 reviewsPrivate Bridgehampton Cozy Fireplace
Home in East Hampton
4.94 out of 5 average rating, 35 reviewsSunny and Secluded Modernist Gem with Heated Pool
Home in East Hampton
4.96 out of 5 average rating, 47 reviewsContemporary East Hampton 4 Bedroom, Pool
Condo rentals with a pool
Condo in Montauk
4.91 out of 5 average rating, 23 reviews1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!
Condo in Montauk
5 out of 5 average rating, 20 reviewsSun N Sound Resort, Montauk, NY
Condo in North Fork
4.83 out of 5 average rating, 123 reviewsSeaside Escape w Pool, Private Beach + Patio
Condo in Montauk
5 out of 5 average rating, 209 reviewsMontauk Waterfront Condo w/ Sunset Views
Condo in North Fork
4.88 out of 5 average rating, 147 reviewsBeautiful Waterview Condo on the North Fork of LI
Condo in Bridgehampton
4.88 out of 5 average rating, 17 reviewsBridgehampton w/ Pool steps to town 3 bd 2.5 Bath
Condo in North Fork
5 out of 5 average rating, 107 reviews"Breathtaking Waterfront Water's Edge view"
Condo in Hampton Bays
4.95 out of 5 average rating, 42 reviewsA Unique Piece of Paradise, Water Front pool
Home rentals with a private pool
Home in East Hampton
4.94 out of 5 average rating, 16 reviewsWalk to Water. Stunning Home with Gorgeous Pool & Grounds.
Home in East Hampton
4.88 out of 5 average rating, 33 reviewsChic Poolside Hideaway in East Hampton
Home in Water Mill
4.92 out of 5 average rating, 120 reviewsBeach Barn w/ Sauna and Heated Pool - Dog Friendly
Home in Southampton
5 out of 5 average rating, 81 reviewsBest of Country and Beach Living
Home in East Hampton
4.82 out of 5 average rating, 45 reviewsEnchanting Home with Large Decks and Heated Pool
Home in Southampton
4.93 out of 5 average rating, 61 reviewsSouthampton Quiet Private Home/Pool 6min to Villag
Home in Southampton
4.95 out of 5 average rating, 20 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
Home in East Hampton
5 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
Quick stats about holiday rentals with a pool in Wainscott
Total rentals
250 properties
Nightly prices starting at
$325 NZD before taxes and fees
Total number of reviews
2.8K reviews
Family-friendly rentals
230 properties are a good fit for families
Pet-friendly rentals
120 properties allow pets
Rentals with dedicated workspaces
150 properties have a dedicated workspace
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