Vacation rentals with a pool in The Hamptons
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in The Hamptons
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Home in Shelter Island
4.97 out of 5 average rating, 189 reviewsHuge Island Getaway Pool HotTub Walk To Beach
Relaxation begins on the 6 minute ferry ride to this magical island. Summerfield is a spectacular, grand compound that has it all. Huge main house great for groups, 4700ft w/ privacy for all overlooking serene nature reserve. Star gaze in the bubbling hot tub, grill outside after a swim, play in the rec room with movie theater, pool table or ping pong,or watch TV by the fire! Open plan layout, gourmet kitchen, heated gunite pool, separate guest house. Prime location close to beach + restaurants.
Jan 27 – Feb 3
Condo in Montauk
4.99 out of 5 average rating, 177 reviewsMontauk Waterfront Condo w/ Sunset Views
Modern 1 Bedroom Condo in gated community (Rough Riders) with sunset views from beautiful deck. The community has multiple tennis courts, pool, jacuzzi, and sauna (pool area only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy fishing and swimming off the pier. The unit is less than a 5 minute car / Uber ride to town and a short 5-10 minute walk to Navy Beach and Duryea's. Strong wifi in unit, Smart TV ( Netflix, etc, - no cable)
Sep 21 – 28
Cottage in Southampton
4.96 out of 5 average rating, 162 reviewsSecluded Southampton Cottage w/Pool & Spa
*Follow Us on Insta @SimmerCottage* This designer-decorated cozy cottage near Southampton Village & a short drive or bike to the beach has a stocked chef's kitchen, cozy living room with wood-burning stone fireplace, 2 SmartTVs, whimsical dining room, 3 bedrooms, one bath & charming sunroom w/reading nooks. The Cottage has central heating/air & is set on a gated 1/2 acre w/hot-tub, outdoor dining for 8 on a stone patio, outdoor string lights, fire pit, gardener's potting station & gas BBQ.
Apr 12 – 19
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for The Hamptons rentals with a pool
House rentals with a pool
Home in East Hampton
4.92 out of 5 average rating, 125 reviewsKid-friendly, heated pool, games room, near beach
Sep 13 – 20
Home in Southampton
5.0 out of 5 average rating, 32 reviewsLuxury Hamptons Poolside Paradise w/ Outdoor Sauna
Mar 13 – 20
Home in East Hampton
4.96 out of 5 average rating, 55 reviewsEast Hampton Family Vacation Home
Feb 24 – Mar 3
Home in Southampton
5.0 out of 5 average rating, 37 reviewsBay View Stunner, Modern 6 Bedroom w Heated Pool
May 16 – 23
Home in Sag Harbor
4.84 out of 5 average rating, 45 reviewsModern Home in Sag Harbor, NY
May 16 – 23
Home in Sag Harbor
4.98 out of 5 average rating, 85 reviewsDesigner in Sag Harbor 5 Br 1 block from water
Mar 20 – 27
Home in East Hampton
5.0 out of 5 average rating, 57 reviewsSerene East Hampton Escape - Pool Open 4/19
May 6 – 13
Home in East Hampton
4.93 out of 5 average rating, 14 reviewsCozy Beach Oasis in East Hampton + Pool
Sep 15 – 22
Home in Hampton Bays
4.97 out of 5 average rating, 29 reviews3 bedroom house with heated, salt water pool
Dec 31 – Jan 7
Home in East Hampton
4.9 out of 5 average rating, 29 reviewsNewly Renovated Hamptons Home with Heated Pool
May 12 – 19
Home in East Hampton
5.0 out of 5 average rating, 22 reviewsBook your summer Getaway(Heated Pool+Peloton Bike)
Jan 17 – 24
Home in East Hampton
4.96 out of 5 average rating, 24 reviewsBright Modern Home With Stunning Yard & Pool
Jan 31 – Feb 7
Condo rentals with a pool
Condo in Greenport
4.91 out of 5 average rating, 107 reviewsBeachside Waterview 2Br Condo w/ Pool in Greenport
May 12 – 19
Condo in Montauk
4.95 out of 5 average rating, 106 reviewsDeluxe Studio Apt@The Montauk Manor
Aug 23 – 30
Condo in Montauk
4.8 out of 5 average rating, 228 reviewsMontauk Royal Atlantic Beach Resort North
Aug 8 – 15
Condo in Greenport
4.83 out of 5 average rating, 141 reviewsSound front condominium
Mar 14 – 21
Condo in Greenport
4.93 out of 5 average rating, 122 reviewsBeautiful Waterview Condo on the North Fork of LI
Jul 19 – 26
Condo in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
Sep 25 – Oct 2
Condo in Bridgehampton
4.92 out of 5 average rating, 13 reviewsBridgehampton w/ Pool steps to town 3 bd 2.5 Bath
Nov 15 – 22
Condo in Montauk
4.74 out of 5 average rating, 38 reviewsThe Exclusive Resort in Montauk
Jun 5 – 12
Condo in Montauk
4.88 out of 5 average rating, 17 reviews1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!
Jun 24 – Jul 1
Condo in Montauk
4.82 out of 5 average rating, 87 reviewsBeautiful Condo on the Ocean Bluffs
Sep 19 – 26
Condo in Greenport
5.0 out of 5 average rating, 90 reviews"Breathtaking Waterfront Water's Edge view"
Feb 3 – 10
Condo in Montauk
4.81 out of 5 average rating, 26 reviewsMontauk Sunsets
Jun 3 – 10
Home rentals with a private pool
Home in Remsenburg
4.95 out of 5 average rating, 64 reviewsExperience a Quiet Hamptons Getaway
Sep 29 – Oct 6
Home in East Hampton
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
Mar 4 – 11
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
May 17 – 24
Home in East Hampton
4.79 out of 5 average rating, 39 reviewsEnchanting Home with Large Decks and Heated Pool
Apr 11 – 18
Bungalow in East Hampton
4.93 out of 5 average rating, 99 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
Apr 14 – 21
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