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Vacation rentals with a pool in The Hamptons

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Top-rated rentals with a pool in The Hamptons

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Guest favorite
Home in Southampton
Stunning 3 bed 2 bath home W Pool
Nestled on a serene an acre off a tranquil lane, this contemporary, designer-updated residence provides an idyllic Hamptons retreat. With 3 delightful bedrooms, 2 sleek bathrooms, and a seasonal heated pool amidst mature landscaping, you're promised a calming respite. We kindly ask that you familiarize yourself with the detailed disclosures, & guidelines. We maintain a strict policy against events, parties, and smoking. Please review the listing to ensure our home aligns with your preferences
$116 per night
Guest favorite
Condo in Montauk
Montauk 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)
$146 per night
Guest favorite
Cottage in Southampton
Secluded 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.
$335 per night

Popular amenities for The Hamptons rentals with a pool

House rentals with a pool

Guest favorite
Home in East Hampton
Fantastic East Hampton Village home with Pool
$114 per night
Guest favorite
Home in Shelter Island
Huge Island Getaway Pool HotTub Walk To Beach
$304 per night
Guest favorite
Home in Southampton
Waterview DogsStayFree! Kayaks Fireplace Ping-Pong
$262 per night
Guest favorite
Home in Sag Harbor
Exclusive Sag Harbor Compound
$450 per night
Guest favorite
Home in East Hampton
HeatedSaltWaterPool-Walk2Beach-Fireplace-Yard4Pup
$238 per night
Guest favorite
Home in Hampton Bays
Beach House Feel - newly renovated backyard Oasis
$400 per night
Superhost
Home in Sag Harbor
Sag Harbor Gem, private, 4 Bedrooms, Pool w Summer
$89 per night
Guest favorite
Home in East Hampton
Kid-friendly, heated pool, games room, near beach
$350 per night
Guest favorite
Home in East Hampton
Fully Furnished 4 BD in E Hampton w/ Heated Pool
$150 per night
Guest favorite
Home in Water Mill
Designer's Own, w Pool, 5 min. to Ocean & Village
$200 per night
Guest favorite
Home in East Hampton
Charming Cheerful Private Beach House
$327 per night
Guest favorite
Home in Sag Harbor
Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool
$139 per night

Condo rentals with a pool

Guest favorite
Condo in Montauk
Deluxe Studio Apt@The Montauk Manor
$129 per night
Guest favorite
Condo in Montauk
Montauk Royal Atlantic Beach Resort North
$125 per night
Guest favorite
Condo in Greenport
Beachside Waterview 2Br Condo w/ Pool in Greenport
$225 per night
Guest favorite
Condo in Greenport
Beautiful Waterview Condo on the North Fork of LI
$340 per night
Guest favorite
Condo in Greenport
Sound front condominium
$700 per night
Guest favorite
Condo in Montauk
Coastline View Studio
$999 per night
Guest favorite
Condo in Montauk
Renovated Beachfront Condo With An Incredible View
$379 per night
Superhost
Condo in Montauk
The Exclusive Resort in Montauk
$235 per night
Superhost
Condo in Montauk
Montauk Sunsets
$260 per night
Superhost
Condo in Hampton Bays
Waterfront Elevated Bungalow - Spectacular Views
$320 per night
Guest favorite
Condo in Montauk
Beautiful Condo on the Ocean Bluffs
$400 per night
Guest favorite
Condo in Greenport
"Breathtaking Waterfront Water's Edge view"
$448 per night

Home rentals with a private pool

Guest favorite
Home in Water Mill
Dog Friendly Hampton Beach Barn with Heated Pool
$622 per night
Guest favorite
Home in East Hampton
Explore the Water & Woods at a Relaxing Retreat
$607 per night
Superhost
Home in East Hampton
Quiet Oasis w/ Saltwater Pool 5min from Town/Beach
$510 per night
Guest favorite
Home in Southampton
Best of Country and Beach Living
$875 per night
Superhost
Home in East Hampton
Walk to Water. Stunning Home with Gorgeous Pool & Grounds.
$591 per night
Superhost
Home in Southampton
Southampton Private Home & Pool close to Village
$750 per night
Home in East Hampton
Saltbox with Separate Poolhouse in Northwest Woods
$650 per night
Home in East Hampton
Enchanting Home with Large Decks and Heated Pool
$500 per night
Home in Southampton
Perfect Getaway at Sunny Modern Shampton Lake House
$595 per night
Guest favorite
Bungalow in East Hampton
East Hampton Ranch with Access to Clearwater Private Beach
$750 per night
Home in East Hampton
Historical Estate Home with Backyard Pool
$1,000 per night
Guest favorite
Home in East Hampton
Chic Poolside Hideaway in East Hampton
$800 per night

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