
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.

Modern East Hampton Home w/ Heated Saltwater Pool
Peace and serenity in East Hampton and minutes from the Village. This exquisite modern home features high-end finishes such as Sub-Zero and Wolf appliances, quartzite waterfall kitchen island and counters, marble tiled bathrooms, designer mid-century decor and separately zoned air conditioning. The heated saltwater pool is surrounded by a bluestone patio, Ipe lighted deck and huge yard. The house features two wood-burning fireplaces in the living room and den and an outdoor fire-pit. RR# 26-891
4.89 out of 5 average rating, 119 reviews
Stylish+Modern Cape w/Saltwater Pool-5min to Beach
Stylish+Modern Cape Beach House nestled in Hampton Bays South of the highway, 5 min drive to beaches. Heated Saltwater Pool. 4 Bedrooms+Crib room & Office. 2 Bathrooms. Outdoor deck w/family dining+BBQ. Fully-fenced, tree-lined back yard w/ beautiful sunsets. Upstairs King bedroom w/ensuite bthrm + Twin bedroom directly off master. Main floor has another King bedroom+Twin bedroom, master bath, lounge+kitchen w/huge sit-around island. TV Den. Central AC. 15 min walk/ 2 min drive to shops+train.
4.97 out of 5 average rating, 159 reviews
Southampton Village Newly Built Gem
Enjoy a stylish experience at this 3765+ sq ft., just built, SH Village gem! Beautiful and bright spacious home with 5 well appointed bedrooms, multiple custom closets and 5.5 baths (4 ensuite). Luxurious lighting fixtures throughout the home. Living room fireplace, vaulted wooden beam kitchen ceiling with formal dining for 10 plus. Gunite pool and spa, with multiple outdoor seating areas. Expansive media room with 75 inch TV and room length comfy cloud sofa. Two sets of washers and dryers.
4.97 out of 5 average rating, 103 reviews
Modern farmhouse w/ pool, beach, horses and winery
A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.
4.93 out of 5 average rating, 138 reviews
Designer's Own, w Pool, 5 min. to Ocean & Village
Our 4BR airy home in a prime Hamptons location--Water Mill South--offers comfort, luxury, and tranquility, all while being just 5 min. away from ocean beaches, restaurants in Bridgehampton Village, and the area's best fields and farm stands. Impeccably renovated, comfortable, family-oriented traditional shingle house is in a quiet, established neighborhood perfect for walks or bike rides. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking
4.88 out of 5 average rating, 105 reviews
Family Retreat with Heated Pool, Hot Tub, Sauna.
🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants
4.96 out of 5 average rating, 189 reviews
Pool|Golf Sim|HotTub|Movie|Games|Firepit|Golf Open
Insta: @staywithhamptonsmama PINKWOOD PLAYHOUSE is the perfect spot for your Hamptons stay, offering elevated design and relaxed luxury with laid back beach vibes. Perfect for families, friends or couples. This stylish and serene home features 4 bedrooms, 2.5 bathrooms, a fully equipped kitchen, soaring ceilings, games room and movie room. Bring the outdoors in with oversized windows and over 1000 square feet of deck space overlooking the gorgeous pool (can be heated for a fee).
4.95 out of 5 average rating, 101 reviews
Sag Harbor, Designer w large Pool (3 bed/2.5 bath)
Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds, 2.5 baths - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond -Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action. NOTE: Due to water leakage issues, the bath in pool house is not available
4.86 out of 5 average rating, 139 reviews
5 min to EH town w/pool, playground, self check-in
INSTANT BOOK/ dates are current. Private and Pristine 3 bed / 2 bath home in the heart of East Hampton set on 1.3 acres. Home features a chef's kitchen, in-ground gated pool, and pure privacy and relaxation. Close proximity to East Hampton Village (5 mins) and East Hampton, Amangansett and Bay Beaches (7mins), Montauk (20 mins), Sag Harbor (15 mins). Kids adore the huge playground! Entire property fenced-in to ensure the safety of kids! Heated Pool open: Memorial Day - Sept 30.
4.93 out of 5 average rating, 142 reviews
Stunning Hamptons Waterfront Escape w/ Sunset View
Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views and sunset from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Our pool will close on September 15th, 2026 and will reopen May 29, 2027.
4.87 out of 5 average rating, 144 reviews
Coastal Retreat|Heated Saltwater Pool|5 MinToBeach
Unwind in Hamptons Bliss! A coastal oasis awaits at this exquisite vacation house. Immerse yourself in luxury, from the elegant interiors to the serene outdoor retreat including a massive fenced-in salt water heated pool (Memorial Day to Labor Day) that will leave you in awe. Indulge in beachside bliss, upscale shopping, and culinary delights. Create memories that will linger long after the sun sets over the horizon. Your dream Hamptons getaway starts here!
4.94 out of 5 average rating, 119 reviews
Luxury Hamptons Home with Heated Saltwater Pool
Get away from it all in this meticulously renovated Westhampton Beach home. Pull up to the cottage in the heart of Westhampton Beach, a place that delivers all the Hamptons have to offer, all while being within a two hour drive of NYC. No detail was overlooked in the renovation of this cottage… the beauty is only matched by the comfort and function. With the open floor plan, sunny kitchen, furnished open air patio, you won’t want to leave.
4.98 out of 5 average rating, 179 reviewsPopular amenities for The Hamptons rentals with a pool
House rentals with a pool

Astounding Watermill 5 Bedroom home with Pool
4.94 out of 5 average rating, 167 reviews
East Hampton Oasis - Pool and Hot Tub
4.83 out of 5 average rating, 144 reviews
East Hampton Home: Heated Pool, Gym, Fully Fenced
4.97 out of 5 average rating, 112 reviews
Pool Central Private Bridgehampton Home
4.93 out of 5 average rating, 109 reviews
Dream Home with a wonderful heated pool in SH
4.96 out of 5 average rating, 225 reviews
Luxury modern farmhouse with heated pool & hot tub
4.93 out of 5 average rating, 148 reviews
Stunning 3 bed 2 bath home W Pool
4.96 out of 5 average rating, 274 reviews
Oasis backyard, Pool, Gym, and Sunroom!
4.94 out of 5 average rating, 106 reviewsCondo rentals with a pool

Montauk Waterfront Condo w/ Sunset Views
5.0 out of 5 average rating, 261 reviews
Coastline View Studio
4.84 out of 5 average rating, 220 reviews
Beautiful Condo on the Ocean Bluffs
4.85 out of 5 average rating, 113 reviews
Beautiful condo on Long Islands Northfork
4.86 out of 5 average rating, 136 reviews
Waterfront Escape | Private Beach, Pool & Views
4.88 out of 5 average rating, 173 reviews
Beautiful Waterview Condo on the North Fork of LI
4.9 out of 5 average rating, 200 reviews
Sound Front Condominium
4.89 out of 5 average rating, 284 reviews
Montauk Royal Atlantic Beach Resort North
4.8 out of 5 average rating, 248 reviewsHome rentals with a private pool

Explore the Water & Woods at a Relaxing Retreat
4.98 out of 5 average rating, 148 reviews
Southampton Private House with Pool / Peaceful
4.91 out of 5 average rating, 74 reviewsEast Hampton Villa | Heated Saltwater Pool & Beach
4.91 out of 5 average rating, 116 reviewsEnchanting Home with Large Decks and Heated Pool
4.85 out of 5 average rating, 52 reviewsPerfect Getaway at Sunny Modern Shampton LakeHouse
4.96 out of 5 average rating, 25 reviewsSaltbox with Separate Poolhouse in Northwest Woods
5.0 out of 5 average rating, 13 reviewsDestinations to explore
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- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Fairfield Beach
- Ocean Beach Park
- Charlestown Beach
- Mystic Seaport Museum
- Mystic Aquarium
- Southampton Beach
- Sunken Meadow State Park
- Soundview Beach
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Wölffer Estate Vineyard
- Ocean Beach
- Sleeping Giant State Park
- Meschutt Beach
- Orient Beach State Park
- Ditch Plains Beach
- Wesleyan University
- Splish Splash Water Park
- Long Island Aquarium
- Stonington Vineyards





