These Hamptons Vacation Rentals Are Worth Booking for the Pool Alone

The Hamptons have long been one of the East Coast ’s ultimate summer escapes . But while the region’s storied hotels have their allure, some of its most memorable stays, and swimming pools, are tucked behind the hedges of beautifully designed vacation homes, where sprawling lawns, cedar-shingled architecture, and resort-worthy backyards make lingering all day part of the itinerary.

Whether you’re planning a family getaway , a friends’ weekend , or simply searching for a vacation rental with a pool in the Hamptons that feels worlds away from the city, the right stay has the potential to make or break your trip. As a Long Islander who spent most of her summers out east, I know vacation rentals in this area aren’t always the easiest to find. Some book up extra early, and others have strict requirements that ask a lot of the guests. To help you out with your next glitzy Hamptons stay, I've found these properties, from Airbnb , Vrbo , Plum Guide , Marriott Homes & Villas , and more, that offer the best amenities, the swankiest design, and of course, absolutely stellar pools to dive into. Picture heated saltwater pools framed by hydrangeas, sleek modern retreats with infinity-edge swims , and classic estates with morning laps followed by dinners beneath the stars . Read on for my favorite Hamptons vacation rentals with pools to enjoy this summer.

We've selected these listings based on Superhost and Guest Favorite status, editor stays, ratings, amenities, location, decor, and previous guest reviews.

Number of guests: 8 Bed and bath: 4 bedrooms, 3 baths Why we love it: Heated pool, bluestone patio, fenced yard, outdoor dining with barbecue grill, two living rooms, fireplace

Set in a quiet residential pocket of Southampton, this single-level home is as chic and stylish as it is practical. Sliding glass doors open onto a bluestone patio where the pool, dining table, sun loungers, and grill are all arranged. Inside, the house is split into two living rooms, one is a bit more formal and centered around a fireplace, while the other is set up for casual gatherings and movie nights. The kitchen sits between them with stainless steel appliances, an island with stools, and a dining table for six. The fenced yard and amenities galore, plush chaise chairs, a sparkling heated pool, a wooden deck for alfresco dinners, make the property great for families. It’s also close to some less-crowded beaches and the charming town center.

City: Southampton Things to do nearby: Cooper’s Beach, Gin Lane, Parrish Art Museum, Village Center with restaurants and shops

Number of guests: 8 Bed and bath: 5 bedrooms, 3.5 baths Why we love it: Garden views, smart TV, pool toys, outdoor furniture, pool table, indoor fireplace

This is a three-level Sag Harbor house built for group stays where guests can split up during the day for some alone time. The main level has an open kitchen, dining area, and living room that all face a central courtyard with a pool and outdoor seating just outside the sliding doors. It’s the main hub of the house, especially for meals and quick dips between beach runs. The middle floor is the most functional for groups: There are two separate entertainment rooms, each with its own wet bar and lounge setup. One works easily as a TV and game room, while the other functions more as a space for drinks and conversation. Downstairs, there’s a fifth bedroom with an en suite bathroom plus a dedicated office, which is useful for guests who need a quieter setup or are working remotely. Outside, a grill and firepit area sit off the main courtyard for simple dinners and late-night hangouts. It’s best for two families traveling together, or friend groups who want shared spaces without shared schedules.

City: Sag Harbor Things to do nearby: Sag Harbor Village, Havens Beach, Long Wharf, Bay Street Theater, Mashashimuet Park

Number of guests: 8 Bed and bath: 4 bedrooms, 2 baths Why we love it: Concierge, washer and dryer, heated pool, outdoor furniture, professional cleaning service upon request

This straightforward Southampton house is best for families or friend groups who want a reliable base close to beaches and village life. Inside, you'll find an open main level that encompasses the kitchen, dining, and living space, with a fireplace, hardwood floors, and lots of seating for cozying up during movie or game nights. Sliding doors open directly onto a bluestone patio where a heated pool, a hot tub, a firepit, a dining table, and lounge seating are available. Everything sits within the fenced-in backyard, and concierge and optional cleaning services make it simple for longer stays, especially for repeat summer use.

City: Southampton Things to do nearby: Cooper’s Beach, Southampton Village, Parrish Art Museum, Southampton Arts Center, Shinnecock Hills

Number of guests: 7 Bed and bath: 3 bedrooms, 3.5 baths Why we love it: Outdoor firepits, pet-friendly, library of books and board games, proximity to the beach

Look out for artists , poets, and musicians in the area around this home, it’s located in Springs, arguably one of the coolest towns in the Hamptons. The home sits on 1.5 acres that open into a lawn, trees, and a pool terrace at the back. Don't get me started on its outdoor setup, it's complete with a heated pool framed by plush loungers, a shaded dining area under wisteria, and firepits positioned for evening use. Inside, rooms are filled with patterned textiles, eclectic artwork, and mismatched furniture that give each space a cool, unique feel. A library of books and board games is set up for downtime between beach trips. The location puts you close to Accabonac Harbor, local surf beaches , and just a short bike ride from the ocean. Springs's Saturday farmers market is also nearby, along with East Hampton Village for dining and shopping.

City: East Hampton (Springs) Things to do nearby: Springs Farmers Market, Accabonac Harbor, Main Beach, Amagansett Dunes, East Hampton Village

Number of guests: 10 Bed and bath: 5 bedrooms, 3.5 baths Why we love it: Pet-friendly, sprawling outdoor pool area, outdoor table with umbrella, fully equipped kitchen

Set on more than an acre of land beside the Long Pond Greenbelt, this Bridgehampton home has a backyard that gets direct sun from morning through late afternoon. A heated in-ground pool sits at the center, framed by nine loungers, four umbrellas, an outdoor shower, and a separate pool house that makes long pool days feel fully self-contained. The outdoor dining area is anchored by a long teak table for 12, positioned just off the pool deck, so alfresco meals, grilling, and lounging all happen within the same stretch of space. Inside, the size is generous in traditional Hamptons style: a cathedral-ceiling living room, breakfast room, dining area, and a newly renovated chef’s kitchen with Sub-Zero, Wolf , and Cove appliances. The primary king suite sits on the main level, with four additional bedrooms upstairs (three queens and a room with two single beds), making it especially suited for multi-family or friend group stays that want separation come nightfall but days filled with shared time outside.

City: Bridgehampton Things to do nearby: Long Pond Greenbelt, Sag Harbor Village, Bridgehampton Village, Wölffer Estate Vineyard, Mecox Beach

Number of guests: 6 Bed and bath: 4 bedrooms, 4 baths Why we love it: Two wood-burning stoves, outdoor dining, heated pool, chef’s kitchen

Just minutes from ever-charming East Hampton Village, this midcentury home is set deep in dense East Hampton woodland. The design makes the space feel carved into the trees, with glass walls that pull the green canopy into every room, and sunlight that moves cleanly across wide, open interiors. The main living space leans warm and tactile, with an olive-green sofa, layered and colorful textiles, velvet accents, and bold artwork that gives the house a real design-forward feel. The layout is centered around a fireplace and flows through the large kitchen, dining, and lounge spaces, each framed by high ceilings and oversized windows. Here, you and your squad are promised mornings with coffee at the counter, and afternoons reading on the sofa, followed by easy dips in the sparkling heated pool outside.

City: East Hampton Things to do nearby: East Hampton Village, Bay Beaches, Main Beach, LongHouse Reserve, Amagansett Main Street

Number of guests: 14 Bed and bath: 7 bedrooms, 8.5 baths Why we love it: Spacious grounds and interiors, at-home gym, red light studio, hot tub, outdoor movie theater, firepits, games

This nine-acre Sag Harbor estate (near Sagaponack) just might have it all. You’ll be welcomed in by a long driveway, then a koi pond and tennis court, as well as a gradual reveal of the lawn and pool. The outdoor setup is all yours, and it’s extensive: a 55-foot heated infinity-edge pool with a waterfall, a cedar soaking tub for 12, firepits arranged for large groups, and an outdoor movie screen set up across the backyard. There are multiple grilling stations and long tables designed for communal dining. Inside, the house leans more modern-rustic with reclaimed wood floors, antique decor, and a layout built for fun-filled group stays, complete with a media lounge, billiard room, gym, and red light studio, with smart TVs throughout.

City: Sag Harbor Things to do nearby: Sag Harbor Village, Long Wharf, Havens Beach, Bay Street Theater, Wölffer Estate Vineyard

Number of guests: 12 Bed and bath: 5 bedrooms, 3.5 baths Why we love it: Heated saltwater pool, outdoor shower, kayaks, paddleboards, beach toys and cruisers, in-ground hot tub

This oasis is entirely about the water, with the upper floor acting as one continuous living space, flowing through the kitchen, dining room, and lounge, that all opens onto a long deck that runs along the bay-facing side of the home. The connection between indoors and outdoors is seamless thanks to sliding doors that can stay open most of the day, and the deck is set up for both dining and lounging, perfect for before and after dips in the pool. Down below, the heated saltwater pool and in-ground hot tub sit on a mahogany deck with loungers and shaded seating. A lawn leads toward Swan Pond, and a private path reaches the beach in a few minutes. Everything needed for a stay is already on-site, bikes , kayaks, paddleboards, beach chairs, so all your time will oscillate between beach, deck, and pool, just as a classic Hamptons trip intends.

City: East Hampton Things to do nearby: Main Beach, Georgica Beach, East Hampton Village, Guild Hall, LongHouse Reserve

Number of guests: 10 Bed and bath: 5 bedrooms, 4.5 baths Why we love it: Outdoor barbecue area with furniture, indoor fireplace, sound system, fully equipped kitchen

This is a Water Mill house that makes summer feel immediately uncomplicated, where mornings start in a real chef’s kitchen with Sub-Zero and Bosch appliances and drift straight into pool time with Sonos sound systems already running music through the house. The heated gunite pool is the star of the show, with loungers, shaded corners, and enough space around it that groups can naturally spread out. Come the late afternoon, the firepit becomes the reset point before the barbecue and outdoor dining table take over for long, unfussy dinners. Not to mention, the home’s marble bathrooms keep the whole stay feeling clean and elevated after sandy, saltwater days. It’s best for families or friend groups who want a base in quaint Water Mill, a place that smoothly handles everything: food, swimming, and downtime, without needing to overly organize your experience around it.

City: Water Mill Things to do nearby: Cooper’s Beach, Shinnecock Hills Golf Course, South Fork Natural History Museum, Bridgehampton Village, Water Mill Farms