
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.

Serene, chic private house near best attractions!
Escape to your serene, chic, Hamptons oasis! Cuddle up at the wood-burning fireplace with nature views all around the house. Enjoy your cozy bedrooms, fully stocked Chef's kitchen + 80' streaming TV. You may see deer and bunnies around the property! Toast marshmallows around the firepit + spark up the BBQ under the starry sky. A perfect escape for you to reset! You will be 8 minutes to Main St of East Hampton + Amagansett. Near coffee shops, restaurants, beaches, pumpkin/apple picking + more!
4.9 out of 5 average rating, 144 reviews
Sprawling Hamptons Estate with Hot Tub & Amenities
Spacious & private Hamptons Oasis. High speed WiFi. Family friendly. Massive home on 1.4 acres hosts 15 guests across 6 bedrooms, 8 beds, 4 full baths plus crib & pack 'n play. Gorgeously decorated by Judy Posey Large heated gunite pool (42 x 20 feet) hot tub and sundeck. Fireplace, over-sized kitchen w/ 3 fridges, electric wood-fired grill, huge yard, firepit, bar/lounge, Golden Tee arcade™, bikes & kayaks. Just 2 miles from towns of East Hampton and Amagansett and several white sand beaches
4.78 out of 5 average rating, 146 reviews
Southampton Charmer, 5 bedrooms w pool - Location
This 5-bedroom home boasts en-suite baths and elegant furnishings. The gourmet kitchen features marble countertops and stainless steel appliances, leading to a dining area. The lower level includes a spacious seating area and a game room with toys. The second floor houses a master suite with stunning views and three additional en-suite bedrooms. Located minutes from the village center, with restaurants, shops, and beaches nearby. A heated pool invites you to relax and enjoy the comfort of home.
4.93 out of 5 average rating, 139 reviews
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 Cozy Cape - 5 min 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.
4.98 out of 5 average rating, 160 reviews
East Hampton Escape | Heated Pool + Outdoor Living
Escape to a 5* rated Hamptons retreat designed for effortless summer living. Set on a quiet property surrounded by mature landscapes, this light-filled designer home offers the perfect balance of privacy, comfort, and indoor-outdoor flow. The open concept layout is filled with natural light, feat a modern kitchen, multiple living areas, and thoughtfully designed bedrooms for a relaxed, and comfortable stay. Ideal for small groups looking for elevated escape minutes from beaches and town.
4.99 out of 5 average rating, 126 reviews
Hamptons Oasis: pool, grill, lush landscape
Kick back and relax in this calm, stylish, contemporary masterpiece. 4 beds, 3 baths, eco pool, and expansive outdoor living space. Architecturally impressive structure surrounded by lush landscape and tastefully decorated. The outdoor space includes a pool, a new outdoor grill, a fire pit, pool lounge chairs, a dining table under a wisteria pergola and an outdoor sofa area big enough to fit your entire party. Fully equipped kitchen. Short drive to the beach and to downtown Westhampton.
4.95 out of 5 average rating, 146 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
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
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
Central Private Bridgehampton Home
4.93 out of 5 average rating, 109 reviews
East Hampton Home: Heated Pool, Gym, Fully Fenced
4.97 out of 5 average rating, 112 reviews
East Hampton Oasis - Pool and Hot Tub
4.83 out of 5 average rating, 144 reviews
Luxury modern farmhouse with heated pool & hot tub
4.92 out of 5 average rating, 149 reviews
Hampton's Haven
4.93 out of 5 average rating, 167 reviews
Oasis backyard, Pool, Gym, and Sunroom!
4.94 out of 5 average rating, 107 reviews
East Hampton Secluded Escape with Gunite Pool
4.89 out of 5 average rating, 70 reviewsCondo rentals with a pool

Montauk Waterfront Condo w/ Sunset Views
5.0 out of 5 average rating, 262 reviews
Beautiful Condo on the Ocean Bluffs
4.85 out of 5 average rating, 113 reviews
Coastline View Studio
4.84 out of 5 average rating, 221 reviews
Sound Front Condominium
4.89 out of 5 average rating, 284 reviews
Waterfront Escape | Private Beach, Pool & Views
4.85 out of 5 average rating, 177 reviews
Beautiful Waterview Condo on the North Fork of LI
4.9 out of 5 average rating, 200 reviews
Beautiful condo on Long Islands Northfork
4.86 out of 5 average rating, 136 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 reviews
Chic Poolside Hideaway in East Hampton
4.89 out of 5 average rating, 38 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





