The Hamptons’ Best-Kept Secrets: Vacation Rentals with Pools
The Hamptons have long been a favorite summer destination for those seeking a tranquil retreat from the hustle and bustle of city life. While the region’s storied hotels offer a sense of luxury and charm, some of the most memorable stays are often found in beautifully designed vacation homes, boasting sprawling lawns, cedar-shingled architecture, and resort-worthy backyards that make lingering all day a must.
Source: media.cntraveler.com
As a seasoned Long Islander, I’ve spent countless summers exploring the East Coast’s ultimate summer escapes, and I’m here to share my top picks for the most unforgettable Hamptons vacation rentals with pools. Whether you’re planning a family getaway, a friends’ weekend, or simply seeking a relaxing retreat, these properties promise to make your stay truly unforgettable.
Source: media.cntraveler.com
Paradisical Base in Southampton
Set in a quiet residential pocket of Southampton, this stunning single-level home is the epitome of chic and stylish living. The property boasts a heated pool, a bluestone patio, and a fenced yard, perfect for families seeking a safe and relaxing environment. Inside, the house is split into two living rooms, one formal and centered around a fireplace, while the other is set up for casual gatherings and movie nights. The kitchen is a haven for culinary enthusiasts, with stainless steel appliances, an island with stools, and a dining table for six.
Source: media.cntraveler.com
The fenced yard and amenities galore, including plush chaise chairs, a sparkling heated pool, and a wooden deck for alfresco dinners, make this property an ideal choice for families. It’s also close to some less-crowded beaches and the charming town center, offering the perfect blend of relaxation and exploration.
Modern Stunner in Sag Harbor
This three-level Sag Harbor house is a haven for group stays, offering a central courtyard with a pool and outdoor seating just outside the sliding doors. The main level features an open kitchen, dining area, and living room, perfect for meals and quick dips between beach runs. The middle floor is the most functional for groups, with two separate entertainment rooms, each with its own wet bar and lounge setup.
Downstairs, there’s a fifth bedroom with an en-suite bathroom plus a dedicated office, ideal for guests who need a quieter setup or are working remotely. Outside, a grill and firepit area sit off the main courtyard, perfect for simple dinners and late-night hangouts. This property is best suited for two families traveling together or friend groups seeking shared spaces without shared schedules.
Spruced-Up Southampton Stay
This straightforward Southampton house is perfect for families or friend groups seeking a reliable base close to beaches and village life. Inside, the open main level encompasses the kitchen, dining, and living space, with a fireplace, hardwood floors, and plenty 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. The fenced-in backyard and concierge services make it simple for longer stays, especially for repeat summer use. This property is an excellent choice for those seeking a hassle-free and relaxing Hamptons vacation.
