Holiday rentals in The Hamptons

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

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.

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.

Stunning Central E. Hampton Home w/ gunite pool.

EH Registry #24-65. One of the top rentals in East Hampton, this beautifully remodeled 2,800 sq. ft. home is ideally located between East Hampton and Amagansett villages, close to beaches, dining and shopping. Features include 10' ceilings, a remodeled kitchen and baths, 4 bedrooms with new mattresses, dining for 10, beautiful landscaping, private fenced yard and large deck. Pool open mid-May–early Oct.; heat extra fee. NO PETS. No content creators, filming or commercial photography.

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.

Hamptons Waterfront Getaway – Stylish & Serene

Waterfront Luxury Retreat in Sag Harbor. As featured in Vogue, Mansion Global, and Homeworthy. This serene designer home offers direct bay access for kayaking and paddle boarding, plus a private path to Clam Island for peaceful walks and beach picnics. Enjoy a gourmet kitchen with Viking and Sub-Zero appliances, spa-like en-suite baths, and plush bedding. Minutes to bay beaches and Sag Harbor village—your private escape awaits. Ideal for romantic getaways, relaxing weeks, or a summer reset.

Serene East Hampton Escape - Warm Pool til Nov

A luxuriously curated woodland escape with massive pool (heated and open May through October), fully fenced and just minutes from EH Village & Ocean Beaches. This impeccably renovated four-bedroom, four-and-a-half-bath home offers refined comfort in a serene, private setting. Sunlight floods the expansive interiors, featuring rich luxurious finishes, a separate office with queen sofa bed, a freestanding soaking tub, and a designer chef’s kitchen with a custom dining table for ten or more.

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

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).

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.

Brand New Sun Filled Home

OUR HOUSE A beautiful newly renovated Southampton two story home with spectacular light, offering the best of indoor-outdoor living. A large deck off of the kitchen with small porches off of two primary suites and a small sitting area off the first floor junior suite. On almost one acre of land, there is plenty of peaceful space. Very central - two miles from the beach and town. Two car garage with built in electric vehicle charger. Gas fireplace. All appliances are brand new.

East Hampton Secluded Escape with Gunite Pool

Elegantly furnished 4 bedroom house on lushly landscaped grounds, fewer than 5 minutes from the heart of East Hampton Village. This home is ideal for outside living, featuring a gunite, in-ground salt-water pool and stone patio. The interior is bright and spacious, accented by minimalist yet warm furnishings. Common living areas include a large family room with TV, large dining room with gas fireplace, and a large eat in kitchen. Rental registry HMT23-10468