Villas and Holiday Homes in The Hamptons, NY

Centrally located in Greenport Village, this renovated barn conversion offers immediate walking access to local shops, restaurants, and the waterfront, with Fifth Street beach a convenient 9-block walk or short drive away.
This spacious 139 square meter holiday home accommodates up to six guests, boasting a fully renovated interior with a new washer/dryer, a fireplace, and a large, air-conditioned entertainment barn complete with a ping pong table and dart board, alongside a fenced backyard featuring an outdoor fireplace and Weber barbecue for al fresco dining.

Just under 3.2 kilometers from New Suffolk Beach and Veterans Beach, this Mattituck villa offers a tranquil getaway with easy access to McCall Wines and Pellegrini Vineyards, both located less than 1.6 kilometers away.
This family-friendly holiday home, accommodating up to 6 guests, boasts 134 square meters of living space including three bedrooms, two distinct living areas with fireplaces, a well-equipped kitchen, and a back deck perfect for sunset viewing and outdoor grilling, complemented by ample parking and a 1-car garage.

Centrally located in Westhampton Beach, this family-friendly villa is just a 5-minute walk to local restaurants, shops, and a farmer's market, and under 3.2 kilometres to Dune Road mansions and Rogers Beach, offering excellent proximity to family attractions like Splish Splash Water Park and the Riverhead Aquarium.
This spacious 279 square meter holiday home accommodates up to 10 guests with 5 bedrooms and 3 bathrooms, featuring a newly remodelled kitchen with a large quartz island, a heated 18x36 in-ground mountain pond pool, a hot tub seating 7, and a dedicated office space with gigabit WiFi, making it a perfect beach house rental.

South of the highway in Southampton, New York, this luxury townhouse offers an exclusive retreat just minutes from The Village and the Hamptons' premier beaches, providing a prime location for a sophisticated holiday home experience.
This exceptional villa rental boasts 149 square meters of living space, accommodating up to 6 guests with 2 bedrooms and 2 bathrooms, and features on-site amenities including tennis courts, multiple swimming pools, a putting range, and a gym, ensuring a wealth of leisure activities.

Located in Westhampton, this cottage offers a prime position just 1.5 kilometres from Moriches Bay and approximately 5 kilometres from the Westhampton Beach Performing Arts Center and The Great Lawn.
This villa provides a fully equipped kitchen with a microwave and dishwasher, air conditioning, an outdoor swimming pool, and complimentary Wi-Fi, making it an excellent holiday home for exploring the area, which includes attractions within 10 kilometres like Quogue Community Hall and Long Island Skydiving Centre.

Experience the Southampton Luxury Estate With Pool, Sunset Bay Views & Resort-style Backyard, a magnificent villa offering unparalleled resort-style living with expansive sunset views over Little Peconic Bay, located in a serene high-elevation setting in Southampton, just a short drive from boutique shops, galleries, restaurants, and ocean beaches.
This expansive 437 square meter holiday accommodation boasts grand designer interiors, a chef's kitchen, and comfortably accommodates up to ten guests in five bedrooms, featuring a private heated pool, gazebo, sundeck, and alfresco dining area within its exclusive resort-style backyard.

Perfectly situated on a historic Sag Harbor street, this luxury cottage offers prime walkability to the downtown core's shops, restaurants, and marinas, as well as the local beach, just 300 meters away. This welcoming villa rental provides two bedrooms accommodating up to four guests, featuring a designer kitchen, a private garden with a patio and outdoor shower, and extensive baby/toddler equipment for a family-friendly holiday home experience.

Just 300 meters from an expansive beach within a nature preserve, this East Hampton villa in the Springs district offers historic cedar shingle construction dating back to circa 1940, with wide pine floors and a unique fireplace. This welcoming holiday home, accommodating up to six guests, boasts modern amenities including a new Miele washer/dryer and internet, alongside direct access to a tandem kayak for exploring the coastline and enjoying incredible western sunsets.

Centrally located in East Hampton, this luxury villa rental offers proximity to historical sites such as the Pollock-Krasner House and Study Center and Old Hook Mill, with Kaplan Meadows Sanctuary and East Hampton Village Nature Trail and Wildlife Sanctuary a short distance away.
This spacious 4-bedroom, 4-bathroom holiday home comfortably accommodates up to 10 guests, boasting a resort-like backyard with a massive deck, swimming pool, hot tub, outdoor kitchen, and cabana with a fire pit, alongside modern amenities including an 85-inch smart TV and central air conditioning.

Located in Shinnecock Hills, this newly renovated designer villa is just a 5-minute drive from Cooper's Beach and Southampton Village, offering a prime holiday home experience.
This exclusive family-friendly property boasts a 32-foot heated salt water pool, a private garden with a BBQ grill, and ample parking, providing comfortable accommodation for up to 8 guests with high-speed Wi-Fi and air conditioning.

Villa Skylar, a spacious 7-bedroom villa rental, is located in Southampton, 48 kilometres from Hither Woods Preserve and Second House Museum.
This luxurious holiday home features a private swimming pool, Jacuzzi, tennis court, and a terrace with barbecue facilities, offering 446 square metres of accommodation with free WiFi and parking.

Located in Water Mill, Villa Xmart is 25.75 kilometres from Montauk Point Lighthouse and 67.59 kilometres from Long Island MacArthur Airport.
This spacious 279 square metre villa offers accommodation for up to 15 guests, featuring 5 bedrooms, a private swimming pool, an on-site bar, and a fully equipped kitchen, with car rental and room service available for convenience.

Offering serene views of Sagaponack's bird and wildlife sanctuary, this designer-decorated, post-and-beam cottage is located just 5 minutes from the LIRR and Hampton Jitney, providing easy access to Hamptons attractions like Wolffer Estate Vineyard.
This exclusive villa rental boasts a brand-new, private saltwater gunite pool, an open-plan ground floor flowing to an outdoor patio, and accommodates up to six guests, making it a perfect holiday home for exploring the local farm stands and beaches.

Located in East Hampton North, this contemporary apartment is just minutes from East Hampton village's shops and eateries, and a short bicycle ride to renowned beaches such as Two Mile Hollow, Egypt, and Wiborg.
This luxury villa rental boasts a 316 square meter floor area with an open-concept layout, accommodating up to eight guests with three ensuite bedrooms plus an additional sleeping space, and offers exceptional outdoor living with a heated gunite pool, hot tub, and a fitness centre.

Just a 3-5 minute walk from Long Beach, this Noyack apartment offers convenient access to Sag Harbor Village, a prime location for a holiday home.
This spacious 204 square meter villa rental accommodates up to 8 guests across 4 bedrooms and 3 bathrooms, boasting a heated saltwater swimming pool, a home theatre, and two living areas.

Centrally located in Laurel, this property is a 15-minute walk from Macari Vineyard and a 10-minute walk to Harbes Family Farm, offering convenient access to local vineyards and farms, with Hallock State Park Preserve and Laurel Lake Preserve nearby.
This spacious 102 square metre villa rental sleeps eight across four bedrooms, boasting a luxurious outdoor living area with a full outdoor kitchen and swimming pool (open mid-May to September 15), alongside indoor amenities including air conditioning, Wi-Fi, and a smart TV for an exceptional holiday home experience.

Villa Qadus in Southampton offers an exclusive retreat, situated just a 19-minute walk from Flying Point Beach and 20 kilometres from Montauk Point Lighthouse.
This expansive 8-bedroom villa rental, accommodating up to 31 guests, boasts a 743 square metre floor area and features a swimming pool, bar, fitness centre, and on-site mini-market, providing a comprehensive holiday home experience.

Conveniently located in Wainscott, this villa is situated 19 kilometres from Montauk Point Lighthouse and 29 kilometres from the Second House Museum, with Shadmoor State Park and Montauk Downs State Park Golf Course both 32 kilometres away.
This welcoming holiday home offers 325 square meters of air-conditioned living space, featuring two bedrooms and a terrace with garden views, ideal for up to 27 guests.

Centrally located in Hampton Bays, this villa is just 2 minutes by car from bay beaches and 10 minutes from ocean beaches, offering convenient access to the North Main Street Historic District and Halsey House.
This spacious holiday home accommodates 10 guests with 5 bedrooms and 4 bathrooms, featuring a heated outdoor swimming pool available from May to September and an outdoor living room with garden and woods views.

Offering direct waterfront access to an inlet leading to Peconic Bay, this Hampton Bays cottage is just a short distance from Splish Splash Water Park.
This 70 square meter villa rental, accommodating up to 4 guests in 2 bedrooms, boasts a private deck with BBQ, shared access to a 300-meter walking dock, and complimentary use of kayaks, canoes, and bicycles, providing a welcoming holiday home experience.