Villas and Vaction Homes in The Hamptons, NY

Directly on 365 feet of Peconic Bay waterfront, this Aquebogue cottage offers a welcoming holiday home experience on the North Fork of Long Island, just minutes by car from over 40 wineries in Long Island's Wine Country.
This pet-friendly, family-friendly cottage boasts 550 square feet of living space with 2 bedrooms and 1 bathroom, accommodating up to 5 guests, and includes complimentary kayaks, paddle boards, and canoes for exploring the bay, alongside a screened-in porch and outdoor shower for ultimate relaxation.

Directly on Three Mile Harbor in East Hampton, this 2-bedroom cottage offers spectacular sunset views and waterfront access, sitting adjacent to a golf course and a short drive to Napeague State Park.
This private, stand-alone villa, known as 'The Ritz', provides complimentary use of kayaks, access to a tennis court and golf practice facility, and features a newly renovated interior with central air conditioning, making it an ideal holiday home for up to 4 guests.

Located in Hampton Bays, this vacation home is situated 15 miles from Splish Splash, 30 miles from Montauk Point Lighthouse, and 11 miles from Agawam Park.
This spacious 4-bedroom villa offers a private pool, year-round jacuzzi, outdoor fireplace, and a fitness center, accommodating up to 15 guests with 2200 square feet of living space.

Located within the Shinnecock Bay Club in Hampton Bays, this villa is just 1 mile from Ponquogue Beach and minutes from Tiana and Meschutt Beaches, offering convenient access to both the North and South Forks of the East End.
This welcoming holiday home features a fully renovated interior with brand new furnishings, a fully equipped kitchen, and a private sitting area with a grill, accommodating up to 4 guests with a dedicated parking space.

Offering unparalleled water views, this Southold cottage is a mere 5-minute walk to the Long Island Sound with full beach access, placing you minutes from award-winning wineries and local attractions like Horton Point Park.
This family-friendly villa, boasting 1500 square feet of living space and a guest capacity of 5, features 3 bedrooms, a full-sized bedroom loft, a kitchen with a dishwasher and microwave, air conditioning, a swimming pool, a garden, and a spa for a complete holiday home experience.

Located on a peaceful road in Shelter Island, this apartment is within walking distance to the main town, recreational facilities, and natural attractions including Wades Beach and Fresh Pond.
This welcoming family-friendly holiday home offers 3 bedrooms and accommodates up to 6 guests, featuring central air conditioning, a kitchen with a fridge, microwave, and dishwasher, and a private outdoor living space with a deck, barbecue, and enclosed outdoor shower, plus provided beach essentials for your convenience.

This exclusive villa is located near Big Fresh Pond, an 8-minute drive from Southampton Village, offering proximity to Ocean Beaches.
Enjoy a private deck with garden and pool views, a heated saltwater pool (seasonally available), a year-round hot tub, outdoor fire pit, and private dock access on Big Fresh Pond for paddle boarding and kayaking.

Located in a rural waterfront area of Southold, this welcoming villa is just six blocks from Kenney's Beach on the Long Island Sound and a short drive to the village and 20 North Fork wineries.
Offering 800 square feet of living space, this family-friendly apartment accommodates up to four guests with two bedrooms, a ranch-style kitchen, air conditioning, and WiFi, while the half-acre property boasts a private bulkheaded lakefront perfect for swimming, fishing, and kayaking.

Book this vacation rental for 4 guests with an excellent rating of 100% based on 2 reviews. You will be located in Hampton Bays.
Services and facilities include a kitchen, a washing machine and a barbecue. Take advantage of the air conditioning in this apartment!

Just 100 steps from a private beach in Riverhead, this welcoming beach house offers exclusive access to the shore with provided chairs, towels, and an umbrella, making it a perfect holiday home.
This luxurious 3-bedroom, 2-bathroom villa accommodates up to 8 guests and features an open-concept great room with a 65” Smart HDTV, a fully equipped kitchen with brand new appliances, and outdoor amenities including a Weber gas grill, all within easy reach of local vineyards and family-friendly attractions.

Villa Lalam in Southampton offers a prime location, just 24 miles from Montauk Point Lighthouse and 29 miles from the Second House Museum, placing you near notable historical sites and the natural beauty of Shinnecock Hills.
This expansive villa provides 2500 square feet of living space with 5 bedrooms and 1 bathroom, featuring a private swimming pool, jacuzzi, terrace, garden, and an on-site bar, all complemented by air conditioning and free WiFi for a comfortable stay.

Enjoy a recently renovated 3-bedroom, 2-bathroom apartment in Noyack, Sag Harbor, offering a tranquil escape just minutes from pristine bay and ocean beaches, marinas, nature preserves, dining, and shopping.
This welcoming holiday home boasts a sun-filled kitchen and dining area, a light and airy sunroom, and a beautifully landscaped private garden with a bluestone patio and picturesque pergola, perfect for outdoor enjoyment and accommodating up to 6 guests.

This welcoming villa in Springs offers exclusive access to a private outdoor shower and a spacious backyard, ideal for couples or two single guests seeking a relaxing retreat.
Guests will enjoy convenient access to local amenities and attractions in Springs, with a fitness center and swimming pool available for use, alongside a fully equipped kitchen and air conditioning for ultimate comfort.

This luxurious villa is located in Southampton, just 1.5 miles from Flying Point Beach, offering a prime location for your next holiday home escape.
With 6 bedrooms accommodating up to 27 guests, this spacious villa boasts a private swimming pool, sauna, fitness center, and a terrace with lake views, ensuring a comfortable and amenity-rich stay.

This Hampton Bays cottage, located in a quiet neighborhood, offers convenient access to Meschutt Beach, just 3 miles away, and is 8 miles from Southampton Village for upscale shopping and dining.
This welcoming holiday home, perfect for up to 6 guests, features a fully equipped kitchen, a seasonal swimming pool, a trampoline, a fire pit, an outdoor shower, and an EV charger, providing ample entertainment and comfort during your stay.

This Sag Harbor retreat is located in Noyack, offering convenient access to Long Beach, just a 4-minute drive away, and Sag Harbor Village, a 7-minute drive for dining and exploration.
Enjoy exclusive use of a private saltwater pool and a spacious outdoor living area with a fire pit and dining, making this a welcoming holiday home perfect for up to 6 guests.

Centrally located in East Hampton, this luxurious villa offers convenient access to local attractions and is easily reachable by train or car, with on-site automobile parking provided.
This welcoming holiday home features 4 bedrooms, accommodates up to 10 guests, and boasts a custom saltwater heated pool with a shallow area and lap lane, alongside a built-in bar/media room for adult relaxation.

Located in Sagaponack, this villa is 14 miles from Montauk Point Lighthouse and 19 miles from Second House Museum, with Shadmoor State Park 21 miles away.
This welcoming holiday home features air conditioning, a swimming pool, a terrace with garden views, and accommodates up to 16 guests with a fully equipped kitchen and free WiFi.

Architecturally unique, this modern beach house is located in East Hampton's Settlers Landing neighborhood, a short drive from East Hampton Village, Sag Harbor, and Amagansett, and close to Sammy's Beach.
Offering 1700 square feet of living space, this 5-bedroom villa accommodates up to 10 guests and features a free-form heated pool, a new 7-person hot tub, vaulted ceilings, an open-concept living space with a wood-burning fireplace, and two spacious balconies, making it an ideal holiday home for exploring water adventures and hiking trails.

Located in Southampton, this luxury villa is situated 18 miles from Splish Splash and 24 miles from Montauk Point Lighthouse, offering a prime destination for exploring Shinnecock Hills.
This 5-bedroom holiday home boasts 3300 square feet of living space, accommodating up to 19 guests with amenities including a private swimming pool, jacuzzi, air conditioning, Wi-Fi, and an on-site bar.