Villas and Holiday Homes in The Hamptons, NY

22592 Villas and Holiday Homes in The Hamptons, NY

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The Hamptons, NY
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Best villa offers in The Hamptons, NY

Villas and holiday homes with private pool in The Hamptons

At the heart of Long Island's most sought-after retreat, our holiday homes with pool in the Hamptons include heated pools and infinity options.

Hamptons Vacation Rental W/ Saltwater Pool - The Hamptons, NY
9.8 7 reviews

Hamptons Vacation Rental W/ Saltwater Pool

cottage, Hampton Bays
Located in Hampton Bays, this cottage is situated in a peaceful neighbourhood, approximately 4.8 kilometres from Meschutt Beach and within easy reach of Southampton's attractions.
This welcoming villa rental, offering 103 square metres of living space for up to six guests, boasts a fully equipped kitchen, a seasonal swimming pool, a trampoline, and a fire pit, alongside an EV charger for convenience.
East Hampton Villa | Heated Saltwater Pool & Beach - The Hamptons, NY
9.8 113 reviews

East Hampton Villa | Heated Saltwater Pool & Beach

house, Springs
Exclusive walking access to private Clearwater Beach, just 300 meters away, is offered by this East Hampton bungalow, a twelve-minute drive from the renowned restaurants of East Hampton village.
This luxurious villa rental boasts four bedrooms accommodating up to six guests, featuring a heated saltwater swimming pool set within professionally landscaped grounds, a chef's kitchen, and a primary suite with a marbled ensuite and claw-foot soaking tub, perfect for a family holiday home.
Southampton 2 Bedroom 2.5 Bath Townhome - The Hamptons, NY
10 1 review

Southampton 2 Bedroom 2.5 Bath Townhome

house, Tuckahoe
Located in Tuckahoe, this delightful villa rental is situated within a private condo development, offering convenient access to Southampton Village centre, just 1.5 kilometres away, and the beautiful Coopers Beaches, a mere 2 kilometres distant.
This welcoming holiday home boasts two bedrooms and two bathrooms, accommodating up to four guests, and features a fully equipped kitchen, high-speed internet, a dedicated workspace, and a landscaped patio, alongside shared amenities including swimming pools, tennis courts, and a gym within the development.
Southampton Beauty - The Hamptons, NY
No reviews

Southampton Beauty

house, Shinnecock Hills
Located in the exclusive Shinnecock Hills, this Southampton holiday home is situated 29 kilometres from Splish Splash and 39 kilometres from Montauk Point Lighthouse.
Boasting 271 square meters of floor area, this villa offers spacious accommodation for up to 15 guests with 4 bedrooms and 3 bathrooms, complemented by an outdoor swimming pool, a terrace, and a garden for your enjoyment.

Villas and holiday homes by the sea in The Hamptons: sea view and coastal stays

Browse our holiday homes by the sea in the Hamptons: some properties offer direct Atlantic beach access along Long Island's most sought-after shoreline.

Waterfront Cottage In The Hamptons - The Hamptons, NY
10 3 reviews

Waterfront Cottage In The Hamptons

house, Shinnecock Hills
Offering direct waterfront access to a private lagoon and set within over an acre of landscaped grounds, this exclusive Southampton villa rental is situated in the tranquil Shinnecock Hills, a prime location for enjoying the natural beauty of the Hamptons. This welcoming holiday home boasts 3 bedrooms, accommodating up to 6 guests, and features a fully equipped kitchen, air conditioning, and a garden, with the added benefit of being pet-friendly for a complete seaside retreat.
Villa Perlman - The Hamptons, NY
9.9 33 reviews

Villa Perlman

house, Shinnecock Hills
Villa Perlman in Southampton offers a luxurious 5-bedroom villa experience, situated 29 kilometres from Splish Splash and 42 kilometres from Montauk Point Lighthouse.
This spacious holiday home boasts a private swimming pool, a Jacuzzi, a garden, and a terrace, alongside a well-equipped kitchen featuring a fridge, microwave, and dishwasher, with complimentary WiFi and parking provided.
Beachfront Greenport Villa - The Hamptons, NY
10 1 review

Beachfront Greenport Villa

house, Southold
Directly on the beach in Greenport, this villa is conveniently located 35 kilometers from Splish Splash water park and 22 kilometers from the Long Island Railroad.
This spacious holiday home accommodates up to 15 guests with 3 bedrooms and 3 bathrooms, offering air conditioning, a fully equipped kitchen, complimentary WiFi, and private parking for a comfortable stay.
4th Of 6 Premier Waterfront Vacation Rentals On Long Island Ny In Wine Country Of Famed North Fork - The Hamptons, NY
9.8 19 reviews

4th Of 6 Premier Waterfront Vacation Rentals On Long Island Ny In Wine Country Of Famed North Fork

cottage, Aquebogue
Directly on 114 meters of Peconic Bay shoreline, this Aquebogue cottage offers exclusive waterfront access and complimentary kayaks, paddle boards, and canoes for exploring the bay, whilst also providing free beach passes to five local town beaches and being centrally located within Long Island's Wine Country.
This welcoming holiday home, a 51 square metre villa rental, accommodates up to five guests across two bedrooms and one bathroom, featuring air conditioning, a kitchen with a fridge and microwave, parking, and a screened-in porch perfect for enjoying the surrounding local shops, farm stands, and fine dining establishments.

Frequently Asked Questions about The Hamptons, NY

  • What are the must-see attractions that I should visit in The Hamptons, NY?

    When visiting The Hamptons, a stop at the Parrish Art Museum in Water Mill is essential for its impressive collection of American art. For a classic Hamptons experience, Montauk Point State Park offers stunning ocean views and a historic lighthouse. Southampton Village also boasts beautiful beaches like Coopers Beach and the historic Southampton Historical Museum.
  • How much does it typically cost to stay in a villa in The Hamptons, NY?

    Villa rental prices in The Hamptons vary significantly based on location, size, amenities, and the time of year. During peak season, which is typically from Memorial Day through Labor Day, expect prices to range from approximately $20,000 to over $100,000 per month. Off-season rentals can be considerably less expensive, sometimes falling between $5,000 and $20,000 per month.
  • What are the best towns, villages, or areas to rent a villa in The Hamptons, NY?

    For a quintessential Hamptons experience, consider renting a villa in Southampton, known for its elegant estates and pristine beaches. East Hampton offers a sophisticated atmosphere with beautiful oceanfront properties and a vibrant village center. For a more relaxed and rustic feel, Montauk provides stunning natural beauty and waterfront access. Sag Harbor, with its historic maritime charm, is another popular choice.
  • When is the best time to book a villa in The Hamptons, NY, and how far in advance should I plan?

    The peak rental season for villas in The Hamptons runs from late May through early September. To secure the best properties, especially for popular areas like East Hampton or Southampton, booking should ideally be done six to twelve months in advance. For shoulder seasons, like late spring or early fall, booking three to six months ahead is generally advisable.
  • What are the must-see festivals or seasonal events in The Hamptons, NY?

    The Hamptons hosts several notable events throughout the year. The Hampton Classic Horse Show in Bridgehampton is a major equestrian event held in late August. During the summer, the Hamptons International Film Festival draws filmmakers and enthusiasts. The East Hampton Antiques Show, usually held in July, is another significant draw for collectors.

Villas in Popular Destinations

Luxury villas and holiday homes in The Hamptons

Our curated luxury holiday homes in the Hamptons include some of Long Island's most sought-after properties. Find your luxury holiday home.

Villa Ebrar - Luxury With Pool - The Hamptons, NY
No reviews

Villa Ebrar - Luxury With Pool

house, Noyack
Villa Ebrar is a welcoming villa located in Sag Harbor, offering convenient access to Foster Memorial Beach, just 3.1 kilometres away, and is 32.2 kilometres from Montauk Point Lighthouse.
This spacious holiday home boasts 279 square metres of living space with four bedrooms and three bathrooms, accommodating up to 15 guests, and features a dishwasher, air conditioning, swimming pool, terrace, garden, and an on-site bar for your enjoyment.
Villa Spectrum Luxury Villa With Pool & Outdoor Shower In East Hampton - The Hamptons, NY
1.0 1 review

Villa Spectrum Luxury Villa With Pool & Outdoor Shower In East Hampton

house, Springs
Villa Spectrum is located in Springs, 7.8 miles from Montauk Point Lighthouse and 13 miles from Second House Museum.
This welcoming villa offers 218 square meters of living space, accommodating up to 7 guests with two air-conditioned bedrooms, two bathrooms, a fully equipped kitchen, and a private swimming pool with sun terrace, complemented by on-site bike and car rental services perfect for exploring the surrounding cycling and hiking trails.
Villa Qadus - Luxury With Pool - The Hamptons, NY
No reviews

Villa Qadus - Luxury With Pool

house, Southampton
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.
Villa Zainip - Luxury With Pool - The Hamptons, NY
No reviews

Villa Zainip - Luxury With Pool

house, Noyack
Villa Zainip in Sag Harbor offers a luxurious escape, situated 33.7 kilometres from Montauk Point Lighthouse and 41.8 kilometres from Splish Splash.
This expansive 279 square metre villa rental boasts 5 bedrooms, accommodating up to 15 guests with amenities including a private swimming pool, sauna, bar, and garden, alongside complimentary Wi-Fi and parking.

Villas and family holiday home rentals in The Hamptons

Our selection of family holiday homes in the Hamptons features properties with large gardens and gated pools. Browse our family-friendly holiday rentals.

Villa Gavin - The Hamptons, NY
No reviews

Villa Gavin

house, Southampton
Villa Gavin, a luxurious villa rental, is located in Southampton, offering convenient access to Splish Splash (32 kilometres) and Montauk Point Lighthouse (37 kilometres).
This welcoming holiday home boasts a floor area of 176 square meters, accommodating up to 18 guests with 3 bedrooms, a fully equipped kitchen, air conditioning, a swimming pool, and a terrace, alongside barbecue facilities and a paid airport shuttle service.
Villa Montauk Mist - The Hamptons, NY
No reviews

Villa Montauk Mist

house, Northwest Harbor
Villa Montauk Mist, a luxurious villa rental in East Hampton, is located 17.7 kilometres from Montauk Point Lighthouse and 27.4 kilometres from the historic Second House Museum.
This spacious 325 square metre holiday home comfortably accommodates 15 guests with 4 bedrooms and 3 bathrooms, featuring a private swimming pool, a patio with an outdoor fireplace, and complimentary WiFi.
Live On The Water: Dock, Beach, Boat, Kayak & Fish - The Hamptons, NY
10 110 reviews

Live On The Water: Dock, Beach, Boat, Kayak & Fish

house, North Sea
Located in Southampton Cove, this family-friendly waterfront property is just one kilometre from the beach and offers convenient access to Southampton Village and Sag Harbour.
This luxurious villa rental boasts four bedrooms, accommodating up to nine guests, and features a private dock, expansive garden with a fire pit and Weber grill, smart home technology, and a kids' playroom, making it a premier holiday home for watersports and outdoor activities.
Villa Mist Manor - The Hamptons, NY
No reviews

Villa Mist Manor

house, East Hampton
Villa Mist Manor, a spacious 5-bedroom villa, is located in East Hampton, offering proximity to Montauk Point Lighthouse at 12.2 kilometres and the Second House Museum at 20.9 kilometres, with several parks and a golf course within 24 kilometres.
This family-friendly holiday home boasts a private swimming pool, a garden, and a terrace, accommodating up to 19 guests with amenities including air conditioning, WiFi, a fully equipped kitchen, and parking.

Rental villas and holiday homes with jacuzzi in The Hamptons

Fancy a holiday home with hot tub in the Hamptons? Outdoor jacuzzis in private gardens feature among many villas with hot tub.

New Construction Greenport Pool House - 3 Blocks From Town - The Hamptons, NY
10 4 reviews

New Construction Greenport Pool House - 3 Blocks From Town

house, Greenport
Villa In The Hamptons. - The Hamptons, NY
10 14 reviews

Villa In The Hamptons.

house, Hampton Bays
West Hamptons 5br 5baths Heated Pool - The Hamptons, NY
No reviews

West Hamptons 5br 5baths Heated Pool

house, Westhampton
Villa Roman - The Hamptons, NY
9.8 171 reviews

Villa Roman

house, East Quogue
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