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.

Villa Lalam - The Hamptons, NY
No reviews

Villa Lalam

house, Shinnecock Hills
Villa Lalam, located in Southampton's Shinnecock Hills, is ideally situated for exploring local attractions, being 24 kilometres from Montauk Point Lighthouse and 29 kilometres from the Second House Museum.
This spacious 232 square meter villa rental offers five bedrooms, a fully equipped kitchen, air conditioning, and a delightful garden with a swimming pool and terrace, alongside an on-site bar and complimentary WiFi.
Serene Beach Oasis W/ Hottub & Salt Water Htd Pool - The Hamptons, NY
9.8 24 reviews

Serene Beach Oasis W/ Hottub & Salt Water Htd Pool

house, Hampton Bays
Just 300 meters from the beach, this Hampton Bays villa rental offers a serene oasis with a saltwater pool and hot tub, located a mere 2 minutes from the local town and 12 kilometers from South Hampton Village.
This family-friendly holiday home boasts 3 bedrooms and 2 bathrooms, accommodating up to 6 guests with a fully equipped kitchen, air conditioning, and generous outdoor living space featuring an outdoor kitchen and fish pond.
Modern Comfy Retreat Patio Outdoor Salt Hot Tub - The Hamptons, NY
10 1 review

Modern Comfy Retreat Patio Outdoor Salt Hot Tub

house, Northwest Harbor
Located in East Hampton, this holiday home offers proximity to Montauk Point Lighthouse, situated 8.4 kilometres away, and is within 14 to 16 kilometres of various state parks and museums.
This 2-bedroom villa rental boasts a floor area of 167 square meters, accommodates up to 11 guests, and features a well-equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, and a garden for a comfortable stay.
Hampton Private Retreat - Last Minute Offer June 23- - The Hamptons, NY
10 24 reviews

Hampton Private Retreat - Last Minute Offer June 23-

house, North Sea
North of the highway, this exclusive Southampton villa boasts a unique waterfront location offering exceptional privacy, just a 5-minute drive from the North Sea beaches and 10 minutes from Southampton Village.
This spacious 530 square meter holiday home accommodates up to 10 guests with 5 bedrooms and 5 bathrooms, featuring a full basement with a gym and media room, alongside a landscaped garden with a pool and brand-new furniture.

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.

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.
Bayfront East Quogue Retreat W/ Private Boat Dock - The Hamptons, NY
No reviews

Bayfront East Quogue Retreat W/ Private Boat Dock

cottage, East Quogue
Nestled in East Quogue, this cottage offers a private patio and is conveniently located 4.3 kilometres from Quogue Community Hall and within 9.7 kilometres of Cupsoque Beach and Rogers Beach, placing you near The Hamptons Beaches and Regal UA Hampton Bays.
This welcoming holiday home boasts a fully equipped kitchen with microwave, air conditioning, and complimentary WiFi in public areas, alongside on-site barbecue grills and free self-parking, ensuring a comfortable stay for your villa rental experience.
Premier Waterfront Cottage 3 - The Hamptons, NY
9.7 97 reviews

Premier Waterfront Cottage 3

house, Aquebogue
Premier waterfront cottage in Riverhead offering direct water access, this villa rental is conveniently situated 12.2 kilometres from Splish Splash water park.
This welcoming holiday home boasts a fully equipped kitchen, air conditioning, a garden with an outdoor dining area, and complimentary private parking, with free Wi-Fi available throughout the property.
Bayfront East Quogue Retreat W/ Private Boat Dock - The Hamptons, NY
No reviews

Bayfront East Quogue Retreat W/ Private Boat Dock

house, East Quogue
Located in East Quogue, this prime bayfront villa offers a private boat dock and convenient access to Splish Splash amusement park, just 19 kilometres away.
This welcoming holiday home features 2 bedrooms, air conditioning, and a fully equipped kitchen with an oven and coffee machine, plus an outdoor dining area and complimentary WiFi throughout.

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.

Chic Modern Retreat In The Heart Of Eh! Pool Open! - The Hamptons, NY
No reviews

Chic Modern Retreat In The Heart Of Eh! Pool Open!

house, East Hampton
House rental listing. Your accommodation will be based in East Hampton.
Services and facilities: a jacuzzi, an iron and air conditioning. This house is ideal for families.
Villa Revello - Luxury With Pool - The Hamptons, NY
No reviews

Villa Revello - Luxury With Pool

house, Shinnecock Hills
Villa Revello, a luxurious 5-bedroom villa, is situated in Southampton, 30 kilometres from Splish Splash and 38 kilometres from Montauk Point Lighthouse.
This expansive holiday home, covering 307 square meters, accommodates up to 19 guests and features a private swimming pool, jacuzzi, terrace, garden, on-site bar, and room service for an exclusive stay.
Charming Waterfront English Cottage With Private Bay Beach In A Nature Preserve - The Hamptons, NY
9.8 41 reviews

Charming Waterfront English Cottage With Private Bay Beach In A Nature Preserve

cottage, Flanders
Located in Riverhead, this cottage is just a 15-minute drive from Southampton and Westhampton villages, offering convenient access to the renowned Cooper's Ocean Beach and a private bay beach with gentle swimming, making it an ideal beach house destination.
This 111 square meter villa rental accommodates up to six guests and features air conditioning, a kitchen with a fridge, and a terrace, with access to a 3-person ocean kayak and a heated outdoor shower for exploring the surrounding nature preserve.
Steps To Beach + Sunset Views! East Marion Home - The Hamptons, NY
No reviews

Steps To Beach + Sunset Views! East Marion Home

cottage, East Marion
Conveniently located in East Marion, this cottage is within 5 kilometres of Island's End Golf and Country Club, Truman's Beach, and Kontokosta Winery, with Safe Harbor Stirling also nearby.
This villa rental offers a full kitchen with oven, stovetop, microwave, and dishwasher, a patio, a TV, two bathrooms, and barbecue grills, with internet and air conditioning provided for your comfort.

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.

Beautiful Airy Barn In Springs - The Hamptons, NY
9.8 221 reviews

Beautiful Airy Barn In Springs

house, Springs
Located in Springs, this welcoming guest cottage/barn is just a 5-minute bike ride from the sea and a short drive to ocean beaches, offering convenient access to Acabonac Bay, Amagansett, Napeague, East Hampton, 3 Mile Harbour, Sag Harbor, and Montauk.
This exclusive villa rental boasts a private gunnite pool, an outdoor shower, and a deck with views, all set on 1.5 acres and accommodating up to 3 guests with amenities including a fridge and microwave, making it an ideal holiday home.
Close To All! Peaceful Heated Pool! *Month - The Hamptons, NY
9.8 18 reviews

Close To All! Peaceful Heated Pool! *Month

cabin, Wainscott
Located on the village fringe of Wainscott, this welcoming log home offers a peaceful cul-de-sac setting just 400 meters from the ocean beaches and close to East Hampton Village amenities.
This family-friendly villa rental boasts a heated 20x40 swimming pool, a garden with teak furniture and hammock, high-speed wireless internet, and accommodates up to six guests across its 4 bedrooms and 2 bathrooms.
Us Golf Open & Ocean View Retreat, Walk To Event - The Hamptons, NY
9.7 6 reviews

Us Golf Open & Ocean View Retreat, Walk To Event

house, Shinnecock Hills
South of the highway in Shinnecock Hills, this exclusive villa offers breathtaking views of Shinnecock Bay and the Atlantic Ocean, located just a short walk from the 2026 US Open at Shinnecock Hills Golf Club and minutes from South Hampton Village.
Boasting 4 bedrooms and 3.5 bathrooms for up to 6 guests, this secluded holiday home features a private garden, swimming pool, and air conditioning, providing a tranquil coastal escape close to world-class beaches and fine dining.
Private, Charming, Lovely Farmhouse In Wainscott, East Hampton - The Hamptons, NY
10 117 reviews

Private, Charming, Lovely Farmhouse In Wainscott, East Hampton

farm, Wainscott
Located in the exclusive Wainscott hamlet of East Hampton, this luxury villa sits directly on the shores of Georgica Pond, just a few kilometres from white sand beaches.
This expansive 186 square meter holiday home accommodates up to six guests across three bedrooms and three bathrooms, boasting a private heated swimming pool, a mahogany deck, and high-speed wireless internet.

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.

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

West Hamptons 5br 5baths Heated Pool

house, Westhampton
Private Westhampton Escape 5br, Pool, Hot Tub, Near Beach - The Hamptons, NY
9.4 34 reviews

Private Westhampton Escape 5br, Pool, Hot Tub, Near Beach

house, Westhampton
Bridies Edge - Southampton W/ Gunite Pool & Spa - The Hamptons, NY
9.6 34 reviews

Bridies Edge - Southampton W/ Gunite Pool & Spa

house, North Sea
Villa Burak - Luxury With Pool - The Hamptons, NY
No reviews

Villa Burak - Luxury With Pool

house, Bridgehampton
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