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.

Southampton Pool Home Near Village - The Hamptons, NY
No reviews

Southampton Pool Home Near Village

house, North Sea
This Southampton villa is situated on a quiet street, 5.8 kilometres from Shinnecock Hills Golf Club and minutes from Southampton Village.
Boasting a private half-acre with a heated pool, hot tub, and outdoor dining, this holiday home offers four bedrooms accommodating up to eight guests, complete with fast WiFi and ample parking for four cars.
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
Holiday rental. This accommodation is located in East Hampton.
Facilities and services include a terrace, a fridge and a kitchen.
Serene + Private ~ 8 Mins To Main Street + Beaches - The Hamptons, NY
9.8 138 reviews

Serene + Private ~ 8 Mins To Main Street + Beaches

house, Springs
Located in Springs, East Hampton, this apartment is just 1 block from the waterfront and a short 3-minute drive to Springs Tavern + Grill, offering a peaceful retreat close to cultural attractions like the Jackson Pollock House art museum, a mere 5-minute drive away.
This 3-bedroom, 2-bathroom villa rental accommodates up to 6 guests and boasts a private garden with a large swimming pool, BBQ, and firepit, alongside a fully stocked chef's kitchen and an 80-inch streaming TV, making it a superb holiday home.
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
Centrally located in Greenport Village, this luxury villa is a short walk to shops, restaurants, bars, and the beach, offering convenient access to the Greenport Carousel and Camera Obscura.
This spacious holiday home, featuring 4 bedrooms and sleeping 16 guests, boasts a private swimming pool, a hot tub, and an open-concept living area, perfect for groups exploring the Greenport Harbor Brewing Company and Kontokosta Winery.

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.

Premier Waterfront Cottage 3 - The Hamptons, NY
No reviews

Premier Waterfront Cottage 3

house, Aquebogue
Holiday house. Your accommodation will be located in Aquebogue.
Services and facilities: a fridge, air conditioning and an iron. Take advantage of the Free Parking with this accommodation in Aquebogue!
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.
Stunning Westhampton Beach Home W/ Private Pool - The Hamptons, NY
No reviews

Stunning Westhampton Beach Home W/ Private Pool

house, Westhampton Beach
Just an 18-minute walk from Rogers Beach, this Westhampton Beach villa offers a prime location, situated 19 kilometres from Agawam Park and 13 kilometres from Splish Splash.
This spacious holiday home boasts 5 bedrooms, 3 bathrooms, and a generous floor area of 243 square metres, featuring a private outdoor swimming pool, fully equipped kitchen with a dishwasher, and complimentary WiFi for up to 21 guests.
139 M² House ∙ 2 Bedrooms ∙ 5 Guests - The Hamptons, NY
No reviews

139 M² House ∙ 2 Bedrooms ∙ 5 Guests

house, Peconic
Offering spectacular waterfront bluff views across the Long Island Sound, this secluded mid-century contemporary villa rental is set within a private 3-acre property in Peconic, surrounded by local wineries and farms.
This welcoming holiday home accommodates up to 5 guests across 2 bedrooms and features a modern kitchen, air conditioning, a fireplace, and a large deck, with beach rights providing potential for future stair access to the waterfront for an ideal beach house experience.

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.

Hamptons Bay Home On Shinnecock Bay W/ Yard! - The Hamptons, NY
No reviews

Hamptons Bay Home On Shinnecock Bay W/ Yard!

cottage, Hampton Bays
Located in Hampton Bays, this cottage offers convenient access to Regal UA Hampton Bays and Good Ground Park, both less than 1.6 kilometres away, with The Hamptons Beaches and Meschutt Beach within 4.8 kilometres, and Hampton Bays Station just an 11-minute walk away.
This welcoming holiday home provides complimentary WiFi in public areas, free self-parking, and a well-equipped kitchen, making it an ideal villa rental for exploring the local area and enjoying nearby coastal attractions.
Southampton Village 3br Retreat, Stroll To Town - The Hamptons, NY
9.9 25 reviews

Southampton Village 3br Retreat, Stroll To Town

house, Southampton
Located in Southampton Village, this holiday home is a short 300 meters from boutique shops, dining establishments, and Southampton's pristine beaches.
This welcoming 3-bedroom villa offers a well-equipped kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, and a garden, accommodating up to 4 guests with excellent ratings for location, cleanliness, and user experience.
Le Petit Cottage Southold Ny - The Hamptons, NY
9.8 84 reviews

Le Petit Cottage Southold Ny

house, Southold
Just 300 meters from the shores of Little Peconic Bay, this two-bedroom villa rental in Southold offers a prime location for exploring the North Fork, with South Harbor Park Beach, local farms, and the Greenport/Shelter Island Ferry all a short drive away.
This family-friendly holiday home boasts a newly renovated interior with an open-plan living space and a dedicated work-from-home area, while the exterior features a spacious garden and deck perfect for outdoor dining and relaxation, accommodating up to four guests with air conditioning and parking included.
Hampton Bays Retreat: Walk To Squires Beach! - The Hamptons, NY
8.0 1 review

Hampton Bays Retreat: Walk To Squires Beach!

house, Hampton Bays
Just 300 meters from Squires Beach, this Hampton Bays holiday home offers convenient seaside access, situated 31 miles from Montauk Point Lighthouse and 11 miles from Agawam Park.
This welcoming villa rental provides a 134 square meter living space with two bedrooms, accommodating up to 11 guests, complete with a fully equipped kitchen featuring a dishwasher and fridge, air conditioning, and complimentary WiFi.

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.

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.
Southampton Beach & Town Cottage - The Hamptons, NY
10 3 reviews

Southampton Beach & Town Cottage

cottage, Southampton
Just 300 meters from Southampton’s desirable village dining and shops, this family-friendly cottage offers prime access to the beach and the prestigious Gin Lane.
This welcoming villa rental boasts a deep granite swimming pool with heating, a jacuzzi, a patio, an outdoor shower, and a well-equipped kitchen, providing excellent amenities for up to 6 guests seeking a luxurious holiday home experience.
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.
Walk To Love Lane! Immaculately Renovated Private Cottage. - The Hamptons, NY
10 21 reviews

Walk To Love Lane! Immaculately Renovated Private Cottage.

cottage, Mattituck
This welcoming cottage in Mattituck offers a tranquil getaway, just a short walk to popular spots like Strawberry Fields and Windamere restaurant, and a 5-minute drive to Macari Vineyards and Harbes Farm.
This villa rental provides ample entertainment with its expansive garage featuring outdoor furniture, a flat-screen TV, ping pong, foosball, and cornhole, alongside a Solo Stove and Weber BBQ in the garden for al fresco dining, accommodating up to four guests with one bedroom and one bathroom.

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.

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

Villa Flasses - Luxury With Pool

house, Tuckahoe
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 ∙ 4 Bedrooms ∙ 10 Guests - The Hamptons, NY
No reviews

House ∙ 4 Bedrooms ∙ 10 Guests

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

West Hamptons 5br 5baths Heated Pool

house, Westhampton
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