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.

Summerlight Estate By Rove Travel - Villa With Pool - The Hamptons, NY
No reviews

Summerlight Estate By Rove Travel - Villa With Pool

house, Montauk
Located a short 19-minute walk from Hither Hills State Park, this spacious Montauk villa is also conveniently situated 5.9 kilometres from Montauk Point Lighthouse, with Second House Museum and Fort Pond Bay Park just 3.5 kilometres away.
This welcoming four-bedroom, five-bathroom holiday home offers a generous 249 square meters of living space for up to nine guests, featuring a private swimming pool, a garden, a terrace, air conditioning, and complimentary WiFi.
Pinkwood Playhouse, Pool, Golfsim, Hottub, Movie, Games, Firepit, Dogs - The Hamptons, NY
No reviews

Pinkwood Playhouse, Pool, Golfsim, Hottub, Movie, Games, Firepit, Dogs

house, Northwest Harbor
Located in East Hampton, this villa is approximately 19 kilometres from Fort Pond Bay Park and Montauk Downs State Park Golf Course, with Montauk Point Lighthouse 19 kilometres away.
This expansive holiday home boasts four bedrooms, three bathrooms, and a guest capacity of 15, offering a games room, mini golf, a movie theatre, and entertainment staff for all ages, alongside a seasonal swimming pool and hot tub.
4 Bed 2 Bath - Salt Water Pool Close & Beaches - The Hamptons, NY
9.5 2 reviews

4 Bed 2 Bath - Salt Water Pool Close & Beaches

house, Water Mill
Located in Southampton, this villa is situated 32 kilometres from Montauk Point Lighthouse and 37 kilometres from Splish Splash.
This welcoming 204 square metre holiday home offers 4 bedrooms, sleeping up to 14 guests, with a private beach area, saltwater swimming pool, and outdoor dining facilities.
Villa Noyaan - Luxury With Pool - The Hamptons, NY
No reviews

Villa Noyaan - Luxury With Pool

house, Southampton
Villa Noyaan offers a luxurious villa experience in Southampton, conveniently located just 1.5 miles from Flying Point Beach, providing easy access for beach enthusiasts.
This spacious holiday home boasts 6 bedrooms, sleeping up to 27 guests, and features a private outdoor swimming pool, sauna, and a well-equipped kitchen with a balcony and barbecue facilities, alongside on-site parking and a fitness centre.

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.

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.
5th Of 6 Premier Waterfront Vacation Rentals On Long Island Ny In Wine Country Of Famed North Fork - The Hamptons, NY
10 3 reviews

5th Of 6 Premier Waterfront Vacation Rentals On Long Island Ny In Wine Country Of Famed North Fork

cottage, Aquebogue
Directly on the Peconic Bay, this Aquebogue cottage offers 365 feet of waterfront frontage on the North Fork of Long Island, providing convenient access to over 40 local wineries and a variety of attractions.
This pet-friendly villa rental, featuring two bedrooms and accommodating up to five guests, boasts complimentary kayaks, paddle boards, and canoes for bay exploration, alongside included beach passes to five local town beaches.
Cozy Cottage Steps From The Beach In The North Fork - The Hamptons, NY
10 1 review

Cozy Cottage Steps From The Beach In The North Fork

cottage, Baiting Hollow
Perched on a bluff overlooking the Long Island Sound, this Baiting Hollow cottage offers direct access to a private beach, located just 300 meters from a water park and a short distance from the Suffolk Theater.
This welcoming villa rental provides accommodation for six guests across three bedrooms, featuring a recently updated chef's kitchen, a deck with outdoor lounge furniture, and high-speed WiFi, making it an ideal holiday home for exploring the North Fork's attractions like Baiting Hallow Golf Club and Roanoke Vineyards.
Sag Harbor Charmer - 2 Bedroom Cottage; Walk To Town - The Hamptons, NY
9.7 153 reviews

Sag Harbor Charmer - 2 Bedroom Cottage; Walk To Town

cottage, Sag Harbor
Located in a historic Sag Harbor neighbourhood, Beech Tree Cottage is a mere 5-minute walk to Sag Harbor's Main Street and waterfront, with Hamptons beaches a short drive away.
This fully-furnished, two-storey cottage offers 139 square meters of living space, accommodating up to 4 guests with 2 bedrooms and 1 bathroom, featuring a fully equipped kitchen, wireless internet, and a private garden with a spa and off-street parking.

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.

Quiet Luxury In The Heart Of The Hamptons - The Hamptons, NY
No reviews

Quiet Luxury In The Heart Of The Hamptons

house, Bridgehampton
Located in Bridgehampton, this exclusive villa rental is situated 26 kilometres from Montauk Point Lighthouse and 34 kilometres from the Second House Museum, offering convenient access to Hamptons attractions.
This expansive holiday home provides accommodation for up to 12 guests across 4 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, air conditioning, a swimming pool, and on-site parking, with nearby attractions including Hither Woods Preserve and Shadmoor State Park.
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 Flasses - Luxury With Pool - The Hamptons, NY
No reviews

Villa Flasses - Luxury With Pool

house, Tuckahoe
Villa Flasses is a luxury villa located in Tuckahoe, offering a private pool, solarium, and open-air bath, situated 29 kilometres from Splish Splash and 39 kilometres from Montauk Point Lighthouse.
This expansive 251 square metre holiday home accommodates up to 15 guests across 5 bedrooms, featuring complimentary WiFi, a fully equipped kitchen, and outdoor dining facilities, with secure free private parking available.
New Construction Modern Luxury Retreat W 6 Beds - The Hamptons, NY
9.0 2 reviews

New Construction Modern Luxury Retreat W 6 Beds

house, North Sea
Located in Southampton, this magnificent villa rental is 35 kilometers from Montauk Point Lighthouse and 37 kilometers from Splish Splash, offering exclusive access to a private beach area.
This spacious 465 square meter holiday home boasts 6 bedrooms, 6 bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, and a terrace with garden views, comfortably accommodating up to 23 guests.

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 Xmart - Luxury With Pool - The Hamptons, NY
No reviews

Villa Xmart - Luxury With Pool

house, Water Mill
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.
Villa Nostro Palazzo - The Hamptons, NY
No reviews

Villa Nostro Palazzo

house, Wainscott
Villa Nostro Palazzo is located in East Hampton, 19 kilometers from Montauk Point Lighthouse and 29 kilometers from the Second House Museum, with Hither Woods Preserve and Fort Pond Bay Park also in close proximity.
This luxurious seven-bedroom, five-bathroom villa rental offers a spacious retreat with an indoor swimming pool, hot tub, sauna, and expansive terrace, perfect for family gatherings or groups seeking exclusive holiday accommodation.
Tennis & Sea Escape - Hydrangeas In The Hamptons - The Hamptons, NY
No reviews

Tennis & Sea Escape - Hydrangeas In The Hamptons

house, Westhampton Beach
Just 300 meters from Westhampton Beach's shores, this exclusive cabana offers a secluded retreat near the town centre, providing convenient access to both relaxation and local attractions. This villa rental boasts a private har-tru tennis court, a spacious garden with lounge seating and a hammock, and EV charging capability, perfect for a family-friendly holiday home accommodating up to two guests.
Charming Beach Cottage, Steps To Beach, Enjoy Scenic Vineyards & Farm Stands - The Hamptons, NY
10 2 reviews

Charming Beach Cottage, Steps To Beach, Enjoy Scenic Vineyards & Farm Stands

cottage, Jamesport
Directly adjacent to the white sandy beach of the South Jamesport community, this cottage offers a prime location within the Historic South Jamesport beach community, just steps from the coastline and a local seafood restaurant.
This welcoming villa rental, perfect for families, accommodates up to 6 guests with 3 bedrooms and 1 bathroom, featuring a well-equipped kitchen, air conditioning, and a garden with a propane barbeque, providing convenient access to Sherwood House Vineyards and Harbes Family Farm.

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.

Waterfront Hot Tub Retreat W Kayaks | Kayak Point - The Hamptons, NY
No reviews

Waterfront Hot Tub Retreat W Kayaks | Kayak Point

house, Southold
Pool|golf Sim|hottub|movie|games|firepit|golf Open - The Hamptons, NY
9.9 95 reviews

Pool|golf Sim|hottub|movie|games|firepit|golf Open

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

West Hamptons 5br 5baths Heated Pool

house, Westhampton
House By The Bay: Heated Pool, Hot Tub, Gym, Sauna - The Hamptons, NY
10 4 reviews

House By The Bay: Heated Pool, Hot Tub, Gym, Sauna

house, Hampton Bays
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