East-End Extravagance: 5 HomeAway & Vrbo Rentals In The Hamptons

East-End Extravagance: 5 HomeAway & Vrbo Rentals In The Hamptons
Contributing Writer
| 5 min read

You’ve already seen this place on screen, be it in Royal Pains, Revenge, Gossip Girl, or other forms of popular media. Chances are, if you’re acquainted with Hollywood’s hottest scenes, you’ll have heard of it – the Hamptons.

Located on the ‘East End’ of New York state’s Long Island, the Hamptons has long been a popular destination for the rich and famous. Defined by the glitz, glamour, and extravagance of high society; this area screams luxury, from the palatial manors of its residents to its range of rich, lavish experiences. It is thus no wonder that some towns of the Hamptons are among the most expensive ZIP codes in the USA.

If you’ve got (lots of) money to spend and want a unique accommodation in the Hamptons, why not opt for a villa? Here are 5 gorgeous HomeAway and Vrbo vacation rentals in the Hamptons, all unique and enchanting for a magnificent getaway:

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on July 16, 2022.

1. Blue beach beauty: beach villa along Westhampton Beach (from USD 3000)

Of all the seasons, the Hamptons is most hectic in the summer. Its long, blond beaches draw many visitors, all seeking a retreat from the heat. During this season, many wealthy people escape to beach-side properties for a peaceful holiday; now you can too, with this beautiful beachfront villa! Built in a contemporary architectural style, this white-and-glass house appears sleek, modern, and capacious. Beachfront is no exaggeration – the sand is just steps from the sliding doors! True to its contemporary nature, the house’s interiors bear an unconventional layout – the bedroom is on the first floor! But who can complain when you’re waking up in paradise with such a view in front of you? More maverick living comes on the floor upstairs, where an open-concept living space of wood, white, and blue awaits. A Santorinian-like scheme of deep blue and white colors the living area, a matching view just beyond its glass walls. Lounge on the U-shaped sofa, a furnishing large enough for you to get together with everyone. Cook, chat, or make some coffee in this ebony-furnished kitchen, or watch culinary magic being made from the comfort of these barstools. Tired of the indoors, but don’t want the sand in your shoes? Step out to the balcony for its panoramic beach view. Alternatively, admire the beauty of the Atlantic from the comfort of the lounge. With a fireplace by the stairs, this villa is suitable as a home for all seasons.

Stayed at this property?

15.55 km (9.7 mi) from Splish Splash Water Park
10 reviews  
Apartment 6 Guests 2 Bedrooms 4 Bathrooms

Accommodates: 6
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
lauren was extremely attentive and efficient in accommodating any of our concerns or requests
rating details:the property manager was very helpful
rating details:the property manager was very helpful
reviewer comments:absolutely wonderful everything was as shown online and the staff and lauren were a delight
great location and views
i was very happy with the location
i was very happy with the location
Read more reviews

2. State of the art: contemporary villa in Water Mill (from 897 USD)

The affluent are often associated with an appreciation for the arts. Be it in avant-garde architecture or experimental works, their taste in the subject is one both cryptic and refined. Live this enigmatic perspective through this villa, another contemporary masterpiece. Situated in the heart of four acres (1.6 hectares) of woodland, expect a serene, secluded stay in this residence. Spend your days invoking your inner muse, or bask in the sunshine with the cool of the pool. Sick of swimming? Get some exercise on this tennis court! Defined by regal woodland minimalism, the villa’s interiors comprise parquet flooring and oak paneling, complemented by sparing pieces of wooden furniture. All-white interiors are all the rage in the Hamptons, and this living room is no exception. Lounge in an artistic atmosphere, enhanced by a fireplace and artwork. Time for some TLC! Marble floors and an open-concept bathtub give you a grand atmosphere to relax in. When it’s time for bed, retreat to this breezy bedroom. You can watch your little ones play on the floor as you curl up with your loved one in the king-sized bed.

Filled with Art

Area: Water Mill, Southampton

Price: from 897 USD

Number of Guests: 12

Stayed at this property?

3. Flower power: designer dwelling in Northwest Harbor (1,990 USD)

Are you a fan of flora, fauna, or anything natural? This residence is the place for you! Live in the midst of a modern-day Eden with this East Hampton villa, sitting right next to a nature reserve. As you pull up to the front of this house, paradise greets you. Vibrant flowers and blossoming trees line the path to your home, heralding a holiday of lush glamour. Modern and medieval meet in the house’s foyer, providing the atmosphere of a palace within the woods. This regal air extends further into the home. Take a look at this living room – above the zebra-skin rug, a crystal chandelier hangs, bathing the space in a muted glow. Live like a prince or princess, and sleep like a king or queen. Retreat to this bedroom of historic royalty, with a king-sized canopy bed to bid you goodnight. Out back, a stone-tiled patio overlooks the swimming pool. Take a post-swim nap, or tan on the deck chairs! Perhaps the most spectacular part of this residence, the dining area features a long row of seats beneath towering vases of flowers. Imagine dining beneath the blossoms of spring as you indulge in the day’s culinary delights.

Designer Home Surrounded By Nature

Area: Northwest Harbor, East Hampton

Price: from 1,990 USD

Number of Guests: 16

Stayed at this property?

4. Wooden wonderland: handcrafted cabin outside North Sea (from 714 USD)

Besides its sugary beaches and opulent villas, the Hamptons is known for its preserved natural beauty. Experience this beauty among a biodiversity of trees in this handcrafted cabin, tucked away in a secluded side of Southampton. Traverse a stepping-stone trail to the home’s front, a tidy bluestone patio perfect for a barbecue party. The cabin may look quite shabby on the outside … … But the inside tells an entirely different story. Ascend the stairs to the upper floor, where you’ll find an open-concept living space decked out in wood. Allow the warm shades of this home to draw you into an embrace as you lounge in this living room. Regardless of the season, enjoy warmth, comfort, and congeniality before this very fireplace! A contrast from the outside, this bedroom awaits in woodland shades. Drift off to dreamland in this calming atmosphere, made more comfortable with a king-sized bed and velvet armchair. The bathroom comes in a similar scheme, with jade shades and a bamboo plant providing an air of calm. Unwind after an exciting day in the cool waters of the shower, or freshen up in glamour with the jade-like sinks.

Handcrafted Hamptons Home

Area: North Sea, Southampton

Price: from 714 USD

Number of Guests: 10

Stayed at this property?

5. Festive farmhouse: barn-inspired villa in Southampton (from 712 USD)

Before its boom as a holiday destination in the 1890s, the Hamptons was a community of villages and hamlets specialized in potato farming. Return to these roots with this farmhouse mansion, tucked away in a picturesque corner of Southampton. Rustic royalty awaits as you pull up to this manor. Imagine this place in winter – a snow-coated wonderland of fairy lights and festivity; all yours at a fraction of the cost of summer rental! The living room exudes a wintry ambiance, employing copious amounts of white to sparing blues and browns. Mingle with the family, cozy up by the fireplace, or set up a Christmas tree in this commodious space. The master bedroom gives off an entirely different vibe. From piercing shades of red to champagne-colored walls, the room radiates a rather Asian style of chic. Entertain guests in rattan chairs by the fireplace, or relax as you watch television from the king-sized bed. Another room of Eastern ambiance, the mansion’s second bedroom is a bamboo-green world of serenity. Rest comfortably upon the plush bed and wake up to tranquility every morning. It’s back to basics in this bathroom, a roomy space of sparse furnishings. Luxury is provided though as you lounge in the open-concept bathtub, a crystal chandelier hanging overhead.

The Infamous Hamptons In the Winter!

Area: Southampton Village, Southampton

Price: from 712 USD

Number of Guests: 10

Stayed at this property?

Live the high life in the Hamptons

The Hamptons is a land of no less than the best. You can experience the best luxury with these stunning HomeAway and VRBO residences. Bask in the glitz and glamour of the atmosphere as the unique charms of these homes present a holiday experience like no other.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Brenda is a vibrant individual passionate about (way too) many things. An explorer, artist and optimist at heart, she is in love with the world and the beauty it has to offer. Her travels thus far...Read more

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