Luxury rentals in Southampton

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Top-rated luxury vacation rentals in Southampton

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Luxe

The exterior of the beach cottage reveals a spacious layout with a two-story design. A manicured lawn surrounds the area, complemented by a sleek swimming pool in the foreground. A chess set is positioned on the grass, while mature trees and flowering shrubs add natural beauty.

Villa in East Hampton

Skimhampton Road

The sounds of the city are miles away at this tranquil beach cottage. Exposed brick, creamy white walls, and glossy hardwood flooring detail a cozy atmosphere. Skylights punctuate the soaring ceilings and rows of elongated windows bathe the living space in a blanket of natural light. Drive 2 minutes to Amagansett where luxury boutiques, fine dining, and fitness classes satisfy every excursion. Plump couches invite you to sit down for a morning coffee while embracing the silence of the country. Fragrant rose bushes and dense shrubbery line the perimeter, giving you a sense of total privacy. Feel the fresh grass tickle your feet as you walk across the manicured lawn. A gunite saltwater pool is a refreshing option on summer scorchers, followed by the hot tub which will soak away your stress. When the sun sets, why not gather around the roaring patio fireplace? East Hampton Main Beach is a short, scenic route away where you’ll find a snack bar, gently rolling waves, and endlessly stretching shoreline. Visit a museum or winery in Sag Harbor, settle in at a small town café in Bridgehampton, or tee off at Sag Harbor Golf Course. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Master: King size bed, Ensuite bathroom with stand-alone rain shower & bathtub, Dual vanity, Walk-in closet, Fireplace, Television, Direct access to patio • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower, Dual vanity, Walk-in closet, Lounge area • Bedroom 3: King size bed, Ensuite bathroom with stand-alone shower, Television • Bedroom 4: King size bed, Shared access to hallway bathroom with bedroom 5, Shower/bathtub combo, Dual vanity, Television • Bedroom 5: 2 Twin size beds, Shared access to hallway bathroom with bedroom 4, Shower/bathtub combo, Dual vanity, Television • Bedroom 6: 2 Twin size beds, Access to hallway bathroom with stand-alone shower, Dual vanity, Walk-in closet Additional bedding: • Bunk room: 2 Twin over double size bunk beds, Access to hallway bathroom with stand-alone shower, Dual vanity OUTDOOR FEATURES • Swimming pool - seasonal availability, heating included • Hot tub - seasonal availability, heating included • Chess set • Security cameras - outward facing • More under “What this place offers” below STAFF & SERVICES Extra cost (advance notice may be required): • Laundry service • More under “Add-on services” below LOCATION Points of Interest • 2 minute drive to Amagansett • 3 minute minute drive to East Hampton • 7.4 miles to Sag Harbor Golf Course • 8.2 miles to Bridgehampton • 8.5 miles to Sag Harbor Beach Access • 7 minute drive to East Hampton Main Beach • 8.3 miles to Havens Beach • 11 miles to Foster Memorial Town Beach Airport • 5.7 miles to East Hampton Airport (HTO) • 30 miles to Francis S. Gabreski Airport (FOK) • 94 miles to John F. Kennedy International Airport (JFK)

Luxe

A modern two-story home is set against a backdrop of trees at dusk, with warm lights glowing from the windows. The inviting saltwater pool reflects the home’s exterior, basking in hues of blue, while outdoor seating surrounds the pool area.

Villa in East Hampton

4.95 out of 5 average rating, 21 reviews

Chic Modern Oasis

Lush, green, and private, this modern oasis connects you to nature. Impeccably decorated, the serene estate recently underwent a renovation that left the interior with a sleek, natural palette, textured accent rugs, artful fixtures, and soft wooden décor. Located in the heart of East Hampton, you’re just a short 5-minute drive away from town where you’ll find beaches, lakes, and verdant vineyards. A multitude of windows set the interior ablaze during the brightest times of day, exuding a light and airy atmosphere. Flowing common spaces connect to the rest of the home; there are plenty of seating areas to gather around with the whole crew or to intimately converse in a small group. Sumptuous, sugar-white sofas invite you to take a seat in front of the roaring living room fireplace—perhaps with a cup of hot cocoa in hand? From the mahogany deck, stroll down the landscaped backyard to reach the heated saltwater pool. The 2-acre property features its own trails that wind their way through a dense forest. Endless beach shorelines, swaying ocean tides, and a lush nature reserve are less than 2 miles north; a tranquil walk or jog from the house. Rent a bike in nearby Amagansett and cycle around to various museums, parks, and squares. A trip to Sag Harbor will complete your stay with a selection of seaside restaurants serving the freshest fare and local wines. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM First floor • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower, Walk-in closet, Television • Bedroom 2: Queen size bed, Ensuite bathroom with shower/bathtub combo, Television • Bedroom 3: 3 Twin size beds, Ensuite bathroom with stand-alone shower Ground floor • Bedroom 4: Queen size bed, Access to hallway bathroom with stand-alone shower, Television, Private balcony • Bedroom 5: Double size bed, Twin size bed, Access to hallway bathroom with stand-alone shower, Television Additional Bedding • Spare Room: Sofa bed OUTDOOR FEATURES • Terrace • More under “What this place offers” below STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Luxe

A large outdoor area includes a heated pool surrounded by loungers and umbrellas. A spacious lawn is complemented by a deck and lush greenery, enhancing the serene setting. The house features a classic design with white siding and multiple windows for natural light.

Home in Bridgehampton

5 out of 5 average rating, 3 reviews

Ideal September Home w/ Heated Pool. Sag &Bridge.

Newly renovated 4bed 3.5 bath that is equidistant from Bridgehampton and Sag Harbor. This beautifully designed house has a 20x40 heated pool as well as a large outdoor area, with outdoor shower, loungers and dining space next to a gas barbecue. Inside, the lower level includes of a beautiful large open space perfect for indoor/outdoor living where the family, dining room and kitchen all combine with hi-tech appliances such as a 65inch smart TV, SONOS surround system (incl outdoor) and NEST AC

Luxe

An expansive backyard features a large rectangular pool surrounded by a manicured lawn. Sun loungers are aligned poolside, and a covered pergola with seating is visible. The elegant home is set against a backdrop of lush trees and a clear blue sky.

Home in East Hampton

5 out of 5 average rating, 13 reviews

5 Bedrms Fam Friendly Heated Pool Firepit Gym

*NO PETS* Luxury Hamptons home: 5 Bedrooms, 4.5 Baths of complete privacy & tranquility in East Hampton. We gut renovated & thoughtfully curated everything for your family to enjoy. Fully outfitted kitchen, multiple fam areas, luxury beds & linens. Heated pool (see rules), outdoor kitchen & fire pit area. Lush gardens. Blackout shades in all bedrooms. Crib, high chair, gates & pool fence avail. Outlets/wifi poolside. Central AC. Outdoor shower. No pets, no smoking, no parties. Reg#24-493

Luxe

A spacious backyard features a shimmering pool surrounded by lounge chairs. A fire pit sits nearby, while a shaded pergola provides a seating area. Lush greenery and trees create a serene atmosphere, offering a private setting for relaxation.

Villa in Amagansett

5 out of 5 average rating, 3 reviews

Amagansett Beach Home

Totally renovated 6 bedroom, 7.5 bathroom house with newly built outdoor amenities including a 46 ft long pool, an in-pool hot tub / spa, a Finnish sauna, a huge outdoor kitchen and bar area that includes an ice maker, dishwasher, sink with hot water, Green Egg grill, refrigerator and a 48" propane grill. Inside the main home, you will find indoor / outdoor spaces under a covered 500 sq porch, a chef's kitchen, a wet bar with an ice maker, 3 dedicated workspaces, a gym, and a movie theater.

Luxe

A contemporary A-frame structure is set amidst lush greenery, featuring a spacious deck with outdoor seating under a market umbrella. Large windows reflect the natural surroundings, while a glistening pool is visible in the foreground, adding a touch of relaxation to the inviting landscape.

Home in Hampton Bays

5 out of 5 average rating, 10 reviews

Lux A-frame: Secluded pool retreat & walk to beach

Just awarded Dwell Magazines Bright Ideas Stand Out Project, this home is both stunning and unique. You can experience the magic of summer in the Hamptons, where charming coastal beauty meets carefree beach days. Enjoy walks along the beach, explore quaint shops, and experience charming local dining. Our unique home offers a perfect retreat for families or large groups, complete with a fireplace, 30f ceilings, ample seating and beds, kids games & toys, beach & tennis gear and stunning views.

Luxe

An outdoor area is shown with a sleek swimming pool in the foreground, surrounded by a manicured lawn. Several lounge chairs are arranged near a central fire pit, with large glass doors revealing the modern interior. Lush greenery borders the space, adding a natural touch.

Home in East Hampton

Designer's Home in Amagansett

Not your average rental property, this stunning Mid-Century Modern home was designed by Athena Calderone and featured in Architectural Digest (Feb 2020). Renovated by Bates Masi, the property has been fully updated with modern appliances, luxurious finishes, curated furniture, art, and decor. The sun-drenched home features 4 beds, 3.5 baths. Designed for entertaining, the home centers around an oversized kitchen. Set on 1.5 private acres the property includes heated pool, hot tub, & home gym.

Luxe

A tennis court is surrounded by lush trees, providing a natural setting for outdoor activity. The court features a smooth surface, with clearly marked lines and a basketball hoop visible in the background. Sunlight filters through the leaves, enhancing the serene ambiance.

Home in Sagaponack

5 out of 5 average rating, 3 reviews

Designer's Hamptons Stunner

A stunning retreat in Sagaponack, situated on 2.8 acres. Designed by renowned architect Robert A.M. Stern, and owned by a celebrated interior designer, the home exudes comfort & style, with access to East Hampton, Sag Harbor, and gorgeous ocean beaches. Hosting capabilities with connecting dining room and living room with fireplace, and expansive screened-in porch. The home features immaculately designed interiors, and outside are sprawling lawns, a large heated pool & spa, and tennis court.

Luxe

A modern living area is displayed with light-colored furniture, including two patterned armchairs, a round leather ottoman, and a cozy seating arrangement. A fireplace is framed by built-in shelves showcasing decorative items and a large framed photograph hangs above, complementing the bright ambiance.

Home in East Quogue

5 out of 5 average rating, 13 reviews

Charming, Beautiful Hamptons Gem

The East Quogue Hideaway is the ultimate charming getaway, beautifully secluded, but only 90 mins from NYC and minutes from the East End’s best beaches and towns. Recently renovated, the house is surrounded by award-winning gardens, and features four outdoor areas including a large deck with lounge & dining, three large en-suite bedrooms, luxury mattresses, flatscreen TVs, and a well-stocked chef’s kitchen. 10 mins to Westhampton, 5 min to Quogue village, 15 mins to Southampton & North Fork.

Luxe

An inviting outdoor seating area features comfortable lounge chairs and a coffee table, surrounded by lush greenery. The scenic view reveals a calm waterfront, where trees line the shore and gently sway in the breeze.

Home in Sag Harbor

Sag Harbor Getaway

Escape to this newly renovated Sag Harbor waterfront retreat, just 5 minutes from town. This 6-bedroom, 4.5-bath gem offers stunning views, a private beach, and a luxurious spa with a hot tub, sauna, and steam room. Enjoy paddleboarding or kayaking from your private dock and beach, or work out with the on-site fitness equipment. Ideal for families or groups seeking relaxation and adventure, this home delivers the ultimate Hamptons getaway. Book now to experience waterfront Hamptons living!

Luxe

Home in East Hampton

5 out of 5 average rating, 7 reviews

Modern sanctuary

brand new 7400 residence. 8 bedrooms, 8.5 bath. open floor plan establishes an immediate connection between the living space and the outdoors. Sliding glass doors and a southern orientation taking full advantage of the sun's rays. An expansive mahogany sun deck transitions you outside to the al fresco dining and lounging spaces, featuring a built-in gas grill and overlooking the spacious backyard, complete with a saltwater gunite pool with spa and a grand play-set. No parties No smoking

Luxe

An outdoor area is showcased, featuring a spacious heated pool surrounded by a paved patio. Lounge chairs are arranged along the poolside, while a shaded umbrella provides a relaxing spot. Lush greenery and waterfront views enhance the serene atmosphere.

Home in Hampton Bays

5 out of 5 average rating, 10 reviews

Hamptons • Waterfront Estate •

Set on the waterfront of Tiana Bay, this estate-like Hamptons home offers guests incredible ocean views, and close proximity to the Ponquogue Beach and some of the area’s most beloved wineries. At home, you’ll enjoy a heated pool, hot tub, and a Peleton, as well as kayaks and paddleboards to help explore the coast. In an environment like this, you’ll definitely want to dine alfresco. Copyright © Luxury Retreats. All rights reserved.