
Luxury rentals in Long Island
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Top-rated luxury holiday rentals in Long Island
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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)

Lux 5BR A-frame: Heated Pool, 10m to 2026 US Open
Escape to our Dwell Magazine-featured A-frame in the Hamptons! This stunning unique home is perfect for families or groups of up to 12. Enjoy a private pool, chef's kitchen, and designer details throughout. With 5 bedrooms, soaring ceilings, cozy fireplace, a large deck, private heated pool and lush yard, it's the ultimate luxury retreat for carefree beach days and creating lasting memories. Just minutes from the beach and local attractions, this properly is fully equipped for families & groups.

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

5 Bedrms Fam Friendly Heated Pool Firepit Gym
*NO PETS* Xmas Tree up for winter! 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. Central AC. Outdoor shower. No pets, no smoking, no parties Reg#24-493
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.

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.

Charming, Beautiful Hamptons/North Fork 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.

Ocean View 5 BR w. Pool on Point O' Woods Border
Just one house back from the beach, this brand new construction home is spectacular. With a 30’ pool, panoramic ocean views, and multiple entertaining areas, this home does not disappoint. All 5 bedrooms have private en-suite bathrooms and sliding doors leading directly to outdoor spaces. The home also features a large den, office area, gym, and 2 outdoor showers. Enjoy the pool deck, covered outdoor lounge, dining deck with outdoor kitchen and roof deck with 360 views and massive wetbar.

Montauk modern 7-bedroom Heated Pool & hot tub
This highly appointed new construction home is ideally located just moments to Gurneys, Ocean Beaches and Montauk Village. 6 bedrooms, 5 full baths, grand vaulted living space, wood burning fireplace, alfresco chef's kitchen, ocean view roof terrace, heated gunite pool with integrated hot tub open year around, expansive exterior patio, outdoor kitchen and shower, and detached garage, all on a private manicured parcel. A true resort inspired beach side hideaway. New LUX POOL HOUSE

Modern sanctuary
new 7400 residence. 8 bedrooms, 8.5 bath. open floor plan establishes an immediate connection between the living space and the outdoors. 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 As per Suffolk country requirements, No short term rentals, reach out for questions

Luxe Southampton Estate - Minutes to Village
Now renting for US Open & Summer - Minutes to Shinnecock Hills & Southampton Village. — Enjoy Summer at this luxurious, renovated 1.1 acre estate minutes from Village. This 6,000 sq ft home is conveniently located South of highway close to beaches, golfing, and bay. With six en-suite bedrooms and three powder rooms, this home is well laid out for fun and leisure. Featuring gym, outdoor deck, latest smart home / security tech, office, chef’s kitchen, and more.

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.
Popular amenities for Long Island luxury holiday rentals
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Hamptons • Waterfront Estate •
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