Luxury rentals in Long Island

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Top-rated luxury holiday rentals in Long Island

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Luxe

Home in Wainscott

Just completed Ultimate Wainscott Compound 6 Acres

Indulge in the ultimate summer getaway at your private 6+ acre oasis, where luxury meets breathtaking amenities. Enjoy a new 2025 tennis and basketball court, a large heated pool, outdoor living spaces, spa, fire pit, red light sauna, and more. The fully renovated 7-bed, 7-bath Post-Modern home offers sunlit interiors, soaring ceilings, sunroom, and a state-of-the-art lower level with endless entertainment. This rare retreat is perfect to unwind or play. Book your stay today! 3-day min. #16-2856

CleanlinessIndoor spacesHot tub

4.98 out of 5 average rating, 53 reviews

Luxe

Home in Sag Harbor

Charming Sag Harbor Home w/ heated pool

Escape to your private summer oasis in the coveted Sag Harbor. This newly renovated 5bd, 3ba home is a tranquil retreat on a quiet cul-de-sac. Unwind in the spacious, light-filled living areas, artfully designed with a blend of stylish midcentury modern and antique furnishings. Perfectly located, you are moments from village shops, renowned restaurants & beautiful beaches. Your serene escape awaits. ~Please note that the pool only open seasonally from Memorial Day - Weekend Labor Day weekend ~

Indoor spacesCleanlinessFamily

5.0 out of 5 average rating, 30 reviews

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

Charming, Beautiful, Close-to-All 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.

CleanlinessIndoor spacesHospitality

5.0 out of 5 average rating, 23 reviews

Luxe

Home in Hampton Bays

Hamptons Gem in Shinnecock Hills

A stunning fusion of modern design and a smart home in the heart of the Hamptons. Expansive windows and bi-fold doors invite natural light into the open living spaces, blending indoor and outdoor living. The chef's kitchen, outfitted with top-tier appliances and a sleek island, perfect for entertaining. This 4-bedroom retreat features 4.5 baths, a lavish primary suite with a spa-like en-suite bath. Outside, enjoy a heated pool, lounge area, BBQ and a spacious balcony with breathtaking views.

Indoor spacesCleanlinessAccuracy

5.0 out of 5 average rating, 15 reviews

Luxe

A light-filled great room features vaulted wooden ceilings and expansive views of the water through large sliding glass doors. A colorful bean bag contrasts with the neutral decor, complementing a modern dining area and an efficient fireplace set against a stone wall.

Home in Springs

Waterfront Oasis + Pool/Spa & Private Beach

Waterfront in East Hampton! This perfectly renovated 5br | 3.5ba modern home with frontage on 2 bodies of water, offers stunning views year round. Relax by the saltwater heated pool & built-in spa or cozy up by the mid-century fireplace. WALK TO OUR PRIVATE BEACH & enjoy our 7 bikes, 4 paddle-boards & 3 kayaks, or take in the sunset over the water while you prepare dinner in the fully stocked chef's kitchen. Designer furniture promotes indoor-outdoor living w/refined simplicity. RR-25-1186

Indoor spacesViewLong stay

5.0 out of 5 average rating, 10 reviews

Luxe

Home in Montauk

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

Indoor spacesCleanlinessBarbecue

5.0 out of 5 average rating, 45 reviews

Luxe

The exterior view showcases a serene pool surrounded by landscaped gardens. A spacious patio features a dining area under an umbrella, while the charming two-story structure is complemented by large windows and a manicured lawn.

Home in East Hampton

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 & child safety pool fence avail. Central AC. Outdoor shower. No pets, no smoking, no parties RR-26-365

Indoor spacesCleanlinessKitchen

5.0 out of 5 average rating, 25 reviews

Luxe

An aerial view of the Mid Century Modern home is showcased, surrounded by lush greenery. The spacious yard features a heated pool, deck chairs, and a large checkered game board. A shaded seating area is positioned nearby, offering a perfect gathering spot amidst the natural landscape.

Villa in East Hampton

SERENITY AT SHOREWOOD Pool is Open April 1 - November 1. Must be 25+ to book. Luxurious Newly Renovated Mid Century Modern Home in East Hampton! Peaceful and stylish with three bedrooms, 3 1/2 baths, spectacular great room, huge deck, heated pool and more, less than four miles to the heart of East Hampton Village, world renowned for its restaurants, shopping and ocean beaches. A designer-curated architectural gem! Kick back and relax in this calm, stylish space.

CleanlinessIndoor spacesBarbecue

4.97 out of 5 average rating, 74 reviews

Luxe

Home in East Moriches

9000ft Hampton Mansion Retreat Indoor Pool Suana

Enjoy this amazing retreat with a huge heated indoor pool and suana. Rain or shine cold or warm, bring the family to this 9000ft, waterfront mansion on 2+ acres. Massive yard, 6 bedrooms, 8 baths, indoor pool, sauna, media room, open loft like living/dining/kitchen. Renovated in June 2022. Designer furniture, 20+ ft ceilings, Sonos smart home, swing/play set, private dock, basketball court, volleyball, wine room, endless amenities.

Indoor spacesCleanlinessAmenities

4.93 out of 5 average rating, 132 reviews

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

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.

ViewIndoor spacesAccuracy

5.0 out of 5 average rating, 12 reviews

Luxe

Home in Shinnecock Hills

The J Luxury Villa: Poolside Retreat w. Sauna

The J Luxury Villa is an exquisite estate in an exclusive neighborhood in Southampton, NY offers an unrivaled setting for your next vacation or event. The J boasts impeccably landscaped grounds that exude timeless beauty & chic sophistication. Independent of your booking, and to complement your accommodations, we have partnered with GMC Estate Solutions to offer you Concierge and Private Gathering services.

ViewIndoor spacesQuiet

4.95 out of 5 average rating, 110 reviews

Luxe

Home in East Quogue

Luxury Hilltop Villa East Quogue Private Pool&Spa

Escape to a private resort on 1.6 secluded acres in East Quogue's exclusive Southampton Pines. This 4-bed, 3.5-bath estate comfortably sleeps 8. Enjoy elegant interiors, a chef's kitchen, gym, and media room. The outdoor oasis features a new saltwater pool, hot tub, full kitchen, and fire pit. Perfect for a luxurious Hamptons getaway with family or friends, offering unparalleled privacy and five-star comfort.

Indoor spacesCleanlinessAmenities

4.93 out of 5 average rating, 15 reviews