luxury real estate for rent Southampton, United States

Single story waterfront home offering 3 bedrooms, 2 baths & South of 27! [[Rental Registration # 241322]] EH RR #: 241322 Rental Terms: August - Labor Day: $30,000 July: $22,000 Other / Short Term - Year Round: $80,000 Winter Season: $4,100 Per Month July - Labor Day: $55,000

This exceptional residence is ideally situated near to Shinnecock Bay and only moments from the ocean. Enter through a welcoming foyer into a light-filled, open-concept living space featuring a fireplace and a striking custom paneled ceiling. The thoughtfully designed eat-in kitchen is fully equipped and seamlessly connected to the dining area, creating an inviting setting for both everyday living and entertaining. The first floor offers a well-appointed primary suite with private bath, an additional guest bedroom, a full bathroom, a cozy library or sitting nook, a laundry room, and a powder room. Throughout the home, exquisite marquetry craftsmanship, stained glass windows and panels, and curated artwork highlight the home’s unique character and attention to detail. Upstairs, the second level provides two additional guest bedrooms and a full bathroom. A covered walkway connects the main house to an impressive 20’ x 50’ indoor, ozone-treated swimming pool, complete with a full bath and sauna—perfect for relaxing on rainy days or unwinding after a day at the beach. Outdoors, a private inner courtyard patio with pergola offers multiple spaces for al fresco dining and lounging, along with a barbecue area ideal for hosting family and friends. The fully finished lower level adds even more versatility, featuring a full gym and dedicated Pilates room. The private backyard setting invites evenings gathered around the fire pit after days spent by the bay or ocean. The home also includes bikes, kayaks, and a small boat, making it an ideal retreat for outdoor and water-sport enthusiasts. All of this is just a short drive to the shops, restaurants, and entertainment of Hampton Bays and Southampton. Available for summer and even a potential US Open stay. MD-LD: $85,000, July-LD: $65,000, Aug-LD: $35,000, Short Term: $20,000.

Located just outside Bridgehampton village sits this quiet cottage available for summer and off-season rental. Tasteful amenities include a large living room with fireplace and vaulted ceiling, a separate kitchen with washer/dryer, a dining area, two bedrooms and a full bath. A charming patio allows for outdoor nature enjoyment, all within minutes of local area shops, restaurants and ocean beaches. [[Rental Registration # RP241102]] EH RR #: RP241102 Rental Terms: Winter Season: $30,000 Per Month June: $15,000 Memorial Day - Labor Day: $60,000 July: $25,000 July - Labor Day: $50,000

Escape to the serene charm of New Suffolk this summer with this beautiful rental property! Offering ample space for all, this delightful home boasts 5 bedrooms and 3 bathrooms, ensuring everyone's comfort. Step outside onto the expansive wrap-around patio, perfect for summer evenings and al fresco dining. An outdoor shower provides a refreshing touch after a day at the beach, and the large, lush yard offers plenty of space for recreation and relaxation. Whether you're a culinary enthusiast grilling up a feast or simply enjoying the company of loved ones in the spacious kitchen, this home is designed for entertaining and creating lasting memories. Nestled in the coveted New Suffolk community, you'll be just moments away from the area's most stunning beaches. Embrace the quintessential summer lifestyle in this lovely retreat, where comfort and convenience meet coastal charm.

**2026 Rates** May $15K, June $18K, September 8-30 $12K, October $12K. This property is a stunning waterfront home located on West Cove in the exclusive Nassau Point area. Offering breathtaking views of the Great Peconic Bay, Robins Island, and New Suffolk, this home exudes charm and sophistication. The main level boasts two spacious great rooms, an enclosed three-season room, an eat-in kitchen, a dining room, and a primary en-suite bedroom. The finished basement includes two additional bedrooms, a full bathroom, and a media room, while the second floor features two more bedrooms and another full bathroom. The property's grounds are beautifully landscaped and elevated, with a mahogany deck, stone patio, outdoor dining area, and stairs leading to a raised platform beach with a pergola, providing easy access to the Bay for a refreshing dip.

2025 Rates: June $8K, July $12K, A1-LD $13K, September $8K, October $7K Charming Nassau Point Cape Cod. Enjoy sprawling private grounds with community beach access as you enjoy the summer months in this ideal 3 bedroom 2 bathroom escape. The main level features and open dining/, kitchen leading to wood deck, main floor bedroom, full bathroom and living room. The second floor features 2 additional bedroom and 1 full bathroom. Don't let this amazing East End retreat slip away!

Available 2025: April: $12,000, May: $17,500, June: $22,500, July: $35,000. Vacation at this spectacular, completely renovated 4 en suite bedroom home this summer located in the desirable Fleet's Neck neighborhood with 2 gorgeous beaches moments away! Entertain in the open concept living area featuring a large island overlooking the family and dining area, perfect for large gatherings. The first floor features 2 bedrooms with 2 full baths with glass sliders leading out to the deck. Downstairs has 2 more ensuite bedrooms with glass sliders leading out to a patio. Soak up the sun and relax by the saltwater pool, rinse of the sand with the spacious outside shower or enjoy the patio where there is plenty of room to entertain throughout any time of the day.

Spend the last weeks of summer on the water at this beautiful bayfront getaway. This home offers 4 bedrooms and 2 bathrooms with stunning views of the Peconic Bay and direct access to everything the North Fork has to offer. The home features bright, comfortable living spaces designed for easy summer living, with panoramic water views and room to relax both inside and out. Whether you are entertaining, kayaking, dining al fresco or simply unwinding by the bay, this property captures the best of North Fork waterfront living. Available August 15th through the end of August, with the possibility to extend through Labor Day. Rare opportunity to enjoy prime North Fork waterfront living during the best part of the season.

Escape to your own piece of paradise in this stunning bayfront home, offering the ultimate in relaxation and luxury. Nestled on the scenic North Fork, this charming 4-bedroom, 2-bath residence boasts breathtaking bay views and direct access to your very own private beach. Imagine unwinding on the expansive deck, sipping your morning coffee while gazing at the tranquil waters, or heading down to the beach to dip your toes in the sand. This home is a true oasis, perfect for outdoor entertaining and water activities. Whether you're swimming, kayaking, paddleboarding, or simply lounging on the giant anchored raft, there's something for everyone. The lush, hydrangea-filled gardens provide a sense of privacy and serenity, making this retreat incredibly enticing. With two spacious living areas and options for dining indoors or out, this home is designed for both relaxation and entertainment. Enjoy cozy evenings by the beach or star gazing, roasting marshmallows over a fire and making memories to last a lifetime. Discover the perfect North Fork getaway, where charm, character, and coastal living come together in harmony. Permit # 24-3065

Offered as a Year Round Rental! Welcome to 435 Lupton Point Road, a beautifully appointed coastal residence tucked within a private Mattituck waterfront community offering direct water access to Deep Hole Creek and a private dock. Spanning approximately 2,700 square feet, this thoughtfully designed home features a spacious open floor plan ideal for both everyday living and entertaining. At the heart of the home is a chef’s kitchen, complete with generous counter space and seamless flow into the dining and living areas. A wood-burning fireplace anchors the living room, creating a warm and inviting atmosphere year-round. The home offers four well-proportioned bedrooms, two and a half bathrooms, and a dedicated home office, providing flexibility for remote work or guests. Natural light fills the interiors, enhancing the home’s airy coastal feel. Step outside and enjoy the rare convenience of water access with a private dock, perfect for boating, kayaking, or simply enjoying the peaceful creekside setting. The property’s location offers the best of North Fork living—just minutes from Love Lane’s shops, cafes, and farm stands, as well as New Suffolk Beach, making it an ideal full-time residence or weekend retreat. A unique opportunity to enjoy privacy, water access, and timeless North Fork charm in one exceptional offering.

Stunning Renovated Craftsman in Nassau Farms – North Fork Summer Retreat- Enjoy the perfect North Fork escape in this pristine, renovated Craftsman home located in desirable Nassau Farms, just moments from Nassau Point Beach. Designed for relaxed summer living, the bright and airy great room features an open-concept layout filled with natural light. The chef’s kitchen is beautifully appointed with granite countertops, custom cabinetry, and high-end appliances — ideal for entertaining family and friends. Lovely Primary en-suite with 2 additional guest bedrooms. Step outside to your private backyard oasis complete with a bluestone patio, built-in outdoor sound system, stone fireplace, and full outdoor cooking area. Whether you’re hosting sunset dinners or enjoying quiet evenings under the stars, this home delivers the ultimate vacation experience. A private path offers easy access to nearby kayaking, and you’re conveniently close to all North Fork attractions including beaches, wineries, farm stands, and charming local shops. Available Summer 2026 -( June – $10K , July – $15K, September – $15K. Off-season rates available upon request. Permit #0283

Lovely downstairs corner unit located across from the Sag Harbor Cove. There's one bedroom, one bath, laundry, a galley kitchen and nice covered patio. Now available for a winter rental. [[Rental Registration # R24-0012]] EH RR #: R24-0012 Rental Terms: Winter Season: $26,000 Per Month

Settle into summer on the North Fork in this beautifully maintained and updated 4 bedroom, 3 full bath home located in the Angel Shores community of Southold. The layout is ideal for entertaining or just enjoying the lazy days of summer. This special home offers a 1st floor bedroom and full bath, along with a 2nd story spacious primary en-suite and 2 additional bedrooms to comfortably accommodate guests. Angel Shores is known for its sandy Peconic Bay beach, just a short stroll down the road, perfect for easy beach days and watching sunsets by the water. The home is also conveniently close to Southold’s wineries, farm stands, and village amenities, putting the best of the North Fork right at your fingertips. 2026 Availability: June 16-June 30th $7,000, July $23,000, August $25,000 August-Labor Day $27,500. Permit # 0956

No expense was spared on this Brand-New, 10,000+/- sq. ft. gated, Custom Construction. Available for the first time for June/July, 2024. This is perhaps the nicest estate rental offering available just outside Sag Harbor Village, only a 1/2 mile to Long Beach. The home itself is magnificent, custom designed, with no detail overlooked. It has every amenity--7 ensuite bedrooms, elevator, magnificent custom-designed Kitchen, glass Breakfast Room, oversized Great Room and Living Room with Wet-bar. The first floor also features a luxurious Bar Room/Butler's Pantry and a large 1st-floor Office with TV. The lower level offers a Gym, Game Room, and Hotel-like Spa, with Steam Shower, Soaking Tub, Shower, and Sauna. The majestic property offers 1.5+/- acres of full lawn--gated and fully enclosed. It includes a Pickleball Court, Basketball, 45' Pool, Hot Tub, Outdoor Living Room, and Outdoor Kitchen/Bar. The property is perfect for family outdoor living and entertaining. And for local daily activities, the offering is also only moments to Community Tennis, two gorgeous Beaches, Sag Harbor Marinas and the Shelter Island Ferry. Rental Terms: September: $48,000 September/October: $65,000 Other / Short Term - Year Round: $650,000 November: $30,000 Winter Season: $135,000 Per Month

Set along the sandy shores of Quogue Beach, 174 Dune Road is a rare oceanfront offering with sweeping Atlantic views and easy access to everything the Hamptons has to offer. The main level has an open, airy layout with oversized windows that bring in natural light and frame the water views. The kitchen flows into the dining area and living room, where a sunken fireplace nook creates a cozy spot for gathering. The home’s octagonal design adds architectural interest and a great sense of space. The primary suite features dramatic ocean views. There’s room for everyone with additional bedrooms and three bunk rooms, making it ideal for entertaining family and friends. Outside, the deck offers plenty of space for dining, relaxing, or soaking in the sea air. The property also includes a private tennis court.. Available for the U.S. Open as a 2-week rental, or by month with June, July, and August through Labor Day, all offered individually. The property is also available for the full season (Memorial Day through Labor Day).

Discover the finest rental that Quogue Village has to offer. A Contemporary with Zen vibes, offering 5 bedrooms, 5.5 baths an open floor plan that opens to a dining room to entertain over 10 guests. Chef's kitchen has 2 ranges, a 4-burner gas range and a Viking 6 burner gas range, sub-zero refrigerator, 2 dishwashers, and of course, a wine refrigerator. To top it?off, an island with seating for 6 adds more entertaining space. First floor ensuite bedroom, second floor, primary ensuite with private balcony, designer bathroom with soaking tub, walk-in shower. The fully furnished lower level offers media room, full scale gym, and wet bar. Outside enjoy the heated Gunite pool, tennis, and a hard court with basketball hoop. the 16x16 gazebo offers a fireplace for those special evenings in the Hamptons. Option to rent mini moke for those drives to the exclusive Quogue Village Beach. What a spectacular summer in Quogue. Available July 2026 only

Impressive Goose Creek home with water views and large heated in-ground pool! This four bedroom, three bath house features a first floor primary bedroom with en-suite, a gourmet kitchen and open living space. The newly designed landscape with outdoor kitchen (not pictured) is ideal for entertaining or relaxing. Enjoy its large fire pit and BBQ grill after an afternoon of Kayaking. Close to Southold town and Corey Creek Beach. 2026 Pricing: July $30K , Aug-LD $35K

Classic Cape Cod Retreat Near Shell Beach Enjoy summer on Shelter Island in this charming Cape Cod–style home with tranquil water views just across the street and easy access to one of the island’s most popular beaches. Located less than half a mile from Shell Beach, this 4-bedroom, 2.5-bath home is set in a friendly, sought-after summer community. The bright, open living and dining area flows seamlessly to a spacious deck, making it ideal for outdoor dining, entertaining, or relaxing after a day at the beach. The spacious kitchen features warm oak cabinetry with white countertops, offering a classic, functional layout that complements the home’s Cape Cod style. The first-floor primary bedroom provides a private and comfortable retreat, ideal for easy living and added convenience. Upstairs, three additional bedrooms offer plenty of space for guests. With nearby beach access, and island activities that Shelter Island has to offer, this home is a wonderful seasonal escape for relaxed coastal living.

Your quintessential North Fork summer starts here. Tucked away in the quiet beach community of Paradise Shores, this Bayfront cottage is the summer retreat you’ve been dreaming of. Positioned directly on Southold Bay with unobstructed views of Shelter Island, this charming cottage offers the best scenery on the North Fork. Whether you're hosting a sunset dinner or just enjoying a quiet morning, the backdrop is always spectacular. Loaded with vintage charm and coastal energy, it’s a place where the days are measured by the tides rather than the clock. The first floor features a waterfront sunroom, cozy living room, galley kitchen, two bedrooms and a full bath. For ultimate privacy, escape to the second floor, featuring a primary suite with a dedicated sitting area -the perfect perch for morning coffee- and half bath. Step outside to your own secluded paradise where you will find a waterfront deck offering the perfect space for al fresco dining, stargazing, or simply watching the boats pass by. It’s the ultimate front-row seat to the island's beautiful golden-hour. This property has all the markers of a perfect North Fork getaway. Permit #1435. Available Memorial Day-June 30: $18,000, July 1-31: $20,000 and August 1-31: $25,000.

2026 Rates: NO AVAILABILITY New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with Chef's Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal dining room. All four bedrooms are located on the second level: 1 Primary En-suite, 1 Junior Suite, 2 Guest Bedrooms and Full Hallway Bathroom. You will enjoy being within close proximity to Goose Creek, South Harbor Park Beach and Southold's vibrant business district!

Spend your summer in the heart of Westhampton Beach at 9 Ocame Avenue — a chic, four-bedroom, three-bath retreat designed for effortless coastal living. This bright and stylish home offers the perfect blend of charm, comfort and Hamptons convenience, all moments from Main Street, world-class beaches, boutiques and dining. Step inside to sun-filled living spaces, a well-appointed kitchen, and comfortable bedrooms ideal for hosting gatheirngs. Outdoors, enjoy everything that makes summer special: a welcoming front porch, patio for dining and lounging, sparkling pool, pool house and a refreshing outdoor shower for after beach. Available June, July, and August, this home is an exceptional option for those coming out for the U.S. Open in June—providing the perfect Hamptons home base within close reach of Shinnecock Hills and all the excitement surrounding tournament week. Available 2026: June-July $52, June $20k, July-LD $70k, July $34k

Offered June $15,000; July $25,000; August $30,000; September $20,000; October $15,000. This contemporary waterfront home on Great Pond enjoys sunrise over the water and spectacular sunsets over Long Island Sound from its hilltop setting in one of the North Fork’s most distinctive beach communities. Surrounded by native plantings and filled with natural light and cooling breezes, the home is designed for effortless indoor-outdoor living. Spanning three floors and 2,600 square feet, it features 3 bedrooms, 4 full baths, and multiple spaces for gathering, entertaining, or quiet retreat. Enter from the spacious front deck, with seating for four and views of lush natural landscape and Sound. The main level comprises an open-plan living room with a wood-burning fireplace, dining area, eat-in kitchen, TV room, full bath, and a rear deck with dining table for six overlooking Great Pond. The ever-changing landscape of water, sky, and birdlife makes this a haven for nature lovers. Upstairs are two ensuite bedrooms, both enjoying beautiful water views and brand-new bathrooms, the one in the master suite benefiting as well from a long bathtub. The garden level offers a third bedroom, full bath, laundry area, movie and screening room, and an office/den with glass doors opening onto a rear deck with lounge chair, sauna, and outdoor shower. A private path leads directly to Great Pond, where kayaks and a canoe await exploration. Additional amenities include bicycles, a massage chair, piano, binoculars, telescope, and EV charger. Kenney’s Beach and the beloved Little Fish restaurant are just a short bike ride away, creating an exceptional blend of comfort, privacy, and outdoor adventure in the heart of the North Fork.

Discover the perfect island getaway in this spacious 4-bedroom, 2-bathroom home tucked away on a large, serene lot. Surrounded by mature landscaping, the property features a generous front porch overlooking a peaceful pond—an ideal spot for morning coffee or sunset relaxation. Inside, the home offers a bright and inviting layout with a well-appointed kitchen complete with a center island, perfect for entertaining. Additional conveniences include an in-unit laundry room, mudroom, and a flexible bonus space great for a home office or playroom. A two-car garage provides ample storage and parking options. Located just minutes from Route 114 and South Ferry, the home offers easy access to all the island’s main destinations. Wades Beach is only 1.5 miles away, making beach days effortless. Guests also enjoy seasonal access (July 4th–Labor Day) to the Coecles Harbor Marina pool for added summer enjoyment. This peaceful retreat combines comfort, privacy, and convenience—ideal for your next stay on Shelter Island.