300 houses for rent in Tuckahoe, Southampton town Suffolk County New York

One half of private, Ram Island, offers a complete, self contained luxury resort experience. Stylishly restored on 15 acres, the main house centers around an antique windmill-. Now an elevated office-overlooks Sebonac Creek, the blue waters of Peconic Bay and the green hills of historic National Golf Links. The main house has lavish living areas coupled with soft finishes and fixtures. Featuring a glass dining room, 4 luxurious bedrooms and baths and a primary suite with roof deck with soaking tub. Across the path, a wellness building houses a yogau002Fexercise room, sauna and shower section, massage room, meditation roost, plus a kitchen, bedroom and bath. Perfect for entertaining with a full sized separate guest house. A boat house opens to the deep water dock with room for large vessels. A beautiful in-ground gunite pool, hot tub, fire pit overlooking the inlet and bay compliment the grounds with arbors, gardens, walking paths, and wide lawns. The ultimate vacation experience. Addit

One half of private, Ram Island, offers a complete, self contained luxury resort experience. Stylishly restored on 15 acres, the main house centers around an antique windmill-. Now an elevated office-overlooks Sebonac Creek, the blue waters of Peconic Bay and the green hills of historic National Golf Links. The main house has lavish living areas coupled with soft finishes and fixtures. Featuring a glass dining room, 4 luxurious bedrooms and baths and a primary suite with roof deck with soaking tub. Across the path, a wellness building houses a yogau002Fexercise room, sauna and shower section, massage room, meditation roost, plus a kitchen, bedroom and bath. Perfect for entertaining with a full sized separate guest house. A boat house opens to the deep water dock with room for large vessels. A beautiful in-ground gunite pool, hot tub, fire pit overlooking the inlet and bay compliment the grounds with arbors, gardens, walking paths, and wide lawns. The ultimate vacation experience. Addit

Southampton Retreat. Tucked away on 1.29 ultra-private acres in the heart of Southampton, this elegant 4-bedroom, 3-bath retreat is surrounded by world-class golf courses and pristine bay beaches. Designed for effortless entertaining, the home features sun-filled living spaces and a resort-style Gunite heated pool. Stylishly appointed throughout, it's the perfect Hamptons escape for Summer 2026. Including the U.S. Open season. Just 4 minutes from Southampton Village's acclaimed restaurants, chic boutiques, and stunning ocean beaches, this is a rare opportunity to experience Hamptons luxury at its best. Available June 14-21: $8,500 | July: $40,000 | July-LD: $85,000 | Aug: $42,000 | Aug-LD: $45,000

Outstanding water views! Come watch the leaves change while enjoying this beautifully appointed luxury townhome in a gated community with only 12 units. Condo has primary ensuite with balcony, secondary ensuite, an open concept living area with large balcony, finished lower level with sliders to patio and laundry room. There is also a clubhouse with fitness room and community pool. All this within close proximity to restaurants, shops, beaches and all the south and north fork have to offer. Easy commute with jitney and railroad close by. Additional information: Appearance: excellent

Available June and US Open 2026. Beautifully renovated in 2025 by a chic NYC designer, this bright and airy 3-bedroom, 2-bath home offers the perfect Hamptons escape. Set on a private acre abutting a 33-acre preserve in coveted Red Creek Ridge, it blends modern luxury with serene natural surroundings. Flooded with natural light, the open living room boasts cathedral ceilings, wood floors, and a cozy wood-burning fireplace. The stunning chef’s kitchen features a quartz island, new stainless-steel appliances, and a sunny dining area overlooking the grounds. The primary suite is a true retreat with a king bed, walk-in closet, and a spa-like bath with double vanity and walk-in shower. Two guest bedrooms—one with twins and one with a queen—share a beautifully renovated full bath. A separate family room with pull-out sofa provides the perfect spot for movie nights or working remotely. Step outside to enjoy resort-style living with an expansive deck for lounging and dining, a heated pool, hot

Experience Luxury & Privacy Rental Reg #: PENDING. A gated entry and long private driveway lead to this private and secure estate tucked away on 4.65+u002F. Manicured acres. 7,400+u002F. Sq. ft. Of thoughtfully designed living space on three floors offer ample space for gathering both indoors and out. A double height grand entrance opens to a spacious living room with fireplace and dining room. French doors lead to screened porch that overlooks the serene setting. Top of the line chef's kitchen is flooded with light and features premium appliances and an over-sized island perfect for cooking and entertaining. Six bedroom suites include an upstairs master with fireplace and balcony and a first floor junior master. Finished lower level offers a game room, gym, 2 bedrooms, 3 baths and a multitude of French doors. A brand new heated Gunite pool, pool house and all weather tennis court, round out the experience of luxury and privacy on a grand scale. Also available: Short-Term $75,000 Oct 1

Charming Westhampton Beach Summer Rental – Prime Location! Escape to your perfect summer retreat in the heart of Westhampton Beach, just 0.5 miles from Main Street and moments from Long Island’s most sought-after beaches. This immaculate 5-bedroom, 3-bathroom cottage offers the ultimate getaway, featuring a heated in-ground pool, outdoor shower, and a private pickleballu002Fbasketball court—all set within a secluded, beautifully landscaped property bursting with vibrant spring-summer blooms. Whether you’re looking to relax by the pool, enjoy outdoor activities, or explore the Hamptons, this home has it all. Availability: Spring Summer and Fall 2025

Available 2026: July @ $19,750; August @ $24,000; August-LD @ $27,000; July-Aug 31 @ $39,000; July-Labor Day@ $42,000 Heart of Westhampton Beach Village! This 3 bedroom, 2-1u002F2 bath charming Hamptons cottage, tucked away on a quiet lane, is located only a few blocks from Main Street shops, restaurants, the beautiful Sunset Movie Theater and Performing Arts Theatre, and minutes to the Ocean Village Beach. It's the perfect home for relaxing and entertaining with its private back yard, deck, heated pool and the spacious great room with fireplace, dining area and loft space. The open kitchenu002Ffamily room also has a sittingu002Ftv area at one end. Amenities include central air, oil heat, hardwood floors, jacuzzi tub

Enjoy the U. S Golf Open while staying nearby in this wonderful, newly renovated 4 bedrooms and 2 1u002F2 bathroom home situated with easy access to Southampton. The first floor features a large, bright living room that leads into the eat-in kitchen with light hardwood floors throughout the house, laundry room, half bath and a cozy den with fireplace completes the first floor. The second floor has a large primary bedroom, primary bathroom and three ample guest bedrooms and a guest bathroom. Spend your relaxing time in the private backyard with a salt water, heated pool and large patio area. Great for entertaining or visit Shinnecock Bay (. 7 mile) at the end of the road, Ponquogue Beach 3.5 miles away. This home is close to town, public transportation, restaurants, shops and Shinnecock Bay. US Open 2 week rental. 12,500 weekly July. 30,000 August thru Labor Day weekend. 30,000

Available: Short-term and Fully Furnished Welcome to 9 Pine Tree Road—a newly reimagined Hamptons retreat set within one of Southampton North’s most coveted waterfront communities, just moments from a private, residents-only beach. This exceptional four-bedroom, two-and-a-half-bath home has been fully transformed through a brand-new designer renovation, offering a refined blend of modern style, coastal charm, and effortless livability. The open-concept main level is bright and inviting, anchored by a sun-splashed kitchen and dining area where custom built-in bench seating wraps beneath oversized picture windows—perfectly framing the professionally landscaped backyard. Designed with both relaxation and entertaining in mind, the home transitions seamlessly to the outdoors, where a brand-new pool, elegant cabana, and fresh lush landscaping create a private resort-like oasis. Bedrooms are thoughtfully distributed across two levels, providing the ideal balance of privacy and connection for

Breathtaking sunsets and unobstructed views of Moriches Bay define this new, Custom-Designed, modern retreat! Floor-to-ceiling glass windows, seamless indoor-outdoor living, and a heated gunite pool create the ultimate Hamptons summer experience. Five ensuite bedrooms offer privacy and comfort for family and friends, including a stunning primary suite with spa-like bath, walk-in closet, and sweeping bay views. The first level features an open floor plan, gas fireplace, wet bar and sliding glass doors to the swimming pool, deck and outdoor dining area. A Peloton equipped fitness area and additional lounge space enhance the home's amenities. A private easement with walkway offers access to the ocean beach, completing the rare bay to ocean lifestyle. Conveniently located just minutes from Main Street, shops and restaurants, approximately 90 minutes from NYC and 10 Minutes from Gabreski Airport 2026: 2 Weeks: Sept 25-Oct 9 @ $24,000 and October 1-30 @ $30,000. 2027: July 1-July 30 @ $145,0

Discover your perfect getaway at this stunning 3-bedroom, 2-full-bathroom rental, ideally situated near the pristine shores of Goldsmith's Inlet Beach on the North Fork. Step inside to find a fully renovated interior that boasts high-quality finishes and contemporary design. The rental includes two expansive living rooms, with a 24 ft high soaring cathedral ceiling in the great room seamlessly connecting to the kitchen and dining room. The spacious open concept living area and expansive windows emanate natural light throughout and showcase serene waterviews of Goldsmith's Inlet. Each bedroom is equipped with a new Nectar Hybrid Premier mattress, complemented by high-quality bed linens and towels. The property also features an east-facing deck with a teak dining table and seating for six, perfect for al fresco meals, and a Weber BBQ for outdoor grilling. On the west-facing patio, unwind in the Bullfrog 7-person hot tub, rinse off in the hotu002Fcold outdoor shower, and enjoy beautifully

Free Standing Contemporary Home in desirable waterfront Community of Old Harbor Colony in Hampton Bays. Water views down the canal across the street as you sit in your beautiful sunroom or on your deck. The home has been completely renovated with Open Concept floor plan. Living room offers natural gas fireplace, new state of the art chef's kitchen, four bedrooms, two and a half baths (with the primary bedroom wu002Fbath on main level. Private association beach at the end of the street. Don't let this one slip away offered for for June, July, andu002For August. LD

September in the Hamptons! Traditional Post-Modern creekfront home offers privacy, water access and plenty of room to relax and entertain. Open concept living room, dining room & newly remodeled chef's kitchen. Main floor living spaces open to covered blue stone porch & pool area. Oversized, heated, saltwater pool. Four bedroomsu002F3.5 bathrooms, dedicated office, bonus denu002Ftv room. Direct creek access for kayakingu002Fpaddleboarding. Evening sunsets are incredible! Bed set up: (2) king beds, (1) queen, (1) full. Main floor bedroom suite with private bathroom and king size bed. Primary suite on second floor with private deck overlooking the waterfront. Attached 2 car garage. It's the perfect time to plan an extended stay in the Hamptons

Beautifully maintained 4-bedroom, 2.5-bathroom home nestled on a quiet block. Step onto the inviting front porch and into a residence that blends comfort with charm. The spacious backyard is perfect for outdoor games, lounging, or entertaining on the expansive deck outfitted with a dining area and outdoor living room area. A large pool adds to the summer fun, making this an ideal retreat. Conveniently located just 2.5 miles from the vibrant Village center, you'll enjoy easy access to shops, theaters, a farmers market, and a nice range of restaurants

Nestled in the charming Quiogue enclave of Westhampton Beach, this beautifully renovated shingle-style cottage offers the perfect blend of privacy, convenience, and coastal charm. Tucked away on a peaceful flag lot, the property enjoys a prime location just one-half mile to the Village of Westhampton Beach and only one and one-half miles to the ocean. A covered front porch welcomes you into a sun-drenched living room, creating a warm and inviting atmosphere. The thoughtfully updated eat-in kitchen is ideal for casual gatherings, while two comfortable bedrooms and a updated full bath provide easy, single-level living. The second bedroom includes a sleeper sofa and desk. Outside, the lushly landscaped backyard offers exceptional privacy and a serene setting to unwind after a day at the beach. Additional features include a garage, shed, and finished attic space for storage. Enjoy close proximity to the village's wonderful restaurants, boutique shops, farmer's market, performing arts cente

Pine Neck Landings, community perfection, 6 bedrooms 4 baths 2 living areas with an open floor plan, dining, 2 bedrooms on the first level one a junior ensuite primary, 4 additional bedrooms on the second level a gorgeous ensuite primary, finished basement for those rainy days. Great custom closets for your convenience. Other positives include stainless steel viking appliances a generous pantry, sonos and plenty of room to make your summer dreams come to life. Your outdoor experience is what you want in a summer rental, gorgeous heated pool, outdoor shower and plenty of relaxing spaces for lounging or dining. Available full season MD-LD, or July and August-LD

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

Beautiful Quogue South home set on a quiet private lane. The mahogany front porch with tranquil rocking chairs awaits. A refresh of new furniture, paint, rugs, and curtains was recently completed. The first floor is open and light filled and includes a living room with soaring cathedral ceiling and fireplace, a great room with chef's eat-in-kitchen and top-of-the-line appliances, a dining area, seaparte office, powder room, and laundry room. A first floor primary suite with a sitting area completes the main level. The second floor includes three en suite bedrooms and a fourth guest bedroom. The backyard hosts a heated gunite pool with blue stone patio and a 100 year old barn that has been restored for your entertainment. The barn includes a pool table and outdoor shower. Close by is the Quogue Village Beach

This Southampton beach house blends playful coastal personality with relaxed Hamptons living. Located in Bay View Oaks, a waterfront community with private beach access, deeded rights to Peconic Bay, and a boat launch, the home sits in a quiet setting within Bay View Oaks, just 10 minutes from both Sag Harbor and Southampton Villages. Inside, the home features high ceilings, light-filled rooms, and professionally designed interiors with a cool design sensibility that incorporates open-plan living, retro pop-culture touches, and colorful accents. The layout includes four bedrooms plus a bonus bunk room, 3.5 bathrooms including a primary ensuite, and multiple indoor-outdoor gathering zones that flow naturally for lounging, dining, and entertaining. A gourmet kitchen inside and out, multiple dining areas, and a layout arranged for smooth day-to-day living make the home easy to enjoy. The outdoor spaces offer a range of playful amenities. After the beach, rinse off sandy toes in the outdoo

Welcome to 420 Maple Avenue S. A sanctuary nestled in the heart of Flanders. This fully updated home offers a harmonious blend of comfort and style, set against a backdrop of natural beauty. With a vast expanse of preserved land as your backyard, you'll enjoy unparalleled levels of privacy and tranquility. The Home features three spacious bedrooms and three full bathrooms, providing ample space for relaxation and rejuvenation. The primary suite is a retreat within itself, offering generous space and a serene ambiance. The open floor plan allows for a natural flow between rooms, perfect for entertaining or simply enjoying day-to-day living. The Kitchen, complete with stainless appliances, opens onto a deck equipped with a BBQ, making it an ideal spot for alfresco dining or simply soaking in the natural surroundings. The property also boasts a large backyard, perfect for outdoor activities. In addition, the home boasts an oversized 6-car garage and a spacious driveway, to fully accommoda

Centrally located yet tucked away, this charming, sun-drenched Ranch home puts you at the center of it all. Perfectly situated South of the Highway, this home offers the rare combination of total privacy and incredible convenience. The property is just 1u002F2 mile from the LIRR, as well as the shops and dining of town, and a short drive to local beaches. Located less than 6 miles from the US Open Championship at Shinnecock Hills Golf Club in Southampton, this home offers a premier location for the tournament in June. June rental includes up to 2 weeks' stay. Enjoy the convenience of a short drive to the course while maintaining a peaceful retreat away from the event crowds. This one level home is designed for seamless indoor-outdoor living. The approximately 1,700 sq ft interior features a sprawling living room with a cozy fireplace and a wall of windows overlooking the grounds. With three bedrooms and two full baths, including a primary suite with sliding doors leading to an exhilara

Escape to the Hamptons and experience the perfect blend of refined luxury and laid-back coastal living in this beautifully designed, nearly new 5-bedroom, 4.5-bath home in prime south-of-the-highway Westhampton. Set on a private 0.57-acre lot with 4,050 sq. Ft. of living space, the home features designer finishes and experiences throughout, with carefully curated spaces created to relax, unwind, and entertain effortlessly. A bright, open layout showcases white oak floors, a gourmet kitchen, and seamless indoor-outdoor flow. Outside, enjoy a heated saltwater pool, covered porch for al fresco dining, and a grilling area perfect for summer evenings with friends. Inside, a first-floor guest suite and home office offer flexibility, while the spacious upstairs primary suite features a spa-like bath retreat. Just 2 miles to Main Street and 4 miles to Roger’s Beach, this is Hamptons living at its best—elegant, easy, and close to everything. This listing may include images that have been digita

Location! Location! Available for US Open. Just two short blocks from Southampton village's charming restaurants and shops and a short distance to the train and jitney stop, this pristinely kept traditional home offers a luxurious escape. Relax by the heated, gunite pool amidst manicured, flowering gardens or enjoy the spacious living areas inside, including a living room with two seating areas, a den with a fold-out sofa and large television, a formal dining room, and a bright gourmet eat-in kitchen with doors leading to the fabulous backyard. A large pantry and full bathroom complete the ground floor. Upstairs, three en suite bedrooms await, with the king-sized primary suite featuring a private balcony overlooking the pool and gorgeous grounds, and a second balcony shared between the two Queen-sized guest rooms. A stunning pool house with a living room, full bath, and kitchenette, and an outdoor shower enhances the home's unique appeal. The private grounds are perfect for entertainin

Immerse yourself in the tranquil charm of New Suffolk, a premier waterfront community where life moves at a more graceful pace. This sophisticated 4-bedroom, 3.5-bathroom retreat is perfectly positioned for those who want to experience the quintessential North Fork lifestyle—from scenic bike rides to world-class vineyards. Leave the car behind and stroll to local mainstays like Minnow, Peeko Oysters, and Legends. For a true taste of the region, take a leisurely ride to the renowned 8 Hands Farm for a farm-to-table experience, Wickham’s Fruit Farm for fresh peaches, or pick up the morning’s catch at Braun Seafood. Inside, the home unfolds into a bright, expansive sanctuary. Floor-to-ceiling windows bathe the living area in natural light, creating a seamless connection to the outdoors. The layout flows effortlessly into a gourmet kitchen, specifically designed for hosting intimate gatherings or crafting meals with local farmstand finds. High-end finishes and modern amenities throughout e