luxury real estate for rent Southold, United States

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.

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.

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

Ground floor one bedroom apartment in Driftwood Cove, steps outside of Greenport Village. Newly renovated with new floors throughout, refreshed kitchen with new stove & refrigerator, freshly painted. Living/dining room with coat closet, bedroom with walk-in closet, full bath, AC. Community laundry with new washing machines & dryers, parking lot. Close to Greenport Village shops, restaurants, groceries, Mitchell Park, waterfront wharf, high school, Jitney, LIRR, and bay beaches. Maximum occupancy 2, no pets, minimum FICA score 650. Driftwood Cove rental application required including background and financial checks. Subject to Board of Director’s approval.

2026 Rates: A1-LD $17,500, September $6,500, 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!

**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.

2026 Rates: April $7,500; May $12K; June $15K; July $25K; A1-LD $27,500; Sept $12,500; October $10K: This beautifully curated home away from home, blends modern design with warmth and style. Experience elegant comfort in your private retreat with natural light, modern decor and thoughtful touches throughout. Nestled on a quiet, tree lined street, this special haven features a front porch, fully equipped open kitchen, and spacious backyard with a pool and fire pit. Enjoy all season living in this home away from home just a 10 minute walk to The LIRR station, Hampton Jitney, and The North Ferry.

Sound Front Contemporary Octagonal Home with Private Beach. Contemporary and chic, mint condition 1970's modular octagonal home located on a breath-taking sound front walk-out private beach in Orient. Three bedrooms, each with a full bath and an additional powder room. Updated kitchen and bathrooms. Every room is furnished with period mid-C style furniture. Living room has original Malm wood burning fireplace. Many spacious common areas, including glazed porch connecting the two octagonal wings. Relax on the large water-side deck with hot tub while enjoy panoramic water views from every room. Offered June $15,000; July $35,000; Aug $35,000; Sept $20,000. Permit #0465.

Waterfront retreat in the coveted Fleets Neck community of Cutchogue. Nestled along a tranquil creek, this charming 2 bedroom, 2 bathroom cottage offers a peaceful setting with beautiful water views, spectacular sunsets, and the perfect backdrop for a North Fork escape. Enjoy kayaking, paddleboarding, fishing, or simply relaxing by the water, all while being moments from the neighborhood’s beloved beaches. Located within the sought-after Fleets Neck community, tenants can enjoy proximity to Fleets Neck Beach and Pequash Beach. Ideally situated near renowned vineyards, farm stands, waterfront dining, marinas, and all the charm of North Fork living, this inviting cottage offers the perfect blend of waterfront serenity and convenience. Available for September and October 2026, as well as an off-season rental opportunity. Whether you’re seeking a fall getaway, seasonal retreat, or extended stay on the North Fork, this waterfront cottage is a rare opportunity to experience the best of Cutchogue’s coveted Fleets Neck waterfront lifestyle. Availability: September $3,000, October $3,000 or off season rental for $2800 per month

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.

2026 Rates: August 1-15 $25,000: Escape to this exceptional seasonal rental, perfectly situated on the shores of the Long Island Sound. This beautifully appointed waterfront home offers the ultimate coastal living experience, featuring private stairs leading directly to the beach, an in-ground heated gunite pool, and panoramic water views from nearly every room. With 4 spacious bedrooms—including a luxurious primary en-suite—and 3 full bathrooms, there’s plenty of room for family and guests to unwind in comfort. The heart of the home is a dramatic post and beam Great Room, designed for both relaxing and entertaining, with soaring ceilings and expansive windows that flood the space with natural light. Step out onto the large balcony to take in sweeping views of the Sound, enjoy morning coffee as the sun rises over the water, or end the day with a spectacular sunset. Additional amenities include a 1-car garage, central air, and thoughtfully landscaped grounds that ensure privacy and tranquility. Whether you’re lounging poolside, walking along the shoreline, or enjoying evening breezes from the balcony, this home offers an unforgettable seasonal escape.

2026 Rates: $45,000 for Memorial Day Weekend-Labor Day: Welcome to 619 Bailey Avenue, a fully restored and turnkey farmhouse ideally located on the fringe of Greenport Village. Once part of a historic North Fork farm and estate, this circa 1900 residence has been thoughtfully reimagined to offer the perfect blend of classic charm and modern comfort for a summer escape. Original details—including hardwood floors, custom millwork, and timeless architectural elements—have been beautifully preserved, while stylish updates throughout create a relaxed and functional living environment. The custom chef’s kitchen is a true centerpiece, featuring a 48” range, oversized island, bespoke cabinetry, and an 8-foot bi-fold glass door that opens to the backyard for effortless indoor-outdoor living. The first floor offers a spacious living room with wood-burning fireplace, formal dining room, dedicated home office, powder room, and a flexible bedroom or bonus space. Upstairs, you’ll find two guest bedrooms and a full bath, along with a sun-filled primary suite featuring vaulted ceilings, a large walk-in closet, and a spa-like en-suite bath with double vanity and dual-head walk-in shower. Set on a generous and private lot, the backyard provides ample space to relax and entertain, complemented by a detached one-car garage. Enjoy close proximity to Greenport Village, Kontokosta Winery, nearby bay and Sound beaches, and local favorites like Sep’s Farm Stand—making this an exceptional North Fork summer retreat.

In our beloved 2,350 acres of Mashomack Nature Preserve, there are a handful of residences. At the end of this long private road through this preserve, one can find this breathtaking newly constructed modern home with no details left behind. This expertly crafted home is loaded with premium amenities, top-of-the-line appliances, and walls of windows overlooking Coecles Harbor, this home has no comparisons. With 3,800 sq. ft., the home features an open floor plan with sweeping water views from every vantage point, whether dining, cooking, or lounging. Continue entertaining outside on the large outdoor waterfront deck where you become one with nature. The master and one of the guest bedrooms are en-suite, and the 2 additional bedrooms share a bath. All the bedrooms have abundant closet storage. Enjoy this newly constructed private waterfront property this summer!, Additional information: Cooling:SEER Rating 12+

2026 Rates: May $26,000; June $29,000; July $36,000; September $27,000; October $24,000. Experience North Fork summer living in this newly constructed gem! Nestled in the sought-after Stirling Eastern Shores community, this impeccably designed modern farmhouse offers exclusive access to a private Long Island Sound beach, just a five minute walk from the property. Step inside to discover a light-filled and meticulously styled interior adorned with contemporary finishes and furnishings. The heart of the home is the chef's kitchen seamlessly integrated into the Great Room and anchored by a cozy gas fireplace. On the first floor, you'll find a convenient half bath, a junior en-suite bedroom, a spacious mudroom, and a sizeable 2-car garage. Ascend to the second level to encounter two additional guest bedrooms sharing a full bathroom, along with a stunning primary en-suite bedroom. The primary bath boasts a luxurious double vanity, a walk-in shower, a soaking tub, and an expansive walk-in closet for added convenience and indulgence. Outside, the property showcases a captivating landscape featuring a sprawling stone patio enveloping a 20x40 heated salt-water pool, complemented by an outdoor shower - an ideal setting for hosting gatherings and enjoying the summer sun.

2026 NO LONGER AVAILABLE; 2027 RATES COMING SOON This substantial post-modern residence offers the perfect North Fork retreat for those seeking space, comfort, and effortless entertaining. From the moment you enter, the home’s expansive layout welcomes you with bright, open living areas designed for relaxing and hosting with ease. With five generously sized bedrooms and three well-appointed bathrooms, there is plenty of room to accommodate guests throughout your stay. Inside, the home features beautiful hardwood floors, detailed custom moldings, and two inviting fireplaces that create a warm and refined atmosphere. Multiple living spaces allow guests to gather comfortably or enjoy quiet moments throughout the home. Step outside and experience a truly exceptional outdoor setting designed for summer living. The backyard is centered around a heated 20' x 44' saltwater pool w/ electric cover and surrounded by multiple outdoor dining and lounging areas perfect for entertaining, relaxing, and enjoying long summer evenings. Whether hosting a casual poolside barbecue or an elegant outdoor dinner, the setting provides the perfect backdrop for memorable gatherings. This property offers the ideal combination of space, comfort, and resort-style outdoor living—perfect for enjoying the very best of the North Fork.

2026 Rates: July 20-31; A1–LD: $22,500; Sept 1–30: $7,500; October: $7,500: Pristine Mid Century Modern Waterfront with 200' Of Private Sugar Sand Beach on sprawling 2 acre parcel! Property Features Breathtaking Views Of Robins Island, Southampton And Nassau Point. Chic Furnishings Adorn This Lovely Home Along with Interior Panoramic Views Of The Great Peconic Bay. Open Living Space with High Ceilings, Primary Master Suite, 3 Additional Bedrooms, An Eat-In Kitchen And an additional 2.5 Baths. If you're looking for privacy, ideal water access and one of the best location the North Fork has to offer, this is not to be missed!

Welcome to 15 Lake View Court in Southampton, a fabulously reimagined pond front home. The vibe is lux organic, the palette soothing. With water-views from every room, it’s easy to embrace the Zen aesthetic. This east-west facing three bedroom, three bath has space to spread out, yet is ideal for gathering together. The upper level features a kitchen, dining, and main living areas, from which you can walk out and enjoy the deck overlooking Little Fresh Pond. This outdoor space is ideal for dining, gathering or relaxing. The lower level enjoys 3 spacious bedrooms with sublime pond views, sumptuous bedding and 2 additional baths. The fully landscaped and irrigated property offers privacy, a path to the water, a private dock, and of course a fire pit. Complete with water toys and fabulous proximity to both Southampton Village and Sag Harbor, this is a sought-after home away from home.

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.

Offered July $35,000; Aug $35,000; Sept $25,000; Oct $20,000. Elegantly renovated and exceptionally spacious, this contemporary retreat is nestled within a parklike setting of sweeping lawns, lush gardens, and mature landscaping that affords remarkable privacy. Refined outdoor amenities include a heated gunite pool, outdoor shower, firepit, and walking path to abutting Island’s End Golf & Country Club. The main house and annex are filled with natural light, featuring soaring ceilings, oversized windows, and glass doors that open seamlessly to two expansive decks for effortless indoor-outdoor living. A generous poolside patio offers additional space for lounging and entertaining, while the decks provide inviting areas for alfresco dining, grilling, and relaxation. Bedrooms are thoughtfully positioned to ensure comfort and privacy for guests. Peaceful and secluded, yet just moments from Greenport Village, Seps Farm Stand, and sound and bay beaches, this home is impeccably suited for gracious North Fork entertaining.