luxury houses for rent Orient, United States

Available Seasonally June 20K, August 16th-Labor Day15K, Available September 15K and October 15K TIMELESS TRANQUALITY ON GARDINERS BAY - An inviting seasonal beachfront retreat on Gardiners Bay, thoughtfully designed as a peaceful escape from the demands of everyday living. Begin your mornings with beautiful sunrises over the water and settle into the quiet rhythm of bayfront living throughout the day. The home offers an open airy layout with three full sized water-facing bedrooms, updated fully equipped kitchen and baths and comfortable modern amenities throughout. A generous enclosed porch provides a versatile space for dining, working remotely or simply slowing down. Outdoors, a charming portico invites alfresco meals with a gas grill while an outdoor shower completes the experience– an effortless calming setting for refined yet relaxed bayfront living. Fully furnished and equipped with necessary linens and towels. Close to fine dining, golf and a versatile selection of wineries for additional enjoyment and entertainment.

2026 Rates: June $8,500/week; July and August $10,000/week (Two Week Minimum For All Rentals). Spend your summer in style at this exquisite brand-new modern farmhouse, offering the perfect blend of luxury, comfort, and North Fork charm. Located just minutes from Greenport Village, local farmstands, renowned wineries, and pristine beaches, this home is the ideal summer retreat. Set on a full 1-acre lot, this spacious and sun-filled residence features an open-concept layout with elegant hardwood floors throughout. The heart of the home is a high-end chef’s kitchen, fully equipped for entertaining and flowing seamlessly into a stylish living area complete with a gas fireplace—perfect for unwinding after a day on the Sound. The first-floor primary ensuite bedroom offers a serene private escape, while the second floor includes a junior ensuite and two additional guest bedrooms with a shared full bath—providing ample space and comfort for family and friends. Step outside to your own private oasis featuring a 20x40 heated in-ground pool, surrounded by lush landscaping and plenty of space for outdoor dining and lounging. Whether you’re sipping wine under the stars, enjoying a day at the beach, or exploring nearby Greenport’s vibrant shops and restaurants, this stunning farmhouse offers the ultimate summer experience.

Bright and spacious Contemporary summer rental on the North Fork. Featuring floor to ceiling windows, great room, 6 bedrooms, 3.5 bathrooms, eat-in kitchen, recreation room. Private back yard with 40x20 salt water heated pool. Offered June $25,000; July 1-23 $27,000 (RENTED); Aug 1-15 $20,000; Sept 9-30 $18,000. Permit #1230.

Not available for year round rent at this time. Newly renovated three bedroom, two bath bungalow just outside of popular Greenport Village. This house provides a sense of privacy and relaxation close to the beach. Located less than one mile away, the captivating Rocky Point Beach is a picturesque retreat for everyone to enjoy. Additionally, there is the exquisite Truman's Beach nearby, which provides a stunning view of Connecticut. Lavender Bay and Sep's Farm are conveniently located only 0.4 miles away. The exterior of the property is designed for entertainment, featuring a spacious patio, barbecue area, fire pit, and even an outdoor shower to refresh after a dip in the nearby beaches. Seasonal Rates: June $6,000 | July $8,000 | Aug-LD $10,000

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.

Rental is Available in 2026: August $75,000. Located 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!

A stunning architectural jewel in Pandion, this freshly built, never-before-lived-in residence is both design-forward and deeply inspiring. Clad in arctic pine tongue-and-groove and corten steel, its twisted gable form captivates from every angle, while exterior decking invites you to soak in the surrounding natural beauty. The design/build owner's home draws inspiration from exposure to Frank Gehry's artist friends' homes in Venice, California. Founded in 2003 by Alexandra Hayden, Octave Studio is known for creating intuitively designed spaces that balance comfort and creativity, honoring the architecture and natural surroundings while reflecting each client's unique spirit. Curate | Build is Shelter Island's premier general contractor, known for high-end residential construction and renovations that blend timeless design, modern function, and uncompromising craftsmanship. The plywood-finished walls pay homage to Sea Ranch and early Gehry Venice architecture, creating a warm yet modern atmosphere that balances precision with artistry. Inside, radiant Indian black limestone floors anchor the soaring, cathedral-height living space centered around a wood-burning fireplace. The kitchen is as stylish as it is functional, featuring a Wolf range, Thermador under-counter fridge-freezer, and a separate beverage fridge. The primary bedroom includes an ensuite bathroom with Beton Ciré waxed gray walls. A guest bedroom and an additional full bath complete the main floor. Upstairs, a vaulted loft offers a lounge and media area, desk space, and a peekaboo window framing bay views. The lower level features a concrete-floored laundry room with a full-size fridge-freezer. Smart Lutron lighting and shades throughout the home add effortless modern convenience. Set on 1.5 acres moments to Mashomac, a 2600 acre preserve, the property provides a serene natural setting that enhances the home's sculptural presence. Residents enjoy access to a Boat House-exclusive to just three homes within the HOA-complete with a living area, bathrooms, outdoor shower, and dock with a dedicated boat slip accommodating up to a 28-foot powerboat. Please note: beam and draft information must be provided to ensure vessel compatibility. The community also features a deco-turf tennis court with bathroom and locker. [[Rental Registration # RP2025]] EH RR #: RP 2025 Rental Terms: July - Labor Day: $62,500

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 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.

2026 Rates: August 1-15 $20,000, September $25,000, October $20,000: 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.

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.

Located just 2 blocks from Sammy's Beach, in East Hampton, unwind at this stunning original Mid-Century home. This freshly renovated two story, three bedroom, two bath house was built with oak floors, cedar clad walls and ceiling, and antique details for a luxurious yet charming feel.It features a double height living area with floor to ceiling windows, wood burning stove, and integrated fully equipped kitchen and dining areas. Sliding glass doors lead to the expansive wraparound deck with Barbecue, dining and lounge areas, outdoor shower, and the large yard with seating and a fire-pit. The bedrooms are generously proportioned with 2 king and 1 queen beds, and upstairs there is a dedicated office and work out area with its own walkout balcony.Though quiet and elegant in nature, the home is modern where it counts. It features two large flatscreen TVs, 1 GB wi-fi and unlimited music and sound capabilities in every room. Enjoy long days on the beach, paddle board or kayak in Three Mile Harbor, or hikes through the nearby 116 acre Sammys Beach Nature preserve. Conveniently located 2 blocks from Sammys Beach, 7 minutes to East Hampton Village and only 10 minutes from Sag Harbor, the home is a true East End escape. [[Rental Registration # Pending]] Rental Terms: February: $2,975 July - Labor Day: $39,000 September: $4,500 June: $9,900 April: $2,975 March: $2,975 November: $3,200 Other / Short Term - Dec: $3,200 October: $3,200 August - Labor Day: $22,000 Memorial Day - Labor Day: $49,000 August: $18,000 January: $2,975 July: $18,000 May: $3,975

Life is Better by the Beach! Welcome to 34 Corsino Avenue, a cozy 3 bedroom, 1 bath unfurnished ranch available as a year-round rental in the desirable Miami Beach Association. Just a short stroll to the association's beautiful private beach on Long Island Sound, this charming home offers the relaxed coastal lifestyle you've been looking for. Ideally suited for one or two occupants, the home features tile flooring throughout, an updated kitchen with a new stainless steel electric range, range hood, and refrigerator, plus three bedrooms that offer flexibility for guests, a home office, or hobbies. A bright three-season room provides additional living space, while the oversized deck and private backyard create the perfect setting to relax, entertain, or enjoy the sea breeze. If you've been dreaming of year round beach living, don't miss this opportunity to enjoy one of Old Lyme's shoreline community. Pets will be considered with owner approval. Tenants will be responsible for Electric, cable/ internet and snow removal.

Academic Rental in White Sand Beach. Four Bedrooms and two full baths. Large front to back living room with wood burning fireplace. The dining room table can seat eight comfortably and the kitchen is fully applianced. The first floor laundry is just off the kitchen. There is an office/den just off the dining room leading to and outdoor patio. A short walk brings you to the beach and across the road are tennis courts, basketball court and play area.

Enjoy August in this sweet, cozy, updated home with pool. Chef's kitchen, open floorplan with 3 bedrooms, and 2 baths, this home is close to bay beaches. [[Rental Registration # 26-1149]] EH RR #: 26-1149 Rental Terms: Two Weeks: $10,000

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.

A Timeless Summer Tradition: Renovated Victorian Shingled beach house in the Borough of Fenwick Experience the quintessential New England summer in the historic Borough of Fenwick. This stunning, shingle-style Victorian beach house seamlessly blends old-world coastal charm with modern, high-end luxury. Featuring 8 spacious bedrooms and 4.5 baths, this expansive residence is the perfect sanctuary for large families or those who love to entertain against the backdrop of the Long Island Sound. The heart of the home is a totally renovated gourmet eat-in kitchen, designed for the culinary enthusiast and large-scale hosting. Beyond the kitchen, life slows down on the magnificent wrap-around screened porch-the perfect vantage point to enjoy your morning coffee or an evening cocktail while overlooking the water and catching the sea breeze. Retreat to the third floor, where a dedicated playroom offers a private escape or a quiet workspace away from the main living areas. From its cedar-shingled exterior to its thoughtfully updated interior, every inch of this home invites you to relax, recharge, and rediscover the magic of a Fenwick summer.

With direct views of the water and access to Gardiners Bay, this newly refreshed beach cottage exudes a chic and pared-down simplicity, making it the perfect waterfront retreat for relaxing days that feel like a true getaway from it all. Nestled in the serene natural surroundings of Gerard Drive in East Hampton Springs, this light-filled two-bedroom, two-bathroom cottage features central air conditioning and an abundance of outdoor activities, and the beach right on your doorstep. An outdoor shower provides a convenient way to rinse off after swimming or kayaking in the Bay or hanging out at the beach on Gerard Drive. Additionally, there's a fire pit with beach chairs on the bulkhead, offering a cozy spot to unwind at the end of a perfect day in the Hamptons. Please inquire about custom off-season dates . [[Rental Registration # RR-25-785]] EH RR #: RR-25-785 Rental Terms: August: $36,000 Other / Short Term - 11/1/2026 - 4/30/2027: $30,000 September: $20,000 October: $10,000