luxury houses with terrace for rent Southold, United States

Summer is here, and this home has vacation written all over it. Enjoy spectacular sunset water views of the Long Island Sound from the spacious wrap-around deck or from the bright, open-concept living spaces inside. Perfect for entertaining, the layout features 4 bedrooms and 2 full bathrooms, offering a beautiful oasis for relaxation and togetherness. The lifestyle here is effortless: Kenny's Beach access is just steps away (.02 miles) for swimming in the Sound, complemented by a refreshing outdoor shower back at the house. Plus, you can leave the car behind and stroll down the road (.03 miles) to grab lunch or dinner at the hot new local restaurant, Little Fish. Let's get you set up in the perfect summer getaway—inquire today! Availability: June 15-June 30th $10K | July $35K | August $30K

2026 Rates: September $7500; October $10,000: Discover your perfect getaway in this expansive and meticulously updated ranch home, designed for relaxation and rejuvenation. Experience a resort-like atmosphere with the stunning gunite, heated saltwater pool, complemented by a beautiful stone surround and convenient outdoor shower. Step inside to find high vaulted ceilings that create an airy ambiance and an abundance of natural light. The home boasts stunning hardwood floors and is elegantly appointed with multiple living areas that provide the perfect balance of open space and private retreats. Ideally situated within walking distance of Kenney’s Beach, you’ll find yourself just moments away from charming local cafes, unique boutiques, renowned wineries, and exceptional dining options. This North Fork gem is truly the ultimate summer haven. Don’t miss your chance to experience the perfect blend of comfort and convenience!

Offered June $10,000 ($2,500/wk); July $20,000 ($5,000/wk); Aug $25,000 ($6,250/wk); Sept $12,000 ($3,000/wk); Oct $10,000 ($2,500/wk). Two-week minimum. 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.

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!

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

Enjoy a relaxing North Fork Summer at 875 Deefoot Path, a beautifully appointed four bedroom, four bath home conveniently located near Nassau Point Causeway Beach. The home features 2 primary ensuites, one located on the first floor. The spacious layout offers comfort, privacy and an ideal setting for a summer getaway. Spend your days at the beach, wineries, restaurants and return home to unwind and enjoy all this property has to offer. Summer 2027 rates: June $10,000, July $17,500, August $19,500, August-LDW $22,500, MDW-LDW $49,500 Off season pricing and available upon request.

Sunny, bright, and tastefully furnished, this designer’s Victorian offers five bedrooms and two updated full baths, with a seamless flow between the main living spaces. The professionally landscaped front and rear gardens include a heated saltwater pool, dining and barbecue patios at both the front and poolside, three hammocks, and an outdoor shower. Nassau Point Beach is at the end of the road, and a marina is nearby. Every detail has been considered to make relaxing and entertaining easy. Offered for August 2027 for $40,000. Permit #1501.

Privately elevated at the end of a long driveway sits a stunning modern home, Clearhouse. With timeless architectural planning by SP design the home is dramatically raised on a central plinth and cantilevers horizontally with floor to ceiling windows and sliding glass doors to create the ultimate indoor/ outdoor modern luxury living. Clearhouse offers one of the single greatest vistas on the east end of Long Island. The house has 360-degree views - 180 degrees being Peconic Bay, The North Fork, The Long Island Sound, and Connecticut - the south view is indigenous manicured forest with undulating elevations. On the first floor you will enjoy a full-width travertine terrace and private office. The upper floor is equipped with a gourmet kitchen with signature appliances, dining area with a wall of glass that opens to let the outdoors in, sitting area and large primary bedroom with views from every angle. The primary bedroom is comprised of 3 sides of glass - the width of the room opens completely to the elements like a modern treehouse. The lower guest level, with equally incredible vast views has a perfectly positioned media den and 2 ensuite guest bedrooms with sweeping bay views. The rooms reveal themselves in a horizontal band with architectural floor to ceiling windows. The interior synthesis of stone and dark rosewood reclaimed from a Manhattan bank and leather details create a warmth and glow that envelop the senses. A level of luxury permeates. Eye catching details such as a suspended black fireplace and world class art and furniture create a dreamy ambience. The home offers a dock with a 6,800 lb. boat lift, including additional room for a 55' boat and a 30' boat. Unparalleled sunset views every evening and ever changing light throughout the day. EH RR #: 2024-L-0045 Rental Terms: June/July: $110,000 Memorial Day - Labor Day: $200,000 July: $85,000 August: $85,000 July - Labor Day: $175,000 August - Labor Day: $105,000

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: 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: 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!

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.

Modern design meets coastal enchantment. A beautiful waterfront retreat, built partially over the water in the coveted Shelter Island Heights enclave. This modern boathouse-style home, c.1920, offers 3 beautifully spaced bedrooms, including one with a mesmerizing glass-bottom floor revealing the harbor below, and 3 bathrooms. Meticulously renovated by its designer-owner, the home exudes a refined nautical spirit with soaring ceilings, natural textures, and panoramic water views create a sense of calm and inspiration throughout. Outdoor living features two decks, including one with a cedar hot tub overlooking Dering Harbor. Additional highlights include a sauna, outdoor shower, and a vintage Airstream trailer. A floating dock accommodates boats (30" depth at low tide). Residents enjoy access to community tennis courts and a private beach club, with nearby golf, beaches, nature preserves, trails, shops, restaurants, markets, and hotels. The Shelter Island Yacht Club is close by, and convenient transportation-including boat rentals, the North Ferry, Jitney, and train-makes travel between NYC and the North and South Forks effortless. High-end appliances, fine linens, bicycles, and beach essentials are provided for a seamless, elevated stay. A wonderfully inspired waterfront haven-modern, magical, and truly unique. [[Rental Registration # #L-0009]] EH RR #: # L-0009 Rental Terms: July: $70,000 September: $70,000

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.

Refreshed log cabin on a large and private piece of property abutting a reserve. This rental is close to Greenport village, and also all the amazing vineyards and farm stands that the north fork is known for. This great house has three bedrooms, and two baths, foosball, air hockey, an outdoor hot tub, and brand new pool in 2025. Updated kitchen and baths, ready for enjoyment. [[Rental Registration # 0952]] EH RR #: 0952 Rental Terms: Winter Season: $35,000 Per Month July: $27,000 September: $22,000 August - Labor Day: $27,000 June: $22,000 Other / Short Term - Year Round: $70,000 May: $20,000 October: $20,000

Stunning new modern home with an abundance of natural light throughout. 4 bedroom, 3 bath home with plenty of room for your loved ones. Home has a large open living space with oak floors and high ceilings with huge Anderson doors that opens onto extensive covered deck for seamless indoor outdoor entertaining. Two guest bedrooms and a bathroom complete the first floor. The master suite is on the second floor with a balcony to enjoy morning coffee, a walk through closet, and bathroom with free-standing soaking tub and large shower. The lower level has with sealed concrete floors with underfloor heating, a spacious living/ den area, office space, bedroom, bathroom and laundry room and separate entrance. Great yard with mature Japanese maple tree, birches and hedging. Please call with any questions or to set up an appointment to view. [[Rental Registration # 2025-L-0061]] EH RR #: 2025 -L-0061 Rental Terms: August - Labor Day: $30,000 Memorial Day - Labor Day: $62,500 August: $22,500 July - Labor Day: $47,500 July: $22,500

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.

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.

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.

New Kitchen Renovation!! Modern waterfront residence with expansive yard and private dock near Long Beach. Enjoy long summer days sailing, kayaking, swimming or swinging in the yard and followed by family bbqs. Great location with proximity to Sag Harbor village restaurants and shops and private outdoor oasis. Revel in spectacular sunset views from the wrap around deck with comfortable seating that is also perfect for outdoor dining and entertaining. Rental Reg. # RP201766 - Reg. Expires 6/07/2023 EH RR #: RP201766 Rental Terms: Other / Short Term - Year Round: $375,000

Available for rent, this newly renovated Sag Harbor estate blends modern sophistication with laid-back coastal charm-perfect for a luxurious Hamptons escape. Fully gut-renovated and thoughtfully expanded, the 2,680 sq. ft. home features brand-new hardwood oak floors, Restoration Hardware finishes, a built-in sound system, and an abundance of natural light. The main living room boasts soaring ceilings, a custom bar, and seamless flow into the open-concept kitchen outfitted with top-of-the-line WOLF, Sub-Zero, and Miele appliances. With five bedrooms and four-and-a-half spa-like baths, the home comfortably accommodates guests, including two separate master suites with ensuite baths, soaking tubs, and walk-in showers. A flexible nursery space can serve as an office or dressing room, and a second private office at the entrance is ideal for remote work. Outside, enjoy a south-facing 0.58-acre property with a heated gunite pool, sun-drenched deck, lounge and dining areas, and lush landscaping. The home also includes solar panels, an electric car charger, a full laundry room, and deeded beach rights-perfect for launching kayaks or paddleboards. Just a mile from Long Beach and moments from Morton Wildlife Refuge and Noyac Golf Course, this rental offers the ultimate in Hamptons living. [[Rental Registration # RP251335]] EH RR #: RP251335 Rental Terms: September: $35,000 October: $20,000 November: $15,000 Two Weeks: $17,000 Other / Short Term - Dec: $15,000

Convenient to town and bay beaches, this recently renovated home is picture perfect. Features 3 bedrooms, 2 baths, living area, current kitchen, and a crisp decor. Outside entertaining under a pergola. A great Hampton's vacation home. Available year round for $110,000. [[Rental Registration # Rp250475]] EH RR #: Rp250475 Rental Terms: Other / Short Term - Year Round: $115,000 July: $30,000 August - Labor Day: $35,000 June/July: $45,000 Memorial Day - Labor Day: $75,000 July - Labor Day: $65,000 June: $15,000

Escape to the heart of the North Fork in this beautiful, spacious four-bedroom home, perfectly designed for entertaining and hosting. Inside, you'll find ample living space complemented by a fully finished basement—ideal for extra lounging or movie nights—while the private backyard oasis features a sparkling heated pool for endless summer fun. Centrally located just one mile from Breakwater Beach, this home offers unbeatable access to the very best of the region, putting you just minutes away from the charming shops on Love Lane, premier local vineyards, and acclaimed farm-to-table restaurants. Book your stay today and secure the perfect central base for your ultimate retreat!

Fabulous, like new modern home available for rent. Serene water views from living areas, deck and gunite, in-ground, heated swimming pool. A short 300' to the sandy bay beach. The home was completely renovated in 2020. The home offers open concept living at its best with wall to ceiling glass doors letting the outdoors in and offering serene water views. The first floor also offers a separate den that can also be used for an additional bedroom. There is a guest bedroom with full bath on the first floor. The second floor has 2 additional en-suite bedrooms (including the large primary suite with a sumptuous bathroom) and a sun filled landing designed for relaxing and play. This home is a perfect vacation home offering all modern amenities, a swimming pool, water views with access to a sandy bay beach. [[Rental Registration # RP220388]] EH RR #: RP220388 Rental Terms: July: $59,000 March: $10,000 June: $29,000 Memorial Day - Labor Day: $129,000 January: $10,000 September: $20,000 May: $12,000 February: $10,000 October: $15,000 August - Labor Day: $65,000 July - Labor Day: $115,000 November: $15,000 August: $59,000 April: $12,000 Winter Season: $50,000 Per Month Other / Short Term - Dec: $15,000