luxury real estate for rent Sag Harbor, United States

Spend the summer in Sag Harbor-arguably the Hamptons' most vibrant and sought-after destination. Set on half an acre just moments from the village, this five-bedroom home is being offered as a rental for the first time, presenting a rare opportunity to experience Sag Harbor living at its best. With effortless access to the village's renowned restaurants, shops, and marinas, the home offers the ideal balance of privacy and convenience, complemented by stunning views over the bay. Designed for summer living, the open-concept main level flows seamlessly from kitchen to dining to outdoor entertaining, with multiple sets of glass doors opening to the grounds. A separate living room with fireplace provides a quiet counterpoint to the home's airy, social spaces. Upstairs, the primary suite offers a private retreat with its own deck overlooking the property and capturing beautiful water views, while additional bedrooms are thoughtfully arranged across two wings for comfort and flexibility. Outside, a heated gunite pool anchors the grounds-perfect for long afternoons, casual gatherings, and easy evenings under the stars. Ideally positioned for both relaxation and access, this is a turnkey Sag Harbor rental designed to capture the very best of the Hamptons summer. Rental Terms: Other / Short Term - 5/28/2027 - 6/30/2027: $50,000 June: $45,000

A stylish, gorgeous construction designed by award-winning architect James Merril. Set on an acre, this 5- 5-bedroom home has every desirable amenity. The primary bedroom has a terrace and a beautiful bathroom with a shower and a separate bathtub. The 4 guest rooms are all spacious and light-filled. Downstairs, there is an open living room and a den/ 5th bedroom with a full bath. An exquisite gourmet kitchen has all the bells and whistles, from a 6-burner Viking with a grill to a double Sub-Zero Fridge, wine fridge, double sinks, and dishwashers; it also has its own breakfast area. There is a formal dining area with a fireplace that is magnificent. The sunny Living Room shares the same dual-sided open fireplace. A lower-level gym. Many French doors open to the deck that has a gorgeous outdoor dining area- and a shaded lounge area with a 32' by 15' ft. heated pool. A path to the dock on the bay, which is a divine protected sanctuary, that accesses the big open bay. There is a lower basement level with a 2-car garage. The front of the house has a great veranda, all set on a quiet and charming high-end street in the Village of Sag Harbor. Rental Terms: September: $25,000 June: $60,000 November: $20,000 Memorial Day - Labor Day: $350,000 July - Labor Day: $300,000 October: $25,000 Other / Short Term - Year Round: $450,000

Situated on one of the largest lot in Sag Harbor Village at 2 builders acres, this furnished 3,000 sq. ft. Colonial offers 5 bedrooms or converted home office, 2.5 baths, outdoor shower, CAC, finished basement with play room, gym, large heated gunite pool, hot tub, all on a manicured property with organic garden, fire pit, and lovely outdoor dining. Within a short distance to the village center and its restaurants, shopping and entertainment. Store your catamaran, paddle boards and kayak at Havens Beach, or enjoy sailing at the Breakwater Yacht Club.ond largest lot in Sag Harbor Village at 2 builders acres, this furnished 3,000 sq. ft. Colonial offers 5 bedrooms or converted home office, 2.5 baths, outdoor shower, CAC, finished basement with play room, gym, large heated gunite pool, hot tub, all on a manicured property with organic garden, fire pit, and lovely outdoor dining. Within a short distance to the village center and its restaurants, shopping and entertainment. Store your catamaran, paddle boards and kayak at Havens Beach, or enjoy sailing at the Breakwater Yacht Club. Rental Terms: May: $20,000 September: $38,000

This pristine newly renovated traditional sits high on a hilltop in Wainscott, which is one of the many stunning features of this incredible rental property. Two-story, shingle style traditional home with 5,000 +/- square feet of living space offers top quality finishes throughout and offers five bedrooms, five and one-half baths, a professional kitchen with a breakfast bar, a family room, a formal dining room, a living room and two fireplaces. Sun or clouds, the entire home is filled with light enhanced by high ceilings throughout most rooms. Outdoors enjoy the new heated pool with retractable cover, a hot tub and spa, 1,800 +/- square feet of new decking and beautiful new landscaping, along with a three-car garage. [[Rental Registration # 23-1305]] EH RR #: 23-1305 Rental Terms: August - Labor Day: $115,000 July - Labor Day: $200,000 Memorial Day - Labor Day: $245,000 September: $18,000 July: $110,000 October: $18,000

Discover the perfect Fall getaway in this stunning artist's home in Sag Harbor, now available from Sept 8th - Oct 5th 2026. Ideally situated between Sag Harbor Village and Long Beach, this immaculate 4-bedroom, 3.5-bathroom residence is a true oasis, featuring a well-curated collection of art within a sophisticated monochromatic interior. Built in 2018, this contemporary farmhouse beautifully balances exceptional style and comfort. An open-plan kitchen, dining, and living area seamlessly transitions to the 32' x 16' heated gunite pool, surrounded by a bluestone patio with multiple entertaining and lounging areas. A well-thought-out setting for summer gatherings or long days by the poolside. For the art enthusiast, a well-stocked library of art and design books can be found in the first-floor lounge. On the second floor, you will find four well-appointed bedrooms, including two that feature ensuite bathrooms, as well as an additional full bathroom. To enhance your stay, the dedicated laundry room features two washers and dryers for your convenience after days at the beach. Minutes from both Long Beach and Sag Harbor Village, you can also enjoy fresh, local produce from Serene Green Farm Stand, conveniently located at the end of Parkway Drive. [[Rental Registration # RP230356]] EH RR #: RP230356 Rental Terms: October: $18,000 July: $60,000 July - Labor Day: $135,000 Other / Short Term - 12/23/2026 - 1/31/2027: $30,000 September: $12,000 August - Labor Day: $75,000

SAG HARBOR VILLAGE WOW HOUSE! This lovely 1840's Village home was recently purchased and designed to create an open floor plan with high-end details. All brand new furnishings, fantastic art, beautiful light: it has a wonderful flow for easy living. There is an outdoor deck with a new grill and a dining table. The yard is serene with chairs around a fire pit. All new systems have been installed, including Central Air, an updated kitchen with glazed Moroccan white tiles, a Viking stove and hood, and 2-inch thick marble countertops. There are two new full baths, one upstairs with a tub and one downstairs with a shower. There are 3 bedrooms upstairs, with laundry. The spacious open living area flows into a dining area that's off the enclosed kitchen. There is a separate Den/TV room with a full bath on the main floor. A deck that overlooks a newly landscaped, hedged, and fenced-in lush garden with irrigation. Featuring a Barn/Storage. There is also a full lower level of clean space. New hedges have been installed at the front of the home for privacy with a new gated-entry portico. The rear yard is serene with plantings and is seemingly quiet. There is a two-car individual parking area to the side of the house, and the yard is gated and fenced with English-style gardens. This home is move-in ready and is surrounded by the choicest homes in the Village, while the designer's taste warrants savvy appreciation. This home is minutes to the village, dining, shopping, and transportation, with the Harbor Market just around the corner for morning coffee and croissants. Here you have a quiet residence in the heart of Sag Harbor Village, with quick access to Main Street, Shopping, Dining, and Beaches. Newly listed for the first time! [[Rental Registration # R-26-0002]] EH RR #: R-26-0002 Rental Terms: September: $31,500 August - Labor Day: $50,000 August: $25,000

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

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

This Sag Harbor home offers a unique opportunity to be able to vacation in a beautifully renovated and tastefully decorated home in the middle of all the action - boating, dining, theater, shopping, swimming. This three-level home takes full advantage of the water views with a living area and wet bar on the third floor. The chef's kitchen flows seamlessly into both indoor & outdoor dining options - great for entertaining. All of the bedrooms have access to a private bathroom - two bedrooms are en-suite. The fourth bedroom is being used as a third-floor lounge area and has a pull out couch for guests. The lower level is fully finished and offers a cozy space for rainy days and functions well as a home office with natural light and walk-out access to the backyard garden. There is a full bathroom and laundry on the lower level as well. Rental Terms: August - Labor Day: $55,000 September: $40,000

Set against the exquisite backdrop of Little Peconic Bay, this unique waterfront home offers a harmonious blend of modern sophistication and waterfront beauty. With 180-degree bay views and resort-style amenities, the property is a sanctuary of elevated living. The main residence is a striking five-bedroom, four-and-a-half-bath haven, thoughtfully designed for both intimate entertaining and quiet relaxation. The great room is a striking yet welcoming space where architecture and setting work in harmony. Exposed beams and a stone fireplace ground the room with timeless style, while whitewashed ceilings and broad-plank floors keep the atmosphere open and airy. Expansive windows and sliding glass doors frame sweeping bay views, inviting the water and horizon into daily life. With sunlight streaming in by day and a cozy glow by night the space provides an ideal setting for both relaxed gatherings and peaceful retreat. The home includes a sun-drenched bay-facing breakfast table, a gourmet chef's kitchen, and a generous primary suite with a beautiful private waterfront covered deck. Four additional guest bedrooms provide accommodations for family and visitors alike. Step outside to discover a heated gunite swimming pool, a pool house, and a stunning waterfront gazebo-perfect for sunset gatherings or peaceful mornings by the shore. Located with close proximity to the Elizabeth A. Morton National Wildlife Refuge. [[Rental Registration # RP250018]] EH RR #: RP250018 Rental Terms: Two Weeks: $60,000 August - Labor Day: $120,000 Other / Short Term - 8/7/2026 - 9/7/2026: $120,000

Step into the season with a top-to-bottom Spring refresh-brand new mattresses, crisp bedding and towels, a sparkling new kitchen stove, a sizzling barbecue, and a fresh coat of paint. Watch the sunsets dance across the water and feel the cool breezes that make every evening unforgettable. With a sandy entrance to Sag Harbor Cove for a refreshing dip and an outdoor shower to rinse off, it's the perfect blend of charm and modern comfort. This gem is priced right and ready for your best summer yet-just unpack and start making memories! [[Rental Registration # RA240090]] EH RR #: RA240090 Rental Terms: September: $10,000

Welcome to 54 Bay View Drive East, Sag Harbor, where modern luxury meets waterfront living. This stunning, award-winning modern estate is a boater's paradise, boasting a deep water dock and breathtaking sunset views over Sag Harbor Cove. With 4 bedrooms, 4.5 modern baths, and 3100 square feet of sleek living space, this home offers the epitome of waterfront elegance. A primary suite on the first floor and an additional secondary primary bedroom suite on the second floor with endless water views complement this unique offering. Enjoy the convenience of a water view Chef's kitchen, multi-level decks, and a heated Gunite infinity pool. The property features geothermal heating and cooling, ensuring comfort with minimal environmental impact. Custom fixtures from Italy and an outdoor wood-burning pizza oven add distinctive charm. Located near Sag Harbor's amenities, a 10 min walk to Long Beach, and the Shelter Island Ferry, this home offers a unique summer retreat. Don't miss the opportunity to experience waterfront luxury at its finest. [[Rental Registration # 251021]] EH RR #: 251021 Rental Terms: August: $185,000 August - Labor Day: $225,000