luxury houses with pool for rent Sag Harbor, United States

A private oasis in the heart of Sag Harbor. Located on a beautifully landscaped shy acre in the heart of Sag Harbor's historic district, this Federal-style house dates back to 1780 and has been beautifully restored and updated with every modern amenity. Featured in Elle Décor and The New York Times, this peaceful and private retreat, only a short stroll from Sag Harbor's wonderful shops and restaurants, boasts century old boxwoods, an allée of cherry trees, a gunite pool, bluestone terraces, a Carriage House reimagined as a pool house, and even a Chicken Coop. The principal rooms include a library, living room, mudroom, double height great hall perfect for entertaining, a TV room and office, dining room overlooking the garden and a gourmet chef's kitchen with cathedral ceiling, 2 Bosch dishwashers, a Viking range, a SubZero refrigerator, wine cooler and fireplace. The private rooms include an exquisite primary suite with fireplace, cathedral ceiling and spa bathroom, two en-suite guest bedrooms, staff quarters with separate egress, as well as two additional private guest areas each featuring an en-suite bedroom with living room for a total of six bedrooms, six fireplaces and seven bathrooms. Beautifully designed for gracious living and entertaining, this property is truly the jewel of Sag Harbor. Rental Terms: Other / Short Term - Extended Season: $145,000

Also Available May 24 - Jul 31 $235K, Sep 4 - Nov 30 $160K Historic Sag Harbor, brilliantly renovated, offers sophisticated, relaxed stylish living. The 1750 Main house offers delightful, light, entertaining public spaces, luxurious en-suite bedrooms and staff quarters. The Carriage house offers added entertaining space with rare architectural features. This rare, near acre, village compound includes an oversized gunite pool, stone terracing, gracious garden dining and entertaining surrounded by a classic garden featuring historic box hedges, cherry trees and wonderful privacy. Rental Terms: Memorial Day - Labor Day: $425,000 July - Labor Day: $335,000 July: $140,000 August - Labor Day: $195,000 Other / Short Term - May 24 - Jun 30: $95,000

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

In the Village of Sag Harbor, with a large veranda and a summer porch, a heated gunite saltwater pool with Jacuzzi, surrounded by a private garden, comfy lounge chairs, outdoor dining with Umbrellas and double Barbecue grill, and an entertaining barn to hang out and play ping pong in. Inside the furnishings are magazine wonderful. There is an open dining room that flows into a living room with an overstuffed white couch and chairs, which opens into a den/TV room/ library with a fireplace. Light-filled and spacious, the brand-new country kitchen is a great hangout, featuring a Sub-Zero Fridge, a Viking Stove, a farm sink, a pantry, and a new washer and dryer. The new oversized Primary Bedroom addition is gorgeous, featuring a new bath with a separate tub, shower, and double sinks. There is an extra full bath downstairs with a tub. Upstairs are 3 spacious bedrooms and another full bath. Central AC, this house has all the perks and tons of charm. The gardens have exploding flowers, a lush green yard, old-world trees, and a fenced saltwater heated pool. On a quiet street, but close to everything, parks, Main St., dining, and bay beaches. Featured in design publications, this is the perfect essential retreat. Comes with bikes too. Please feel free to contact me for a video tour. Rental Permit R-25-0058 expires 06/14/2027 Rental Terms: August - Labor Day: $58,000 August: $55,000

Beautiful Bucolic Waterfront -- Best Sunsets in the Hamptons. Overlooking Noyak Bay, this newly constructed, triple-mint, modern manor boasts breathtaking water views and stunning sunsets. The soaring floor to ceiling windows, expansive decking, heated gunite waterside pool, plush outdoor furniture, cozy fire pit, outdoor shower and Lynx professional grill, adorn the water side veranda, creating a grand and sumptuous Hamptons experience. So, too, this property has a rare and coveted private deep water dock for backyard paddle boarding, kayaking or...bring your own boat. Ideal for entertaining, this home is appointed with an Il Forno pizza oven, sous vide technology, an outdoor herb garden and an enviable array of Japanese chef's knives, surely to fascinate the boldest of home chef's. With rich oak, warm walnut and modern steel finishes this property exudes serenity and grace and is sure to impress. Impeccably decorated and beautifully appointed, this modern retreat is mired among majestic marine sea grasses which, like a metronome, sway in time to the warm coastal breezes. Conveniently located in the up and coming beach community of Pine Neck. Minutes from ocean beaches, a stone's throw from historic downtown Sag Harbor and a short drive from Bridgehampton, this 5200 square foot, 5 bed room, 6 bath jewel is not to be missed. [[Rental Registration # RP220659]] EH RR #: RP220659 Rental Terms: Two Weeks: $140,000 August: $250,000 August - Labor Day: $275,000 Other / Short Term - Weekly: $70,000 Memorial Day - Labor Day: $550,000 July: $250,000

Also available: July $40k, Aug $45k, Sept $12k Beautifully renovated 4 bedroom, 3.5 bath contemporary with bay views from second floor living room. Open floor plan, with professional kitchen, marble counter tops, and stainless steel appliances. Additional office space with futon. Bathrooms are also all recently renovated. Short distance to Long Beach and minutes from Sag Harbor Village. RP # 200736 exp. 6/18/24 EH RR #: rp241233 Rental Terms: August - Labor Day: $50,000 May: $10,000 July: $45,000 Memorial Day - Labor Day: $110,000 Winter Season: $30,000 Per Month Other / Short Term - Year Round: $145,000 June: $20,000

Also Available Dec 2024 for $13,000 Newly upgraded for summer 2024, this offering has its own dock with potential kayak and paddleboard, and is 0.4 miles to Long Beach, a gorgeous 1+ mile stretch of West Facing beach. The chic home is west-facing for sunsets from almost every room--even the walk-out lower level. Brand new Ipe decking, modern wire rails, Gunite pool and deep-water dock make for an amazing waterfront experience. There is a tremendous outdoor entertaining space on two levels. The 4,500+/- sq. ft. home is spacious with open flow. A New two-story living room setup features an stunning Modern window package and brand new furniture, plus a big new TV! The kitchen and dining room also offer walls of windows that drench the home with light and views. This is the perfect house for entertaining with 5 bedrooms (plus a room with a sofa bed), and 5.5 baths. A finished lower level offers a wet bar, pool table, family room and pool bath, with a wall of windows and views out to Long Beach. New spacious Ipe decks with cable rails allow for easy outdoor living and entertaining just above the water. The house is in a quiet neighborhood, 2 minutes to Sag Harbor Village. When all the backyards lose their foliage at other Hamptons properties, this winter rental has its most gorgeous views--open water views from all 3 levels. [[Rental Registration # RP200192]] EH RR #: RP200192 Rental Terms: October: $15,000 April: $10,000 February: $8,000 May: $10,000 September: $30,000 January: $8,000 March: $8,000 November: $10,000 Other / Short Term - Dec: $10,000 August - Labor Day: $87,500 August: $85,000

Very stylish, renovated beach-style residence in Bay Point, with water views from almost every window and outdoor decking, offers four bedrooms, three baths, and a new heated salt-water pool. The open floor plan main level includes a new gourmet-style dine-in kitchen, open dining, and living room with fireplace that opens onto a deck. The master suite includes a luxurious new bath and its own deck. An additional guest bed/den and laundry are located on this main level also. The finished at-grade level with its own living room and kitchenette includes two guest bedrooms, and a spa-bath. An outdoor shower and fire pit join the pool in the private backyard. The attached one-car garage adjoins a covered car port. Mooring rights now available. [[Rental Registration # RP250380]] EH RR #: RP250380 Rental Terms: Other / Short Term - Year Round: $180,000

Discover refined Hamptons living in this beautifully designer-finished Sag Harbor Village retreat, just moments from shops, dining, and the waterfront. This 5-bedroom, 4.5-bath home features an open, light-filled layout where a sophisticated living and dining area flows effortlessly into a well-appointed kitchen with a large center island and counter seating, perfect for casual entertaining. Two ensuite bedrooms are conveniently located on the first floor, ideal for guests, while the second level hosts three additional bedrooms, including a spacious primary suite with a private deck overlooking the serene backyard. The finished lower level adds versatile space with a media and entertainment area, as well as a dedicated home office. Outdoors, enjoy a private oasis with a heated gunite pool, a stylish cabana with lounge seating and television, and a separate dining area for eight-perfect for effortless summer entertaining. With its prime village location, elevated designer style, this Sag Harbor home is an ideal Hamptons getaway-offering both tranquility and access to all the excitement of Sag Harbor Village. Rental Terms: Other / Short Term - 8/24/2026 - 9/7/2026: $50,000 June: $50,000

Moments from the heart of Sag Harbor Village, this exceptional designer residence offers a rare opportunity to experience a seamless blend of modern sophistication and timeless coastal living. Privately sited on a beautifully landscaped 0.47± acre, the property delivers a serene and elevated summer retreat in one of the Hamptons' most desirable locations. Spanning approximately 4,500± square feet, the home is thoughtfully designed with expansive, light-filled interiors and an effortless flow throughout. The main level features a gracious open-concept layout, anchored by a beautifully appointed chef's kitchen with premium appliances and custom finishes. Adjacent living and dining spaces are designed for both relaxed living and refined entertaining, complemented by a separate lounge with fireplace that provides an intimate setting for quieter moments. The second level is highlighted by a well-proportioned primary suite offering a private sitting area and spa-inspired bath, creating a true retreat within the home. Additional guest bedrooms are generously sized and finished with the same attention to detail, offering comfort and flexibility for a variety of living arrangements. The outdoor setting is equally compelling, with meticulously maintained grounds that create a sense of privacy and calm. A heated pool is surrounded by expansive lounging and entertaining areas, ideal for enjoying the full Hamptons lifestyle-from sun-filled afternoons to evening gatherings under the stars. A fully finished lower level enhances the offering, providing additional space for recreation, media, or wellness use-thoughtfully designed to support both relaxation and entertainment. Ideally located just minutes from Sag Harbor Village, the property offers convenient access to renowned dining, boutique shopping, marinas, and local beaches, while maintaining a peaceful residential setting. An exceptional rental offering defined by design, comfort, and location-crafted for a sophisticated Hamptons summer experience. Rental Terms: May: $35,000 June: $40,000 Other / Short Term - Year Round: $265,000 August: $87,500 September: $30,000 July: $85,000

No expense was spared on this Brand-New, 10,000+/- sq. ft. gated, Custom Construction. Available for the first time for June/July, 2024. This is perhaps the nicest estate rental offering available just outside Sag Harbor Village, only a 1/2 mile to Long Beach. The home itself is magnificent, custom designed, with no detail overlooked. It has every amenity--7 ensuite bedrooms, elevator, magnificent custom-designed Kitchen, glass Breakfast Room, oversized Great Room and Living Room with Wet-bar. The first floor also features a luxurious Bar Room/Butler's Pantry and a large 1st-floor Office with TV. The lower level offers a Gym, Game Room, and Hotel-like Spa, with Steam Shower, Soaking Tub, Shower, and Sauna. The majestic property offers 1.5+/- acres of full lawn--gated and fully enclosed. It includes a Pickleball Court, Basketball, 45' Pool, Hot Tub, Outdoor Living Room, and Outdoor Kitchen/Bar. The property is perfect for family outdoor living and entertaining. And for local daily activities, the offering is also only moments to Community Tennis, two gorgeous Beaches, Sag Harbor Marinas and the Shelter Island Ferry. Rental Terms: November: $30,000 Other / Short Term - Year Round: $650,000 Winter Season: $135,000 Per Month

Exquisite New Construction | 6 Bedrooms | 6.5 Bathrooms | 5,500+ Sq. Ft. | Resort-Style Amenities Nestled on meticulously landscaped grounds in a prime Hamptons location, this stunning, newly constructed residence offers the perfect blend of contemporary elegance and effortless indoor-outdoor living. Spanning three luminous levels, the home is just moments from pristine beaches, Sag Harbor's charming Main Street, and the vibrant energy of Bridgehampton-making it an idyllic retreat for both relaxation and entertaining. Grand & Light-Filled Living Spaces A soaring entryway bathed in natural light welcomes you into an expansive open-concept layout, where sleek modern design meets unparalleled functionality. The chef's dream kitchen boasts dual oversized islands, premium appliances, and a seamless flow into the dining and living areas, anchored by a cozy fireplace. Floor-to-ceiling sliding glass doors blur the lines between indoors and out, opening to a sprawling deck designed for alfresco dining, sunset grilling, and tranquil lounging-all overlooking the lush, private grounds. The main level also features a sun-drenched den with high ceilings, a full bath, and a chic powder room, offering flexibility for guests or a home office. Luxurious Upper-Level Retreat Ascend to the second floor, where four generously sized en-suite bedrooms provide serene sanctuaries for family and guests. The primary suite is a true haven, complete with a private balcony and a spa-inspired bathroom featuring designer finishes. An additional office/media room and a spacious laundry room add convenience to this level. Entertainer's Paradise - Lower Level & Outdoor Oasis The fully finished lower level is an entertainer's delight, featuring two additional bedrooms, a family room with a kitchenette, a full bath, and a second laundry area-ideal for guests or extended stays. A state-of-the-art home theater promises cinematic nights in. Sliding glass doors from every room lead directly to the resort-style backyard. Outside, paradise awaits: - 20x40 heated gunite pool surrounded by expansive lounge areas - Professional-grade pickleball court for friendly competition - Covered outdoor kitchen & dining pavilion for gourmet grilling and gatherings - Cedar-enclosed outdoor shower & dressing room for post-beach or poolside refreshment Premier Amenities & Sustainable Living Additional highlights include a two-car garage and solar power integration, blending modern convenience with eco-conscious living. A Rare Hamptons Gem Designed for those who seek both luxury and livability, this home effortlessly balances sophistication with comfort. Whether as a year-round residence or a seasonal escape, 130 Highview is a must-see property that defines Hamptons living at its finest. Schedule your private tour today-this is one you won't want to miss." [[Rental Registration # RP261343]] EH RR #: RP261343 Rental Terms: March: $20,000 October: $25,000 Other / Short Term - Dec: $20,000 Memorial Day - Labor Day: $300,000 February: $20,000 May: $45,000 June: $60,000 November: $20,000 April: $20,000 January: $20,000

An architecturally distinguished modern barn, this three-bedroom residence offers a rare fusion of artistic design, refined finishes, and resort-level privacy. Set behind meticulously curated landscaping, the home presents a sculptural silhouette and interiors defined by soaring volume, gallery-like light, and a sophisticated contemporary palette. The main living spaces flow effortlessly to the outdoors, framing views of the property's lush grounds. A fully finished loft-ideal as a private office, studio, or additional lounge-elevates the home's versatility and provides a serene, sunlit retreat separate from the primary living areas. The backyard functions as a private resort, anchored by a pristine pool surrounded by native plantings that create a sense of seclusion and seasonal beauty. The outdoor living and dining areas offer elegant settings for both intimate relaxation and open-air entertainment. Perfectly positioned between Sag Harbor and East Hampton Village, the property allows equal access to luxury boutiques, acclaimed dining, marinas, and the Hamptons' most coveted ocean beaches. This is modern East End living at its most polished-where architectural artistry, privacy, and premier location converge. [[Rental Registration # 24-1449]] EH RR #: 24-1449 Rental Terms: October: $30,000 Two Weeks: $15,000

Available, year-round! Flex start date of Sept 15,2026 or Oct 1, 2026. Nestled in the hamlet of North Haven, just minutes from the heart of Sag Harbor Village, this exceptional Hamptons retreat embodies refined luxury and timeless design. Thoughtfully crafted with bespoke finishes throughout, the residence offers four bedrooms and five baths, including two first-floor ensuite guest rooms. The elegant interior features a chef's kitchen with generous dining space, a dramatic great room and four tranquil bedrooms (all en-suite) designed for comfort and privacy. Outdoors, an expansive bluestone terrace provides the perfect setting for entertaining, overlooking a serene gunite pool surrounded by beautifully curated gardens. A sweeping circular driveway and lush landscaping create a sense of seclusion, while the property's prime location places you moments from Sag Harbor's renowned beaches, acclaimed restaurants, and charming boutiques. [[Rental Registration # RP#R-2024-0011]] EH RR #: RP# R-2024-0011 Rental Terms: Other / Short Term - Year Round: $215,000

Down a long drive, this charming Hamptons classic house is situated on a professionally landscaped acre. Tucked away in a quiet community and only a stone's throw to both Bridgehampton and Sag Harbor villages. This stylish professionally decorated home is fully equipped with 4 bedrooms and 2.5 bathrooms. The first floor boasts a sun-drenched great room with designer furniture and lighting, wide plank floors and a brick fireplace. Additionally, there is a master bedroom with an en suite bathroom. The kitchen is beautifully appointed with a top of the line Lacanche oven, there is also a powder-room, large pantry, laundry and mudroom with access to the pool and back garden. The second floor has three additional guest bedrooms with beautiful views of the grounds, one of the bedrooms has a walk-in closet and on the second floor there is an oversized shared bathroom. Ideal for summer entertaining the back and front gardens offers complete privacy with an expansive wrap around deck, a heated pool, outdoor shower, and a generous fenced in yard. A true gem not to be missed! #RP201221 Exp 2/10/2025 [[Rental Registration # RP250191]] EH RR #: RP250191 Rental Terms: Two Weeks: $20,000 July: $40,000 July - Labor Day: $85,000 August - Labor Day: $50,000