luxury houses with pool for rent Madison, United States

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.

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: 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.

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!

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

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.

Enjoy a beautiful airy and bright mint condition Bay Front Orient Contemporary home, perfect for relaxing and entertaining. This 4-bedroom 4.5 bath home has gourmet kitchen, fireplace, open common space for easy entertaining. First floor has access to bay side screened porch from living room and den (or 4th bedroom with full bath). Second floor master bedroom and a guest bedroom open onto upper bay side deck, a third bedroom with full bath completes the layout. Private stairs to the beach and deeded beach rights to association Bay beach just a short walk from the house. Property is close to all village amenities: Country Store, Post Office, Marinas, Bay and Sound beaches. Available Apr $10,000; May $12,000; Sept $20,000; Oct $15,000; Nov $10,000; Dec $10,000. Permit# 1020.

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!

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

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

Experience breathtaking views of Long Island Sound and Orient Point County Park from this spacious open-concept home. Beautifully updated 4-bed, 4-bath home offers private 20x40 heated saltwater pool and serene backyard. Host memorable gatherings in the spacious kitchen, perfect for indoor & outdoor dining. The expansive master suite boasts breathtaking views, king-size bed, office nook, dressing area, full bath, and private balcony. The lower level features a cozy sitting and entertainment room, an exercise room, a full bathroom, laundry facilities, a 2-car garage, and direct access to the pool and backyard. Enjoy easy access to the pristine sound beach, hiking trails, Orient State Park, and Duryeas restaurant. Located at the tip of Long Island, this exceptional home is perfect for anyone seeking coastal living with ample entertainment and relaxation space. Offered Apr $11,000; May $20,000; June $25,000; July $35,000 (RENTED); July 31-Aug14 $20,000; Aug15-Sept 8 (RENTED); Sept 10-30 $20,000; Oct $20,000; Nov $15,000. Permit# 0234.

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!

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.

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.

Beautifully renovated and furnished and now ready for its first tenants. This lovely two story home is your perfect retreat. A wonderful location close to Wades Beach, The South Ferry, and the 2,350 acre Mashomack Park and Preserve. The house sits on a 1.13 landscaped acre property complete with a heated gunite pool, pool house, outdoor shower, and spacious entertainment patio. The tranquil elegance of this home is visible everywhere, from the welcoming entry foyer to the living room and formal dining room. Enjoy the bright well appointed kitchen with access to the outdoor patio and a comfortable lounge area. Upstairs there are three guest bedrooms, a full bath and a spacious ensuite principle bedroom. This property is the newest project of Eldon Wong, a respected designer who has reinvented houses throughout the Hamptons area. His talent is showcased in this property. A great combination of comfort and high design. [[Rental Registration # 2025-L-0135]] EH RR #: 2025-L-0135 Rental Terms: June: $15,000 Memorial Day - Labor Day: $70,000 July: $25,000 August - Labor Day: $40,000

2027 Availability: June: $10,000, July: $16,000, August: $18,000, August-Labor Day: $20,000, MDW-LDW: $45,000 Off season: $4500 per month Spend your summer on the North Fork in this beautifully furnished and thoughtfully styled 3 bedroom, 3 bath Jamesport home. The home features a spacious kitchen that opens to the dining area, creating an easy flow for everyday living and entertaining. A first floor primary bedroom with ensuite bath offers added privacy and convenience, while 2 additional bedrooms upstairs share a full bath. The finished lower level provides additional space to relax and unwind. Outside enjoy quiet mornings on the covered front porch and summer days in the backyard complete with a beautiful private in-ground heated pool. Conveniently located near beaches, wineries, farm stands restaurants and all that the North Fork has to offer.

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

Experience luxury living in this newly constructed North Haven modern estate, set on 3.25 acres with breathtaking harbor views. Interior design by the renowned Melanie Roy, this estate offers a state-of-the-art chef's kitchen with a dining area overlooking the water, two stunning living rooms, and a second primary bedroom on the main level. The grand entrance is spectacular, featuring a floating staircase and an elevator. Outside, enjoy a 20x50 waterside saltwater heated gunite pool and jet spa, a spacious lounge area with magnificent views, and a path leading to the water for paddle boarding and kayaking. The property also includes a detached studio/office/yoga room with a full bath and an electric screened-in porch with panoramic waterfront views. The second level boasts four spacious ensuite bedrooms, including a grand primary suite, all with terraces and beautiful vistas. The lower level is perfect for entertainment with a large flatscreen TV, sound system, a game room with a pool table, an additional full bedroom with bath, a gym, and a 5-person sauna. With a 3-car garage and ample parking in the front courtyard, North Haven Manor also offers resident pathways to the beach and open water. Boat mooring is available, also great for kayaking and paddle boarding. Located just minutes from the village of Sag Harbor, this premier rental listing is available for THE US OPEN in JUNE, offered exclusively through Sotheby's International Realty. [[Rental Registration # R-2025-0006]] EH RR #: R-2025-0006 Rental Terms: June: $150,000 July: $375,000

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

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: July: $45,000 Other / Short Term - Dec: $15,000 October: $20,000 August - Labor Day: $60,000 August: $55,000 November: $15,000

Nestled on a quiet cul-de-sac among expansive three-acre estates, this beautifully landscaped Hamptons retreat offers the perfect blend of privacy, recreation, and convenience. Backing directly to Noyac Golf Club and surrounded by more than 135 acres of scenic hiking and jogging trails, the property is an ideal escape for summer living. Designed for effortless indoor-outdoor entertaining, the home features a dramatic double-height living room, a newly renovated kitchen, and a spacious dining room with seating for 12. A wall of sliding glass doors fills the home with natural light and opens to the expansive patio, heated gunite pool, and Har-Tru tennis court. The thoughtfully designed layout includes six bedrooms and six bathrooms, all above ground, with two en-suite guest bedrooms conveniently located on the first floor and a spacious primary suite upstairs, along with three additional guest bedrooms. Furnished with two king beds and five queen beds, the home comfortably accommodates up to 14 guests. Ideally situated just minutes from Towd Point Beach, Long Beach, marinas, and several popular waterfront restaurants, and only 12 minutes from the villages of Southampton, Bridgehampton, and Sag Harbor, this exceptional property offers easy access to the very best of the Hamptons while providing a peaceful country setting. Rental Registration #RP160829. [[Rental Registration # RP160829]] EH RR #: RP160829 Rental Terms: July: $70,000 August - Labor Day: $70,000 July - Labor Day: $140,000