luxury houses with pool for rent Southold, United States

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: 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 NO LONGER AVAILABLE; 2027 RATES COMING SOON This substantial post-modern residence offers the perfect North Fork retreat for those seeking space, comfort, and effortless entertaining. From the moment you enter, the home’s expansive layout welcomes you with bright, open living areas designed for relaxing and hosting with ease. With five generously sized bedrooms and three well-appointed bathrooms, there is plenty of room to accommodate guests throughout your stay. Inside, the home features beautiful hardwood floors, detailed custom moldings, and two inviting fireplaces that create a warm and refined atmosphere. Multiple living spaces allow guests to gather comfortably or enjoy quiet moments throughout the home. Step outside and experience a truly exceptional outdoor setting designed for summer living. The backyard is centered around a heated 20' x 44' saltwater pool w/ electric cover and surrounded by multiple outdoor dining and lounging areas perfect for entertaining, relaxing, and enjoying long summer evenings. Whether hosting a casual poolside barbecue or an elegant outdoor dinner, the setting provides the perfect backdrop for memorable gatherings. This property offers the ideal combination of space, comfort, and resort-style outdoor living—perfect for enjoying the very best of the North Fork.

Entertain poolside in this stylish Mid-C Modern set on 2 acres, with views of Orient Harbor & the Sound. Handsomely furnished with master bedroom with full bath plus 2 additional bedrooms & full bath, large gourmet kitchen, den, spacious living room/dining room/common space opening to wrap-around deck overlooking pool. Walk to Village, Latham's farm stand. July 16-30 $15,000; Aug 1-15 $17,500; Aug-LD $35,000. Permit# 0321.

Stunning waterfront shingle style home overlooking Long Island Sound with private beach access. Waterview, heated pool. Wrap-around porch. Original beach stone fireplace, vintage beadboard walls, large, updated gourmet kitchen, open common area, 5 bedrooms, 3 bathrooms, large master ensuite with private screen water view balcony. Beautiful interior furnishings, with teak rocking chairs, chaise lounges and picnic table on porch and pool area for entertaining. Close to Orient Village amenities, marinas, Country store, Yacht Club, and bay beaches. Offered June 3-27 $28,000; Sept 2-16 $14,000. Permit# 1108.

This exceptional residence is ideally situated near to Shinnecock Bay and only moments from the ocean. Enter through a welcoming foyer into a light-filled, open-concept living space featuring a fireplace and a striking custom paneled ceiling. The thoughtfully designed eat-in kitchen is fully equipped and seamlessly connected to the dining area, creating an inviting setting for both everyday living and entertaining. The first floor offers a well-appointed primary suite with private bath, an additional guest bedroom, a full bathroom, a cozy library or sitting nook, a laundry room, and a powder room. Throughout the home, exquisite marquetry craftsmanship, stained glass windows and panels, and curated artwork highlight the home’s unique character and attention to detail. Upstairs, the second level provides two additional guest bedrooms and a full bathroom. A covered walkway connects the main house to an impressive 20’ x 50’ indoor, ozone-treated swimming pool, complete with a full bath and sauna—perfect for relaxing on rainy days or unwinding after a day at the beach. Outdoors, a private inner courtyard patio with pergola offers multiple spaces for al fresco dining and lounging, along with a barbecue area ideal for hosting family and friends. The fully finished lower level adds even more versatility, featuring a full gym and dedicated Pilates room. The private backyard setting invites evenings gathered around the fire pit after days spent by the bay or ocean. The home also includes bikes, kayaks, and a small boat, making it an ideal retreat for outdoor and water-sport enthusiasts. All of this is just a short drive to the shops, restaurants, and entertainment of Hampton Bays and Southampton. Available for summer and even a potential US Open stay. MD-LD: $85,000, July-LD: $65,000, Aug-LD: $35,000, Short Term: $20,000.

Discover the charm of Amagansett at this stunning Bluff Road Beach House, available for summer and fall 2025. Located in one of the area’s most sought-after spots, this historic 5+ bedroom home offers spectacular views of the dunes and ocean, with a perfect mix of vintage character and modern comfort. Built in 1911 and recently renovated, the home features a sun-soaked interior, full of natural light and cozy charm. Whether you're lounging in the spacious living areas, enjoying a morning coffee on the front porch, or entertaining in the expansive backyard, this property is designed for ultimate relaxation and enjoyment. The home boasts: 5+ spacious bedrooms, ideal for family or guest stays, a newly furnished, open and inviting floor plan, a large backyard with a private pool, perfect for lounging and summer fun Proximity to shopping, dining, beaches, and transportation (no car needed!) Whether you're looking to unwind with a peaceful ocean breeze, entertain in style, or take in the surrounding beauty, this Bluff Road Beach House offers the perfect setting for a memorable vacation. Book your stay for 2025 and experience the best of Amagansett living! [[Rental Registration # 22-905]] EH RR #: 22-905 Rental Terms: Winter Season: $90,000 Per Month