2025 Rates: Sept $17K, October $15K**2026 Rates** May $15K, June $18K, September 8-30 $12K, October $12K. This property is a stunning waterfront home located on West Cove in the exclusive Nassau Point area. Offering breathtaking views of the Great Peconic Bay, Robins Island, and New Suffolk, this home exudes charm and sophistication.

Orient village mid century gem with pool. This newly renovated, well appointed residence is perfectly located and offers 3 bright and spacious bedrooms and 2 full baths, chefs kitchen, dining room, living room and screened in porch. The yard and pool area are fenced.

Southold Goose Creek Waterfront Home. Immaculate sun-filled home with all you will need to relax and enjoy summer. Large living room, and dining room. Well equipped Kitchen with sliders to deck, Den with amazing water views. Ensuite bedroom with water views, 2 additional bedrooms and bathrooms. Furnished deck and large yard.

Have the best getaway ever in this newly renovated home in prestigious Nassau Point! At its heart is a sunny great room with a soaring cathedral ceiling. The chef’s kitchen includes premium appliances, a large island, and flows into the living room with backyard views. The formal dining room, with bay views, is perfect for more formal gatherings.

Available July 2026 for $34,500 Available August to September 7, 2026 for $42,000 Come and enjoy the privacy that lies behind the doors of this reimagined modern ranch. Once inside you will be thrilled by the level of detail in this 2023 gut renovation. As you enter the home, you are welcomed with expansive views across the large backyard onto the surrounding vineyards.

Bright and spacious Contemporary summer rental on the North Fork. Featuring floor to ceiling windows, great room, 6 bedrooms, 3.5 bathrooms, eat-in kitchen, recreation room. Private back yard with 40x20 salt water heated pool. Offered June 1 - 28 $25,000; June 29 - July 18 $33,000; July (2 weeks) $24,000; Sept 4 - Oct 2 $30,000. Permit #1230.

Impeccable, like new ranch for rent with quality features throughout in Harbor Lights with a deeded beach and park at the end of the street.

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.

Impeccably restored 19th Century gem located in the heart of Orient Village with bay views. Close to bay and sound beaches, and a stroll to all village amenities. Featuring 2 parlors, 3 bedrooms, library, office, eat-in kitchen, updated baths, charming garden, out-door dining, and grill, out-door shower. Offered May $7,000; June $11,000; Sept $10,000; Oct $7,000; Nov $6,000. Permit #0483.

Spacious Open Floor Plan Newer Home. Inground Pool with Built in Hot Tub and Blue Stone Pool Surround. Screened Porch Overlooking Pool Area. Nice Yard. Wood Burning Fireplace. Good Wifi. Long Island Sound Beach and Historic Lighthouse Museum and Park Several Doors Away.

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).

This spectacular bluff-top home overlooking the Long Island Sound was designed for seamless indoor/outdoor living. As you enter the residence, you are instantly awestruck by the stunning floor-to-ceiling coastline views.