Mid Century Contemporary Home Rental Long Island Sound Views
$ 8000
1620, Aquaview Avenue, Town of Southold, New York
5 rooms
1800 sq ft
Mid-Century Contemporary home with Long Island Sound views. Features cathedral ceilings, large windows, water view deck, 1000 sq ft living area, 800 sq ft finished basement with recreation room, office, renovated bathroom, and laundry. Perfect for those seeking a bright, open, and relaxing space with water access.
Orient Village Arts & Crafts Home Rental
$ 9000
1125, Navy Street, Town of Southold, New York
5 rooms
2400 sq ft
Beautifully updated Arts & Crafts home in Orient Village, one block from the harbor. Features a gourmet kitchen, enclosed porch, fenced yard, outdoor shower, and deck. Perfect for those seeking a charming and convenient rental.
Home for Rent
$ 35000
495, Maple Lane, Town of Southold, New York
5 rooms
1600 sq ft
Rental Registration #: 0321 Entertain poolside in this stylish Mid-C Modern set on 2 acres, with views of Orient Harbor & the Sound. Handsomely furnished...
2 Bedroom Ranch Home Rental Breakwater Beach Summer 2025
$ 8000
1600, Captain Kidd Drive, Town of Southold, New York
3 rooms
1000 sq ft
Sweet Ranch Style Home in Breakwater Beach Community. 2 bedrooms, 1 bath, sleeps 5. Open concept, cathedral kitchen, south-facing. Wood floors, central air, laundry, deck, BBQ, spacious yard. Available summer 2025.
Mattituck Cozy House For Rent 3BR 2BA
$ 3800
705, Maple Lane, Town of Southold, New York
5 rooms
1800 sq ft
Cozy 3-bedroom, 2-bath house on 1+ acre in Mattituck. Features hardwood floors, renovated bathroom, fireplace, balcony, AC, full basement, garage, and is close to beaches, schools, and shops. No brokers.
Greenport Waterfront Cottage Rental 3 BR 2 BA
$ 15000
165, Sterling Street, Town of Southold, New York
5 rooms
1700 sq ft
Charming 3 BR, 2 BA cottage in Greenport's historic district, a block from the Maritime Village. Enjoy waterview deck, close to beaches & wineries. Perfect for those seeking a peaceful yet central location.
Vacation Home Rental near Beach with Pool and Sports Court
$ 16500
2300, Pine Tree Road, Town of Southold, New York
6 rooms
3000 sq ft
Fully fenced home with heated saltwater pool, multiple outdoor dining areas, basketball and pickleball court, firepit, playroom, updated kitchen, main bedroom with water views, kayaks, paddleboards and beach gear. Perfect for families seeking a relaxing vacation rental near the beach. Two week minimum rental.
Southold Horse Farm Estate: 5BR, 3.5BA, Heated Pool, Family Retreat
$ 35000
425, Jacobs Lane, Town of Southold, New York
8 rooms
Contemporary horse farm estate in Southold, perfect for families and friends. 5 bedrooms, 3.5 bathrooms, heated pool, fire pit, and expansive deck. Close to beaches and town amenities.
Furnished 3 Bedroom Home Rental Jan-Apr & Jul-Aug
$ 3950
3670, Rocky Point Road, Town of Southold, New York
5 rooms
3800 sq ft
Beautifully renovated 3 bedroom, 2 bathroom home. One floor living with deck and yard. Fully furnished. Available Jan 2025-Apr 2025 and Jul 1-Aug 15. Not a year-round rental.
Modern Farmhouse w Pool near Beach
$ 20000
950, Tasker Lane, Town of Southold, New York
7 rooms
3500 sq ft
Newly constructed modern farmhouse in Stirling Eastern Shores with private beach access. Features chef's kitchen, Great Room with fireplace, 3+ bedrooms, 2.5 bathrooms, 2-car garage, heated saltwater pool, and outdoor shower. Ideal for summer living.
Bay Front Contemporary Home Rental
$ 5000
1390, Willow Terrace Lane, Town of Southold, New York
8 rooms
28000 sq ft
Beautiful Bay Front home, perfect for relaxing and entertaining. Features 4 bedrooms, 4.5 baths, gourmet kitchen, fireplace, screened porch, and private beach access. Close to village amenities.
Spacious Apartment with Modern Kitchen and Renovated Bathroom
Town of Southold, New York
Spacious apartment with modern kitchen, renovated bathroom, and ample closet space. Hardwood floors throughout. Suitable for those seeking a convenient location and value.
Nassau Point Summer Rental Newly Renovated Home Pool Hot Tub
$ 38000
5270, Nassau Point Road, Town of Southold, New York
9 rooms
3500 sq ft
Newly renovated home in prestigious Nassau Point, perfect for a summer getaway. Features a chef's kitchen, multiple bedrooms, heated pool, hot tub, and outdoor fireplace. Ideal for families or large groups. Available July 7th - August 10th.
Cutchogue Summer Rental 4BR 3.5BA Pool Beach Access
$ 30000
250, Pine Tree Court, Town of Southold, New York
7 rooms
2800 sq ft
Summer rental in Cutchogue! This stunning home features 4 bedrooms, 3.5 baths, an in-ground pool, wrap-around porch, 2 living rooms, and open-concept kitchen. Enjoy privacy and beach access. Perfect for a luxurious getaway.
Luxury Waterfront Home Rental Peconic Bay 4 Bedrooms
$ 7500
179, Old Harbor Road, Town of Southold, New York
8 rooms
3500 sq ft
Brand new waterfront home with breathtaking sunrises over Peconic Bay. Four bedrooms, each with its own bathroom, including an expansive primary suite. Large waterfront deck and private beach access. Perfect for luxurious relaxation and entertaining.
