Southold Vacation Rentals
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
155 rentals in Southold.
Kenneys Beach retreat by the Wineries
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Renovated American Farmhouse in the heart of Southold with heated saltwater pool
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Cottage
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Two Bed, Two Bath Home Close to Beaches, Vineyards and Breweries
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Cottage on North Fork
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Farmhouse Retreat
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Southold Soundfront Private Beach
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Entire Loft-Walk to Town, Beach, Train, Wine Trail
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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KENNEY’s BEACH: SOUTHOLD BEACH COTTAGE Waterview, walk to Beach.
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sweet Southold Beach Cottage SPRING/SUMMER/FALL/SEASONAL
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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North Fork Retreat
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Kid-Friendly Home near the Ocean with Private Gas Grill, Fast WiFi, and Cable
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stylish North Fork Getaway on 5 Acre Property
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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2 Bedroom Apartment in Historic Home with private yard (WBH)
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lake House Located Near North Fork Wineries
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming house walking distance from beautiful Kenney’s Beach
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cute Cottage Apartment Near town, beaches and vineyards (WBH)
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming home with fireplace, kayaks, patio, fast WiFi, & washer/dryer-dogs ok
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Classic North Fork Beach Home
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Southold by the bay
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lovely Waterview Cottage in the Heart of Long Island Wine country
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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One Of A Kind, Resort- Like Waterfront Cottage In Wine Country
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful garden-view home near the water with lawn, streaming, W/D, AC, kitchen
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful private home with beach access down the block
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic 2-bedroom upstairs apartment close to beaches, town and vineyards.
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Seaside Southold Escape in Private Beach Community
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful waterfront house in Southold
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Historic cottage near the NoFo beach
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cottage on private road and 5-min walk to beach
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Midcentury North Fork Beach House walking distance to beach
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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House central to North Fork wineries restaurants + beaches. Walk to town.
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Boutique Waterfront Home with Pool in Heart of North Fork
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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On the Bay! Your own beach! Looking out at Shelter Island.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Enjoy Wine Country and Walk The Beautiful Beach At Sunset
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Enjoy Wine Country and Take Walks On Beautiful, Solitary beaches At Sunset
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Amazing Beach House in the North Fork Wineries
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sunny and quiet home - steps from the bay!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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House of Classic Arts and Crafts North Fork
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Walk to train and town
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Kenney's Beach House, Short Walk to Best Swimming and Sunset Sound Beach
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Cottage by Cedar Beach
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Charming Northfork home.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Walk to beach! Simple Cottage Bliss. Peaceful & Private.
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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3 Bedroom NoFo Home
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NorthFork Serenity, next to beach and wineries
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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North Fork Beach House
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely, Serene and Stylish Country Home
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Showing results 1-50 of 155
Frequently Asked Questions about Southold
- Yes, here are some popular vacation rentals in Southold that have a pool:
- Boutique Waterfront Home with Pool in Heart of North Fork
- Steve's Place: Heated Pool, 3BR Southold Home, Beach
- Kenneys Beach retreat by the Wineries
- Yes, here are some popular vacation rentals in Southold that have internet access:
- Kenneys Beach retreat by the Wineries
- Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches
- Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board
- Some of the most popular kid friendly rentals in Southold are:
- Kenneys Beach retreat by the Wineries
- Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches
- Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board