Southold Vacation Rentals
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140 rentals in Southold.
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Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches
Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
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Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Welcome to North Fork serenity!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Spectacular waterfront property, with magnificent views from all sides.
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Family-friendly, dog-friendly modern getaway near wineries and beaches!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Quaint and Quiet cottage. Newly renovated, heated built in pool!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Beautiful salt water pool and tiki bar! Walk to the beach and Southold town!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 11
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Entertainers Delight Just Steps From The Beach
Rental Home
4 bedrooms
3 bathrooms
Sleeps 14
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Great Location!! Walk to Town & Train!!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 3
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North Fork Beach House
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Located in the heart of wine country/BEACHES/shops.
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Perfect Family Vacation Home! Charming Waterfront Property close to Vineyards
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Waterfront, private beach, ready for adventure, flexcation!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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Waterfront, New Construction North Fork Beach House
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Southold Soundfront Private Beach
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Kenneys Beach retreat by the Wineries
Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
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Beautifully appointed waterfront property with heated pool and cabana
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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Renovated American Farmhouse in the heart of Southold with heated saltwater pool
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Three Bed, Three Bath Home Close to Beaches, Vineyards and Breweries
Condo/Apartment
0 bedrooms
3 bathrooms
Sleeps 3
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Southold McCabe's Beach Retreat - Walk to the beach; Relax & enjoy all seasons!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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North Fork Sound Front Beach House
Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
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Cute Cottage Apartment Near town, beaches and vineyards (WBH)
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Truly special! Huge North Fork Villa Great for multiple families- Walk to beach
Rental Home
6 bedrooms
5 bathrooms
Sleeps 14
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Unique Southold waterfront luxury home with heated pool on Long Creek
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
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FOR SALE — Stroll to Beaches & Town! Beautifully Renovated 1890s Farmhouse
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Charming Northfork home.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Spacious Waterfront Home with Outstanding Waterviews!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
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Classic Arts and Crafts House on the North Fork
Rental Home
3 bedrooms
2 bathrooms
Sleeps 3
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Beautiful Waterfront Paradise In Southold - No Security Deposit
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
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Midcentury North Fork Beach House walking distance to beach
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Shorecrest Beach House, 4 bedroom private beach front, new renovation
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
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3 Br North Fork Getaway In Private Beach Community
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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2 Bedroom Apartment in Historic Home with private yard (WBH)
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Sea Breeze & Sunsets:Beach house steps to Beach & Vineyards
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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AUGUST WEEKS STILL AVAILABLE - Cottage in Private North Fork Beach Community
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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WATERFRONT Southold Retreat! Steps to Beaches!
Rental Home
4 bedrooms
4 bathrooms
Sleeps 16
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PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Updated farmhouse in the heart of wine country. 10 minute drive to Greenport.
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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Beach Community home nestled in the heart of Long Island's North Fork
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Southold Escape with Large Pool on Wine Trail
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Nature Lover's Paradise on North Fork
Rental Home
2 bedrooms
2 bathrooms
Sleeps 2
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Shelter Bay Cove Waterfront, North Fork , Hamptons ,Long Island
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Pristine Oveanview Getaway Sanctuary
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
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4 Bed / 2.5 Bath Stunning North Fork retreat with Heated Pool & Hot Tub
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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One Block from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
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Waterfront with dock on Goose Creek (just off Peconic Bay) and chef's kitchen
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views..
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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Southold home at Kenney's Beach 4 bedrooms
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Lovely, Serene and Stylish Country Home
Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
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Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Frequently Asked Questions about Southold
- Yes, here are some popular vacation rentals in Southold that have a pool:
- Steve's Place: Heated Pool, 3BR Southold Home, Beach
- PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES
- Private Waterfront W Beach, New Renovation
- Yes, here are some popular vacation rentals in Southold that have internet access:
- PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES
- Private Waterfront W Beach, New Renovation
- Shorecrest Beach House, 4 bedroom private beach front, new renovation
- The best pet friendly rentals in Southold are:
- Private Waterfront W Beach, New Renovation
- Shorecrest Beach House, 4 bedroom private beach front, new renovation
- Panoramic Water Views, hot tub, fire pit & easy access to North Fork wine trail
- Some of the most popular kid friendly rentals in Southold are:
- PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES
- Panoramic Water Views, hot tub, fire pit & easy access to North Fork wine trail
- Cute Cottage Apartment Near town, beaches and vineyards (WBH)