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Southold
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Vacation Rentals in Southold, NY
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Kid friendly (122)
Pet friendly (50)
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Waterfront (38)
Boat Available (6)
Water Views (5)
Ocean Views (2)
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Distance from
1 mi
140 rentals
in Southold.
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Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches
136 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
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Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board
43 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Welcome to North Fork serenity!
39 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Spectacular waterfront property, with magnificent views from all sides.
37 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Family-friendly, dog-friendly modern getaway near wineries and beaches!
26 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Quaint and Quiet cottage. Newly renovated, heated built in pool!
23 reviews
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!
22 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 11
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Entertainers Delight Just Steps From The Beach
23 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 14
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Great Location!! Walk to Town & Train!!
23 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 3
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North Fork Beach House
25 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Located in the heart of wine country/BEACHES/shops.
22 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Perfect Family Vacation Home! Charming Waterfront Property close to Vineyards
21 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Waterfront, private beach, ready for adventure, flexcation!
14 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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Waterfront, New Construction North Fork Beach House
14 reviews
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Southold Soundfront Private Beach
14 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Kenneys Beach retreat by the Wineries
14 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
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Beautifully appointed waterfront property with heated pool and cabana
19 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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Renovated American Farmhouse in the heart of Southold with heated saltwater pool
14 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Three Bed, Three Bath Home Close to Beaches, Vineyards and Breweries
12 reviews
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!
11 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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North Fork Sound Front Beach House
11 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
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Cute Cottage Apartment Near town, beaches and vineyards (WBH)
12 reviews
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
14 reviews
Rental Home
6 bedrooms
5 bathrooms
Sleeps 14
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Unique Southold waterfront luxury home with heated pool on Long Creek
15 reviews
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
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FOR SALE — Stroll to Beaches & Town! Beautifully Renovated 1890s Farmhouse
9 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Charming Northfork home.
10 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Spacious Waterfront Home with Outstanding Waterviews!
10 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
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Classic Arts and Crafts House on the North Fork
8 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 3
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Beautiful Waterfront Paradise In Southold - No Security Deposit
7 reviews
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
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Midcentury North Fork Beach House walking distance to beach
7 reviews
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Shorecrest Beach House, 4 bedroom private beach front, new renovation
3 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
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3 Br North Fork Getaway In Private Beach Community
10 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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2 Bedroom Apartment in Historic Home with private yard (WBH)
18 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Sea Breeze & Sunsets:Beach house steps to Beach & Vineyards
12 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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AUGUST WEEKS STILL AVAILABLE - Cottage in Private North Fork Beach Community
6 reviews
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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WATERFRONT Southold Retreat! Steps to Beaches!
6 reviews
Rental Home
4 bedrooms
4 bathrooms
Sleeps 16
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PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES
4 reviews
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.
5 reviews
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
4 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Southold Escape with Large Pool on Wine Trail
4 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Nature Lover's Paradise on North Fork
5 reviews
Rental Home
2 bedrooms
2 bathrooms
Sleeps 2
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Shelter Bay Cove Waterfront, North Fork , Hamptons ,Long Island
3 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Pristine Oveanview Getaway Sanctuary
2 reviews
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
2 reviews
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
3 reviews
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
4 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views..
2 reviews
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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Southold home at Kenney's Beach 4 bedrooms
2 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Lovely, Serene and Stylish Country Home
2 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
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Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
2 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Frequently Asked Questions about Southold
Do any vacation rentals in Southold have a pool?
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
See all vacation rentals with a pool in Southold on Tripadvisor
Do any vacation rentals in Southold have internet access?
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
See all vacation rentals in Southold on Tripadvisor
What are the best pet friendly rentals in Southold?
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
See all pet friendly vacation rentals in Southold on Tripadvisor
What are some great rentals in Southold that are kid friendly?
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)
See all kid friendly vacation rentals in Southold on Tripadvisor