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Southold Holiday Vacation with Pools

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33 rentals in Southold.
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Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches
3 bedrooms
2 bathrooms
Sleeps 10
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Spectacular waterfront property, with magnificent views from all sides.
3 bedrooms
3 bathrooms
Sleeps 8
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Adorable Southold Cottage in the heart of LI's North Fork ~ Kayak & Paddle Board
2 bedrooms
2 bathrooms
Sleeps 4
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Beachfront home on the North Fork
3 bedrooms
4 bathrooms
Sleeps 12
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Entertainers Delight Just Steps From The Beach
4 bedrooms
3 bathrooms
Sleeps 14
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Quaint and Quiet cottage. Newly renovated, heated built in pool!
2 bedrooms
2 bathrooms
Sleeps 4
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Curated Country Living In A Historic Farmhouse
3 bedrooms
3 bathrooms
Sleeps 7
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Summer 2021 calendar open! Long term rentals available.
4 bedrooms
2 bathrooms
Sleeps 8
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Waterfront on 1 acre, private beach, walk to town
4 bedrooms
3 bathrooms
Sleeps 11
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Classic Arts and Crafts House on the North Fork
3 bedrooms
2 bathrooms
Sleeps 6
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Shorecrest Beach House, 4 bedroom private beach front, new renovation
4 bedrooms
2 bathrooms
Sleeps 10
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Unique Southold waterfront luxury house and property on Long Creek, 3500 sq.ft.
4 bedrooms
4 bathrooms
Sleeps 10
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AUGUST WEEKS STILL AVAILABLE - Cottage in Private North Fork Beach Community
2 bedrooms
2 bathrooms
Sleeps 5
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Gorgeous Beach House With Stunning 280 Degree Water Views
3 bedrooms
3 bathrooms
Sleeps 10
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PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES
3 bedrooms
3 bathrooms
Sleeps 6
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Nature Lover's Paradise on North Fork
2 bedrooms
2 bathrooms
Sleeps 5
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Great Relaxing Summer Family House
5 bedrooms
3 bathrooms
Sleeps 12
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Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach
2 bedrooms
2 bathrooms
Sleeps 6
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Southold Soundfront Private Beach
2 bedrooms
1 bathroom
Sleeps 4
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Sea Breeze & Sunsets, Private Beach house walk to Vineyards
3 bedrooms
2 bathrooms
Sleeps 8
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Private Waterfront W Beach, New Renovation
3 bedrooms
3 bathrooms
Sleeps 8
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Beach Front, spacious 5 Bedrooms, North Fork, Long Island
5 bedrooms
4 bathrooms
Sleeps 12
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Brand New Apartment Across From Town Beach
2 bedrooms
3 bathrooms
Sleeps 5
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Wonderful sunsets overlooking LI Sound!
4 bedrooms
4 bathrooms
Sleeps 6
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3 Br North Fork Getaway In Private Beach Community
3 bedrooms
2 bathrooms
Sleeps 8
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Beautiful Southold Home with a Water View - 3 Bedroom, 2.5 Bath, Sleeps 8
3 bedrooms
3 bathrooms
Sleeps 8
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Brand New Construction - Beaches, Hiking, Wineries, Farms, Fine Dining
4 bedrooms
4 bathrooms
Sleeps 8
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Waterfront with dock on Goose Creek (just off Peconic Bay) and chef's kitchen
3 bedrooms
3 bathrooms
Sleeps 6
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The perfect north fork experience
6 bedrooms
5 bathrooms
Sleeps 14
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Southold Country Home, close to Wineries, Apple & Pumpkin Picking & Festivals
3 bedrooms
4 bathrooms
Sleeps 8
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Spacious Northfork Home w/ Heated Saltwater Pool
4 bedrooms
3 bathrooms
Sleeps 12
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Charming English Tudor
4 bedrooms
3 bathrooms
Sleeps 10
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3BR Newly renovated Southold Beach Cottage steps to beach village Greenport
3 bedrooms
1 bathroom
Sleeps 5
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