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Southold Holiday Rentals

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32 rentals in Southold.
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Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches, holiday rental in Southold

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., holiday rental in Southold

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, holiday rental in Southold

Adorable Southold Cottage in the heart of LI's North Fork ~ Kayak & Paddle Board

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Entertainers Delight Just Steps From The Beach, holiday rental in Southold

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!, holiday rental in Southold

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, holiday rental in Southold

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., holiday rental in Southold

Summer 2021 calendar open! Long term rentals available.

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beachfront home on the North Fork, holiday rental in Southold

Beachfront home on the North Fork

3 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Waterfront on 1 acre, private beach, walk to town, holiday rental in Southold

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, holiday rental in Southold

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, holiday rental in Southold

Shorecrest Beach House, 4 bedroom private beach front, new renovation

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Unique Southold waterfront luxury house and property on Long Creek, 3500 sq.ft., holiday rental in Southold

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, holiday rental in Southold

AUGUST WEEKS STILL AVAILABLE - Cottage in Private North Fork Beach Community

2 bedrooms
2 bathrooms
Sleeps 5
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PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES, holiday rental in Southold

PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES

3 bedrooms
3 bathrooms
Sleeps 6
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Gorgeous Beach House With Stunning 280 Degree Water Views, holiday rental in Southold

Gorgeous Beach House With Stunning 280 Degree Water Views

3 bedrooms
3 bathrooms
Sleeps 10
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Nature Lover's Paradise on North Fork, holiday rental in Southold

Nature Lover's Paradise on North Fork

2 bedrooms
2 bathrooms
Sleeps 5
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Great Relaxing Summer Family  House, holiday rental in Southold

Great Relaxing Summer Family House

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach, holiday rental in Southold

Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach

2 bedrooms
2 bathrooms
Sleeps 6
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Sea Breeze & Sunsets, Private Beach house walk to Vineyards, holiday rental in Southold

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, holiday rental in Southold

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, holiday rental in Southold

Beach Front, spacious 5 Bedrooms, North Fork, Long Island

5 bedrooms
4 bathrooms
Sleeps 12
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Wonderful sunsets overlooking LI Sound!, holiday rental in Southold

Wonderful sunsets overlooking LI Sound!

4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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3 Br North Fork Getaway In Private Beach Community, holiday rental in Southold

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, holiday rental in Southold

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, holiday rental in Southold

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, holiday rental in Southold

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, holiday rental in Southold

The perfect north fork experience

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Southold Country Home, close to Wineries, Apple & Pumpkin Picking & Festivals, holiday rental in Southold

Southold Country Home, close to Wineries, Apple & Pumpkin Picking & Festivals

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Southold Soundfront Private Beach, holiday rental in Southold

Southold Soundfront Private Beach

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious Northfork Home w/ Heated Saltwater Pool, holiday rental in Southold

Spacious Northfork Home w/ Heated Saltwater Pool

4 bedrooms
3 bathrooms
Sleeps 12
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Charming English Tudor, holiday rental in Southold

Charming English Tudor

4 bedrooms
3 bathrooms
Sleeps 10
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Brand New Apartment Across From Town Beach, holiday rental in Southold

Brand New Apartment Across From Town Beach

2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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