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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, vacation rental in Southold
Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches, vacation rental in Southold
Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches, vacation rental in Southold

Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board, vacation rental in Southold
Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board, vacation rental in Southold
Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board, vacation rental in Southold

Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Welcome to North Fork serenity!, vacation rental in Southold
Welcome to North Fork serenity!, vacation rental in Southold
Welcome to North Fork serenity!, vacation rental in Southold

Welcome to North Fork serenity!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spectacular waterfront property, with magnificent views from all sides., vacation rental in Southold
Spectacular waterfront property, with magnificent views from all sides., vacation rental in Southold
Spectacular waterfront property, with magnificent views from all sides., vacation rental in Southold

Spectacular waterfront property, with magnificent views from all sides.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Family-friendly, dog-friendly modern getaway near wineries and beaches!, vacation rental in Southold
Family-friendly, dog-friendly modern getaway near wineries and beaches!, vacation rental in Southold
Family-friendly, dog-friendly modern getaway near wineries and beaches!, vacation rental in Southold

Family-friendly, dog-friendly modern getaway near wineries and beaches!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Quaint and Quiet cottage. Newly renovated, heated built in pool!, vacation rental in Southold
Quaint and Quiet cottage. Newly renovated, heated built in pool!, vacation rental in Southold
Quaint and Quiet cottage. Newly renovated, heated built in pool!, vacation rental in Southold

Quaint and Quiet cottage. Newly renovated, heated built in pool!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful salt water pool and tiki bar! Walk to the beach and Southold town!, vacation rental in Southold
Beautiful salt water pool and tiki bar! Walk to the beach and Southold town!, vacation rental in Southold
Beautiful salt water pool and tiki bar! Walk to the beach and Southold town!, vacation rental in Southold

Beautiful salt water pool and tiki bar! Walk to the beach and Southold town!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Entertainers Delight Just Steps From The Beach, vacation rental in Southold
Entertainers Delight Just Steps From The Beach, vacation rental in Southold
Entertainers Delight Just Steps From The Beach, vacation rental in Southold

Entertainers Delight Just Steps From The Beach

Rental Home
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Great Location!!  Walk to Town & Train!!, vacation rental in Southold
Great Location!!  Walk to Town & Train!!, vacation rental in Southold
Great Location!!  Walk to Town & Train!!, vacation rental in Southold

Great Location!! Walk to Town & Train!!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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North Fork Beach House, vacation rental in Southold
North Fork Beach House, vacation rental in Southold
North Fork Beach House, vacation rental in Southold

North Fork Beach House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Located in the heart of wine country/BEACHES/shops., vacation rental in Southold
Located in the heart of wine country/BEACHES/shops., vacation rental in Southold
Located in the heart of wine country/BEACHES/shops., vacation rental in Southold

Located in the heart of wine country/BEACHES/shops.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Perfect Family Vacation Home! Charming Waterfront Property close to Vineyards, vacation rental in Southold
Perfect Family Vacation Home! Charming Waterfront Property close to Vineyards, vacation rental in Southold
Perfect Family Vacation Home! Charming Waterfront Property close to Vineyards, vacation rental in Southold

Perfect Family Vacation Home! Charming Waterfront Property close to Vineyards

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront, private beach, ready for adventure, flexcation!, vacation rental in Southold
Waterfront, private beach, ready for adventure, flexcation!, vacation rental in Southold
Waterfront, private beach, ready for adventure, flexcation!, vacation rental in Southold

Waterfront, private beach, ready for adventure, flexcation!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront, New Construction North Fork Beach House, vacation rental in Southold
Waterfront, New Construction North Fork Beach House, vacation rental in Southold
Waterfront, New Construction North Fork Beach House, vacation rental in Southold

Waterfront, New Construction North Fork Beach House

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Southold Soundfront Private Beach, vacation rental in Southold
Southold Soundfront Private Beach, vacation rental in Southold
Southold Soundfront Private Beach, vacation rental in Southold

Southold Soundfront Private Beach

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Kenneys Beach retreat by the Wineries, vacation rental in Southold
Kenneys Beach retreat by the Wineries, vacation rental in Southold
Kenneys Beach retreat by the Wineries, vacation rental in Southold

Kenneys Beach retreat by the Wineries

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beautifully appointed  waterfront property with heated pool and cabana, vacation rental in Southold
Beautifully appointed  waterfront property with heated pool and cabana, vacation rental in Southold
Beautifully appointed  waterfront property with heated pool and cabana, vacation rental in Southold

Beautifully appointed waterfront property with heated pool and cabana

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Renovated American Farmhouse in the heart of Southold with heated saltwater pool, vacation rental in Southold
Renovated American Farmhouse in the heart of Southold with heated saltwater pool, vacation rental in Southold
Renovated American Farmhouse in the heart of Southold with heated saltwater pool, vacation rental in Southold

Renovated American Farmhouse in the heart of Southold with heated saltwater pool

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Three Bed, Three Bath Home Close to Beaches, Vineyards and Breweries, vacation rental in Southold
Three Bed, Three Bath Home Close to Beaches, Vineyards and Breweries, vacation rental in Southold
Three Bed, Three Bath Home Close to Beaches, Vineyards and Breweries, vacation rental in Southold

Three Bed, Three Bath Home Close to Beaches, Vineyards and Breweries

Condo/Apartment
0 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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Southold McCabe's Beach Retreat - Walk to the beach; Relax & enjoy all seasons!, vacation rental in Southold
Southold McCabe's Beach Retreat - Walk to the beach; Relax & enjoy all seasons!, vacation rental in Southold
Southold McCabe's Beach Retreat - Walk to the beach; Relax & enjoy all seasons!, vacation rental in Southold

Southold McCabe's Beach Retreat - Walk to the beach; Relax & enjoy all seasons!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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North Fork Sound Front Beach House, vacation rental in Southold
North Fork Sound Front Beach House, vacation rental in Southold
North Fork Sound Front Beach House, vacation rental in Southold

North Fork Sound Front Beach House

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cute Cottage Apartment Near town, beaches and vineyards (WBH), vacation rental in Southold
Cute Cottage Apartment Near town, beaches and vineyards (WBH), vacation rental in Southold
Cute Cottage Apartment Near town, beaches and vineyards (WBH), vacation rental in Southold

Cute Cottage Apartment Near town, beaches and vineyards (WBH)

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Truly special! Huge North Fork Villa Great for multiple families- Walk to beach, vacation rental in Southold
Truly special! Huge North Fork Villa Great for multiple families- Walk to beach, vacation rental in Southold
Truly special! Huge North Fork Villa Great for multiple families- Walk to beach, vacation rental in Southold

Truly special! Huge North Fork Villa Great for multiple families- Walk to beach

Rental Home
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Unique Southold waterfront luxury home with heated pool on Long Creek, vacation rental in Southold
Unique Southold waterfront luxury home with heated pool on Long Creek, vacation rental in Southold
Unique Southold waterfront luxury home with heated pool on Long Creek, vacation rental in Southold

Unique Southold waterfront luxury home with heated pool on Long Creek

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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FOR SALE — Stroll to Beaches & Town! Beautifully Renovated 1890s Farmhouse, vacation rental in Southold
FOR SALE — Stroll to Beaches & Town! Beautifully Renovated 1890s Farmhouse, vacation rental in Southold
FOR SALE — Stroll to Beaches & Town! Beautifully Renovated 1890s Farmhouse, vacation rental in Southold

FOR SALE — Stroll to Beaches & Town! Beautifully Renovated 1890s Farmhouse

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Northfork home., vacation rental in Southold
Charming Northfork home., vacation rental in Southold
Charming Northfork home., vacation rental in Southold

Charming Northfork home.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Waterfront Home with Outstanding Waterviews!, vacation rental in Southold
Spacious Waterfront Home with Outstanding Waterviews!, vacation rental in Southold
Spacious Waterfront Home with Outstanding Waterviews!, vacation rental in Southold

Spacious Waterfront Home with Outstanding Waterviews!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Classic Arts and Crafts House on the North Fork, vacation rental in Southold
Classic Arts and Crafts House on the North Fork, vacation rental in Southold
Classic Arts and Crafts House on the North Fork, vacation rental in Southold

Classic Arts and Crafts House on the North Fork

Rental Home
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Beautiful Waterfront Paradise In Southold - No Security Deposit, vacation rental in Southold
Beautiful Waterfront Paradise In Southold - No Security Deposit, vacation rental in Southold
Beautiful Waterfront Paradise In Southold - No Security Deposit, vacation rental in Southold

Beautiful Waterfront Paradise In Southold - No Security Deposit

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Midcentury North Fork Beach House walking distance to beach, vacation rental in Southold
Midcentury North Fork Beach House walking distance to beach, vacation rental in Southold
Midcentury North Fork Beach House walking distance to beach, vacation rental in Southold

Midcentury North Fork Beach House walking distance to beach

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Shorecrest Beach House, 4 bedroom private beach front, new renovation, vacation rental in Southold
Shorecrest Beach House, 4 bedroom private beach front, new renovation, vacation rental in Southold
Shorecrest Beach House, 4 bedroom private beach front, new renovation, vacation rental in Southold

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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3 Br North Fork Getaway In Private Beach Community, vacation rental in Southold
3 Br North Fork Getaway In Private Beach Community, vacation rental in Southold
3 Br North Fork Getaway In Private Beach Community, vacation rental in Southold

3 Br North Fork Getaway In Private Beach Community

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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2 Bedroom Apartment in Historic Home with private yard (WBH), vacation rental in Southold
2 Bedroom Apartment in Historic Home with private yard (WBH), vacation rental in Southold
2 Bedroom Apartment in Historic Home with private yard (WBH), vacation rental in Southold

2 Bedroom Apartment in Historic Home with private yard (WBH)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sea Breeze & Sunsets:Beach house steps to Beach & Vineyards, vacation rental in Southold
Sea Breeze & Sunsets:Beach house steps to Beach & Vineyards, vacation rental in Southold
Sea Breeze & Sunsets:Beach house steps to Beach & Vineyards, vacation rental in Southold

Sea Breeze & Sunsets:Beach house steps to Beach & Vineyards

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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AUGUST WEEKS STILL AVAILABLE - Cottage in Private North Fork Beach Community, vacation rental in Southold
AUGUST WEEKS STILL AVAILABLE - Cottage in Private North Fork Beach Community, vacation rental in Southold
AUGUST WEEKS STILL AVAILABLE - Cottage in Private North Fork Beach Community, vacation rental in Southold

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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WATERFRONT Southold Retreat! Steps to Beaches!, vacation rental in Southold
WATERFRONT Southold Retreat! Steps to Beaches!, vacation rental in Southold
WATERFRONT Southold Retreat! Steps to Beaches!, vacation rental in Southold

WATERFRONT Southold Retreat! Steps to Beaches!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES, vacation rental in Southold
PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES, vacation rental in Southold
PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES, vacation rental in Southold

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Updated farmhouse in the heart of wine country.  10 minute drive to Greenport., vacation rental in Southold
Updated farmhouse in the heart of wine country.  10 minute drive to Greenport., vacation rental in Southold
Updated farmhouse in the heart of wine country.  10 minute drive to Greenport., vacation rental in Southold

Updated farmhouse in the heart of wine country. 10 minute drive to Greenport.

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beach Community home nestled in the heart of Long Island's North Fork, vacation rental in Southold
Beach Community home nestled in the heart of Long Island's North Fork, vacation rental in Southold
Beach Community home nestled in the heart of Long Island's North Fork, vacation rental in Southold

Beach Community home nestled in the heart of Long Island's North Fork

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Southold Escape with Large Pool on Wine Trail, vacation rental in Southold
Southold Escape with Large Pool on Wine Trail, vacation rental in Southold
Southold Escape with Large Pool on Wine Trail, vacation rental in Southold

Southold Escape with Large Pool on Wine Trail

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Nature Lover's Paradise on North Fork, vacation rental in Southold
Nature Lover's Paradise on North Fork, vacation rental in Southold
Nature Lover's Paradise on North Fork, vacation rental in Southold

Nature Lover's Paradise on North Fork

Rental Home
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Shelter Bay Cove Waterfront, North Fork , Hamptons ,Long Island, vacation rental in Southold
Shelter Bay Cove Waterfront, North Fork , Hamptons ,Long Island, vacation rental in Southold
Shelter Bay Cove Waterfront, North Fork , Hamptons ,Long Island, vacation rental in Southold

Shelter Bay Cove Waterfront, North Fork , Hamptons ,Long Island

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pristine Oveanview Getaway Sanctuary, vacation rental in Southold
Pristine Oveanview Getaway Sanctuary, vacation rental in Southold
Pristine Oveanview Getaway Sanctuary, vacation rental in Southold

Pristine Oveanview Getaway Sanctuary

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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4 Bed / 2.5 Bath Stunning North Fork retreat with Heated Pool & Hot Tub, vacation rental in Southold
4 Bed / 2.5 Bath Stunning North Fork retreat with Heated Pool & Hot Tub, vacation rental in Southold
4 Bed / 2.5 Bath Stunning North Fork retreat with Heated Pool & Hot Tub, vacation rental in Southold

4 Bed / 2.5 Bath Stunning North Fork retreat with Heated Pool & Hot Tub

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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One Block from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country, vacation rental in Southold
One Block from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country, vacation rental in Southold
One Block from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country, vacation rental in Southold

One Block from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Waterfront with dock on Goose Creek (just off Peconic Bay) and chef's kitchen, vacation rental in Southold
Waterfront with dock on Goose Creek (just off Peconic Bay) and chef's kitchen, vacation rental in Southold
Waterfront with dock on Goose Creek (just off Peconic Bay) and chef's kitchen, vacation rental in Southold

Waterfront with dock on Goose Creek (just off Peconic Bay) and chef's kitchen

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views.., vacation rental in Southold
5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views.., vacation rental in Southold
5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views.., vacation rental in Southold

5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views..

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Southold home at Kenney's Beach 4 bedrooms, vacation rental in Southold
Southold home at Kenney's Beach 4 bedrooms, vacation rental in Southold
Southold home at Kenney's Beach 4 bedrooms, vacation rental in Southold

Southold home at Kenney's Beach 4 bedrooms

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lovely, Serene and Stylish Country Home, vacation rental in Southold
Lovely, Serene and Stylish Country Home, vacation rental in Southold
Lovely, Serene and Stylish Country Home, vacation rental in Southold

Lovely, Serene and Stylish Country Home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport, vacation rental in Southold
Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport, vacation rental in Southold
Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport, vacation rental in Southold

Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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