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Southold Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
155 rentals 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, vacation rental in Southold

Kenneys Beach retreat by the Wineries

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Cottage, vacation rental in Southold
Charming Cottage, vacation rental in Southold
Charming Cottage, vacation rental in Southold

Charming Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Two Bed, Two Bath Home Close to Beaches, Vineyards and Breweries, vacation rental in Southold
Two Bed, Two Bath Home Close to Beaches, Vineyards and Breweries, vacation rental in Southold
Two Bed, Two Bath Home Close to Beaches, Vineyards and Breweries, vacation rental in Southold

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Cottage on North Fork, vacation rental in Southold
Cozy Cottage on North Fork, vacation rental in Southold
Cozy Cottage on North Fork, vacation rental in Southold

Cozy Cottage on North Fork

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Farmhouse Retreat, vacation rental in Southold
Farmhouse Retreat, vacation rental in Southold
Farmhouse Retreat, vacation rental in Southold

Farmhouse Retreat

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Entire Loft-Walk to Town, Beach, Train, Wine Trail, vacation rental in Southold
Entire Loft-Walk to Town, Beach, Train, Wine Trail, vacation rental in Southold
Entire Loft-Walk to Town, Beach, Train, Wine Trail, vacation rental in Southold

Entire Loft-Walk to Town, Beach, Train, Wine Trail

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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KENNEY’s BEACH: SOUTHOLD BEACH COTTAGE Waterview, walk to Beach., vacation rental in Southold
KENNEY’s BEACH: SOUTHOLD BEACH COTTAGE Waterview, walk to Beach., vacation rental in Southold
KENNEY’s BEACH: SOUTHOLD BEACH COTTAGE Waterview, walk to Beach., vacation rental in Southold

KENNEY’s BEACH: SOUTHOLD BEACH COTTAGE Waterview, walk to Beach.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sweet Southold Beach Cottage SPRING/SUMMER/FALL/SEASONAL, vacation rental in Southold
Sweet Southold Beach Cottage SPRING/SUMMER/FALL/SEASONAL, vacation rental in Southold
Sweet Southold Beach Cottage SPRING/SUMMER/FALL/SEASONAL, vacation rental in Southold

Sweet Southold Beach Cottage SPRING/SUMMER/FALL/SEASONAL

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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North Fork Retreat, vacation rental in Southold
North Fork Retreat, vacation rental in Southold
North Fork Retreat, vacation rental in Southold

North Fork Retreat

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Kid-Friendly Home near the Ocean with Private Gas Grill, Fast WiFi, and Cable, vacation rental in Southold
Kid-Friendly Home near the Ocean with Private Gas Grill, Fast WiFi, and Cable, vacation rental in Southold
Kid-Friendly Home near the Ocean with Private Gas Grill, Fast WiFi, and Cable, vacation rental in Southold

Kid-Friendly Home near the Ocean with Private Gas Grill, Fast WiFi, and Cable

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stylish North Fork Getaway on 5 Acre Property, vacation rental in Southold
Stylish North Fork Getaway on 5 Acre Property, vacation rental in Southold
Stylish North Fork Getaway on 5 Acre Property, vacation rental in Southold

Stylish North Fork Getaway on 5 Acre Property

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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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Lake House Located Near North Fork Wineries, vacation rental in Southold
Lake House Located Near North Fork Wineries, vacation rental in Southold
Lake House Located Near North Fork Wineries, vacation rental in Southold

Lake House Located Near North Fork Wineries

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming house walking distance from beautiful Kenney’s Beach, vacation rental in Southold
Charming house walking distance from beautiful Kenney’s Beach, vacation rental in Southold
Charming house walking distance from beautiful Kenney’s Beach, vacation rental in Southold

Charming house walking distance from beautiful Kenney’s Beach

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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)

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming home with fireplace, kayaks, patio, fast WiFi, & washer/dryer-dogs ok, vacation rental in Southold
Charming home with fireplace, kayaks, patio, fast WiFi, & washer/dryer-dogs ok, vacation rental in Southold
Charming home with fireplace, kayaks, patio, fast WiFi, & washer/dryer-dogs ok, vacation rental in Southold

Charming home with fireplace, kayaks, patio, fast WiFi, & washer/dryer-dogs ok

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Classic North Fork Beach Home, vacation rental in Southold
Classic North Fork Beach Home, vacation rental in Southold
Classic North Fork Beach Home, vacation rental in Southold

Classic North Fork Beach Home

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Southold by the bay, vacation rental in Southold
Southold by the bay, vacation rental in Southold
Southold by the bay, vacation rental in Southold

Southold by the bay

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lovely Waterview Cottage in the Heart of Long Island Wine country, vacation rental in Southold
Lovely Waterview Cottage in the Heart of Long Island Wine country, vacation rental in Southold
Lovely Waterview Cottage in the Heart of Long Island Wine country, vacation rental in Southold

Lovely Waterview Cottage in the Heart of Long Island Wine country

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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One Of A Kind, Resort- Like Waterfront Cottage In Wine Country, vacation rental in Southold
One Of A Kind, Resort- Like Waterfront Cottage In Wine Country, vacation rental in Southold
One Of A Kind, Resort- Like Waterfront Cottage In Wine Country, vacation rental in Southold

One Of A Kind, Resort- Like Waterfront Cottage In Wine Country

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful garden-view home near the water with lawn, streaming, W/D, AC, kitchen, vacation rental in Southold
Beautiful garden-view home near the water with lawn, streaming, W/D, AC, kitchen, vacation rental in Southold
Beautiful garden-view home near the water with lawn, streaming, W/D, AC, kitchen, vacation rental in Southold

Beautiful garden-view home near the water with lawn, streaming, W/D, AC, kitchen

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful private home with beach access down the block, vacation rental in Southold
Beautiful private home with beach access down the block, vacation rental in Southold
Beautiful private home with beach access down the block, vacation rental in Southold

Beautiful private home with beach access down the block

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic 2-bedroom upstairs apartment close to beaches, town and vineyards., vacation rental in Southold
Historic 2-bedroom upstairs apartment close to beaches, town and vineyards., vacation rental in Southold
Historic 2-bedroom upstairs apartment close to beaches, town and vineyards., vacation rental in Southold

Historic 2-bedroom upstairs apartment close to beaches, town and vineyards.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Seaside Southold Escape in Private Beach Community, vacation rental in Southold
Seaside Southold Escape in Private Beach Community, vacation rental in Southold
Seaside Southold Escape in Private Beach Community, vacation rental in Southold

Seaside Southold Escape in Private Beach Community

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach, vacation rental in Southold
Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach, vacation rental in Southold
Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach, vacation rental in Southold

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful waterfront house in Southold, vacation rental in Southold
Beautiful waterfront house in Southold, vacation rental in Southold
Beautiful waterfront house in Southold, vacation rental in Southold

Beautiful waterfront house in Southold

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Historic cottage near the NoFo beach, vacation rental in Southold
Historic cottage near the NoFo beach, vacation rental in Southold
Historic cottage near the NoFo beach, vacation rental in Southold

Historic cottage near the NoFo beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cottage on private road and 5-min walk to beach, vacation rental in Southold
Cottage on private road and 5-min walk to beach, vacation rental in Southold
Cottage on private road and 5-min walk to beach, vacation rental in Southold

Cottage on private road and 5-min walk to beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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House central to North Fork wineries restaurants + beaches. Walk to town., vacation rental in Southold
House central to North Fork wineries restaurants + beaches. Walk to town., vacation rental in Southold
House central to North Fork wineries restaurants + beaches. Walk to town., vacation rental in Southold

House central to North Fork wineries restaurants + beaches. Walk to town.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Boutique Waterfront Home with Pool in Heart of North Fork, vacation rental in Southold
Boutique Waterfront Home with Pool in Heart of North Fork, vacation rental in Southold
Boutique Waterfront Home with Pool in Heart of North Fork, vacation rental in Southold

Boutique Waterfront Home with Pool in Heart of North Fork

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Payment Protection
On the Bay!  Your own beach!  Looking out at Shelter Island., vacation rental in Southold
On the Bay!  Your own beach!  Looking out at Shelter Island., vacation rental in Southold
On the Bay!  Your own beach!  Looking out at Shelter Island., vacation rental in Southold

On the Bay! Your own beach! Looking out at Shelter Island.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Enjoy Wine Country and Walk The Beautiful Beach At Sunset, vacation rental in Southold
Enjoy Wine Country and Walk The Beautiful Beach At Sunset, vacation rental in Southold
Enjoy Wine Country and Walk The Beautiful Beach At Sunset, vacation rental in Southold

Enjoy Wine Country and Walk The Beautiful Beach At Sunset

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Enjoy Wine Country and Take Walks On Beautiful, Solitary beaches At Sunset, vacation rental in Southold
Enjoy Wine Country and Take Walks On Beautiful, Solitary beaches At Sunset, vacation rental in Southold
Enjoy Wine Country and Take Walks On Beautiful, Solitary beaches At Sunset, vacation rental in Southold

Enjoy Wine Country and Take Walks On Beautiful, Solitary beaches At Sunset

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Amazing Beach House in the North Fork Wineries, vacation rental in Southold
Amazing Beach House in the North Fork Wineries, vacation rental in Southold
Amazing Beach House in the North Fork Wineries, vacation rental in Southold

Amazing Beach House in the North Fork Wineries

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sunny and quiet home - steps from the bay!, vacation rental in Southold
Sunny and quiet home - steps from the bay!, vacation rental in Southold
Sunny and quiet home - steps from the bay!, vacation rental in Southold

Sunny and quiet home - steps from the bay!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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House of Classic Arts and Crafts North Fork, vacation rental in Southold
House of Classic Arts and Crafts North Fork, vacation rental in Southold
House of Classic Arts and Crafts North Fork, vacation rental in Southold

House of Classic Arts and Crafts North Fork

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Walk to train and town, vacation rental in Southold
Walk to train and town, vacation rental in Southold
Walk to train and town, vacation rental in Southold

Walk to train and town

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Kenney's Beach House, Short Walk to Best Swimming and Sunset Sound Beach, vacation rental in Southold
Kenney's Beach House, Short Walk to Best Swimming and Sunset Sound Beach, vacation rental in Southold
Kenney's Beach House, Short Walk to Best Swimming and Sunset Sound Beach, vacation rental in Southold

Kenney's Beach House, Short Walk to Best Swimming and Sunset Sound Beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Cottage by Cedar Beach, vacation rental in Southold
Cottage by Cedar Beach, vacation rental in Southold
Cottage by Cedar Beach, vacation rental in Southold

Cottage by Cedar Beach

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
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.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Walk to beach! Simple Cottage Bliss. Peaceful & Private., vacation rental in Southold
Walk to beach! Simple Cottage Bliss. Peaceful & Private., vacation rental in Southold
Walk to beach! Simple Cottage Bliss. Peaceful & Private., vacation rental in Southold

Walk to beach! Simple Cottage Bliss. Peaceful & Private.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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3 Bedroom NoFo Home, vacation rental in Southold
3 Bedroom NoFo Home, vacation rental in Southold
3 Bedroom NoFo Home, vacation rental in Southold

3 Bedroom NoFo Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NorthFork Serenity, next to beach and wineries, vacation rental in Southold
NorthFork Serenity, next to beach and wineries, vacation rental in Southold
NorthFork Serenity, next to beach and wineries, vacation rental in Southold

NorthFork Serenity, next to beach and wineries

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Showing results 1-50 of 155
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