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Search results showing properties in Southold, New York, United States of America

Google map showing 500 properties

Premier Host
Cottage · 4 min drive to the beach

Quaint Cottage Close to LI Sound

Sleeps 3 · 2 bedrooms · 1 bathroom
Private host
9.8 out of 10
exceptional
(122 reviews)
Unavailable
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House · 2 min drive to the beach

A Natural Getaway

Sleeps 6 · 3 bedrooms · 2+ bathrooms
Private host
10 out of 10
exceptional
(3 reviews)
Unavailable
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Premier Host
Cottage · 5 min drive to the beach

Private Coastal Two Bedroom Cottage on the Water

Sleeps 6 · 2 bedrooms · 1+ bathroom
Private host
10 out of 10
exceptional
(62 reviews)
Unavailable
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Cottage · 13 min walk to Horton Lane Beach

Lovely Waterview Cottage in the Heart of Long Island Wine country

Sleeps 4 · 2 bedrooms · 2 bathrooms
Private host
10 out of 10
exceptional
(15 reviews)
Unavailable
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Cottage · 6 min drive to the beach

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

Sleeps 4 · 2 bedrooms · 1 bathroom
Private host
10 out of 10
exceptional
(62 reviews)
Unavailable
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Cottage · 5 min drive to the beach

Charming Cottage

Sleeps 4 · 2 bedrooms · 1 bathroom
Private host
10 out of 10
exceptional
(14 reviews)
Unavailable
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Cottage · 5 min drive to the beach

Fabulous Waterfront Property in the Heart of Wine Country

Sleeps 5 · 3 bedrooms · 1 bathroom
Private host
10 out of 10
exceptional
(153 reviews)
Unavailable
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House · 8 min drive to the beach

Perfect Waterfront Family Vacation Home next to the best vineyards in NY!

Sleeps 8 · 3 bedrooms · 3 bathrooms
Private host
10 out of 10
exceptional
(26 reviews)
Unavailable
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House · 5 min drive to the beach

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

Sleeps 4 · 2 bedrooms · 1 bathroom
10 out of 10
exceptional
(1 review)
Unavailable
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House · 8 min drive to the beach

Lovely 4 Bedroom Southold Home Walking Distance to Peconic Bay

Sleeps 6 · 4 bedrooms · 1+ bathroom
Private host
10 out of 10
exceptional
(1 review)
Unavailable
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House · 5 min drive to the beach

Secluded charmer with new heated gunnite pool and steps to beach!

Sleeps 7 · 3 bedrooms · 2 bathrooms
Private host
10 out of 10
exceptional
(2 reviews)
Unavailable
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House · 9 min walk to Horton Lane Beach

Charming house walking distance from beautiful Kenney’s Beach

Sleeps 4 · 2 bedrooms · 1 bathroom
Private host
10 out of 10
exceptional
(3 reviews)
Unavailable
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House · 5 min drive to the beach

Sea Breeze Paradise: Beachfront & Panoramic Views

Sleeps 6 · 3 bedrooms · 2 bathrooms
9.4 out of 10
exceptional
(16 reviews)
Unavailable
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House · 11 min drive to the beach

Monthly rental discount of 20% 3 minute walk from a private beach!

Sleeps 12 · 4 bedrooms · 2 bathrooms
Private host
10 out of 10
exceptional
(5 reviews)
Unavailable
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House · 8 min drive to the beach

Waterfront, private beach, ready for adventure, light & bright!

Sleeps 10 · 4 bedrooms · 2+ bathrooms
Private host
10 out of 10
exceptional
(16 reviews)
Unavailable
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House · 9 min drive to the beach

Dog-friendly, comfortable home with private pool, large yard, WiFi, & fire pit

Sleeps 8 · 3 bedrooms · 2+ bathrooms
Unavailable
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House · 8 min drive to the beach

Family and dog-friendly getaway near amazing wineries, beaches and restaurants!

Sleeps 8 · 4 bedrooms · 2 bathrooms
Private host
10 out of 10
exceptional
(37 reviews)
Unavailable
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House · 5 min drive to the beach

Heated pool on Goose Creek, private dock, massive yard walk to beach, wineries

Sleeps 7 · 3 bedrooms · 2+ bathrooms
Private host
9.8 out of 10
exceptional
(21 reviews)
Unavailable
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