Southold Vacation Rentals - HolidayHomes base64Hash Southold Vacation Rentals - HolidayHomes

Southold Vacation Rentals

Browse 189 available vacation homes and compared across 8 trusted partners

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Top-Rated Vacation rentals in Southold

Book the highest-rated Southold vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Southold
6BR, Saltwater Pool, Bocce, Hot Tub, Sauna. Walk to beach, minutes to vineyards!
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House Southold
Family-friendly nice vacation home with garden, terrace & private pool | Nature view | Suitable for remote work | Pets allowed
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House Southold
Shorecrest Beach House Beach Front Ocean views
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House Southold
Heated pool on Goose Creek, private dock, massive yard walk to beach, wineries
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House Southold
Southold Soundfront Private Beach
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House Southold
Waterfront, New Construction North Fork Beach House
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House Southold
Between the Vineyard and Sea. Walk to sandy beach from this charming cottage.
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House Southold
House with garden, private pool & grill
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House Southold
Southold, NY- Heart of North Fork Wine Country and Minutes From The Beach
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House Southold
Southold Escape with Large Saltwater Pool on Wine Trail
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House Southold
Vacation home with terrace, yard & barbeque
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House Southold
Vacation home with jacuzzi, patio & private pool
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House Southold
Family-friendly vacation home with BBQ, private pool & patio | Suitable for remote work | Pets allowed
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House Southold
House with private pool, grill & yard
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House Southold
Beautiful Southold Home with a Water View - 3 Bedroom, 2.5 Bath, Sleeps 8
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Top 15 most Recommended Vacation Rentals in Southold

Discover your ideal Southold vacation rental with real-time comparisons of 189 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Southold
House ∙ 4 guests ∙ 2 bedrooms

74 m² House

Southold, Suffolk County, New York, United States
This charming house rental in North Fork accommodates 4 guests and features a cozy fireplace for relaxing evenings.
from $223
per night
(21)
View deal
House Southold
House ∙ 9 guests ∙ 4 bedrooms

333 m² House

Southold, Suffolk County, New York, United States
This house rental in North Fork accommodates 9 guests and features a hot tub for relaxation.
from $449
per night
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Cabin Southold
Cabin ∙ 8 guests ∙ 3 bedrooms

135 m² Cabin

Southold, Suffolk County, New York, United States
This cozy cabin in North Fork accommodates 8 guests and features convenient beach access for a perfect getaway.
from $784
per night
(40)
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House Southold
House ∙ 8 guests ∙ 4 bedrooms

195 m² House

Southold, Suffolk County, New York, United States
This house rental in North Fork accommodates 8 guests and features a family-friendly kitchen.
from $668
per night
(52)
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House Southold
6 guests ∙ 3 bedrooms

House

Southold, Suffolk County, New York, United States
This house rental in North Fork accommodates 6 guests and features a private pool for your enjoyment.
from $767
per night
(8)
View deal
House Southold
6 guests ∙ 3 bedrooms

House

Southold, Suffolk County, New York, United States
This house rental in North Fork accommodates 6 guests and features a private pool for relaxation and enjoyment.
from $217
per night
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House Southold
House ∙ 8 guests ∙ 4 bedrooms

186 m² House

Southold, Suffolk County, New York, United States
This house rental in North Fork accommodates 8 guests and features a spacious yard perfect for outdoor gatherings.
from $580
per night
(5)
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Cabin Southold
5 guests ∙ 3 bedrooms

Cabin

Southold, Suffolk County, New York, United States
Charming cabin in North Fork accommodates 4 guests and features a cozy fireplace for a perfect getaway.
from $224
per night
(10)
View deal
Cabin Southold
Cabin ∙ 5 guests ∙ 3 bedrooms

139 m² Cabin

Southold, Suffolk County, New York, United States
This cozy cabin in North Fork accommodates 5 guests and features a welcoming fireplace for a warm and inviting atmosphere.
from $411
per night
(211)
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