Southold Vacation Rentals - HolidayHomes base64Hash Southold Vacation Rentals - HolidayHomes

Southold Vacation Rentals

Browse 33 available vacation homes and compared across 5 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
House with yard, heated pool & hot tub | Nature view
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Cabin Southold
'The Gate House'on Beach front Estate with Dockage. Walk to Village.
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Cabin Southold
Cottage on Beach front Estate Walk to Village
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House Southold
Vacation home with barbecue, garden & patio | Nature view
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House Southold
NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
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House Southold
Beach/Waterfront 7.2 ac Estate with Dockage -40 ft
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House Southold
North Beach Fork Beach House
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House Southold
6BR, Saltwater Pool, walk to beach, hot tub, sauna, minutes from vineyards, town
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House Southold
North Fork, New Construction with heated pool, walking distance to beach
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House Southold
Luxury - 5 bdrs, 6 baths, Tennis Crt, Heated Pool, Basketball, Hot tub, 2.4 acrs
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House Southold
New Suffolk Waterfront Beach Cottage Steps From Water/Beach/Restaurants and More
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House Southold
Children-friendly vacation home with grill & pool
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House Southold
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
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House Southold
House of Classic Arts and Crafts North Fork
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House Southold
Charming updated home with pool on quiet street. Near Silver Beach
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Top 15 most Recommended Vacation Rentals in Southold

Discover your ideal Southold vacation rental with real-time comparisons of 33 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Bed and breakfast Southold
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with garden, patio & pool | Nature view

Southold, Suffolk County, New York, United States
Charming bed and breakfast rental in Southold for 2 guests featuring a cozy fireplace and easy beach access.
from $655
per night
(20)
View deal
Bed and breakfast Southold
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with garden, terrace & heated pool

Southold, Suffolk County, New York, United States
Charming bed and breakfast rental in Southold accommodates 2 guests and features a relaxing hot tub for a perfect getaway.
from $696
per night
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House Southold
House ∙ 12 guests ∙ 6 bedrooms

House with yard & private pool

Southold, Suffolk County, New York, United States
Spacious house rental in Noyack for 12 guests featuring a private pool and a family-friendly atmosphere.
from $361
per night
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House Southold
House ∙ 12 guests ∙ 6 bedrooms

Vacation home with private pool & garden | Good for workation

Southold, Suffolk County, New York, United States
This spacious house rental in Shelter Island Heights accommodates 12 guests and features a private pool for relaxation.
from $807
per night
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House Southold
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with private pool & BBQ | Good for workation

Southold, Suffolk County, New York, United States
This spacious house rental in Shelter Island Heights accommodates 10 guests and features a private pool for a relaxing getaway.
from $524
per night
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House Southold
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented vacation home with patio, yard & barbeque | Nature view | Dogs allowed

Southold, Suffolk County, New York, United States
Charming house rental in Shelter Island Heights accommodates 6 guests and features a cozy fireplace for warm family gatherings.
from $692
per night
(103)
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Cabin Southold
Cabin ∙ 5 guests ∙ 3 bedrooms

Child-friendly cottage with yard, BBQ & terrace

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 $434
per night
(213)
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House Southold
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with yard, barbecue & terrace

Southold, Suffolk County, New York, United States
This house rental in North Fork accommodates 6 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $492
per night
(115)
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House Southold
House ∙ 8 guests ∙ 3 bedrooms

House with barbecue, patio & private pool

Southold, Suffolk County, New York, United States
This house rental in North Fork accommodates 8 guests and features a private pool for a relaxing getaway.
from $596
per night
(17)
View deal

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