Holiday houses in Southold
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Top-rated holiday rentals in Southold
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Southold holiday rentals
Stay near Southold's top sights
Other great holiday rentals in Southold
Guest favourite
Home in Southold
4.92 out of 5 average rating, 12 reviewsBeach/Lake house Fireplace & Hot Tub, By Wineries
11 – 18 June
$7,482 AUD total
Guest favourite
Home in Southold
5.0 out of 5 average rating, 31 reviewsSalt & Sea House - Near wineries, farms, & beaches
1 – 8 June
$5,041 AUD total
Guest favourite
Cottage in Southold
4.94 out of 5 average rating, 32 reviewsBordeaux meets Côte d’Azur—1763 Historic Farmhouse
17 – 24 Oct
$4,982 AUD total
Guest favourite
Cottage in Southold
4.95 out of 5 average rating, 21 reviewsAdorable Cottage
17 – 24 Nov
$4,581 AUD total
Guest favourite
Home in Greenport
5.0 out of 5 average rating, 35 reviewsBeachfront Greenport Villa
17 – 24 Jan
$6,725 AUD total
Guest favourite
Home in Southold
5.0 out of 5 average rating, 26 reviewsGreenport walk to beach & vineyard! Brand new home
7 – 14 June
$8,106 AUD total
Guest favourite
Home in Greenport
5.0 out of 5 average rating, 30 reviewsHistoric Stunner in Heart of Village
4 – 11 Jan
$6,257 AUD total
Superhost
Cottage in Greenport
4.84 out of 5 average rating, 38 reviewsNewly Renovated 2-Bedroom Home on the LI Sound
8 – 15 Oct
$6,306 AUD total
Quick stats about holiday rentals in Southold
Total rentals
220 properties
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
190 properties are a good fit for families
Total number of reviews
2.7K reviews
Nightly prices starting at
$154 AUD before taxes and fees
Destinations to explore
- New City Accommodation & holiday rentals
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- Martha's Vineyard Holiday rentals
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- Rentals with beach access Southold
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