Southold houses

We found 943 houses — enter your dates for availability

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any holiday home rentals in Southold?
Take your pick of 943 holiday home rentals in Southold that have more space, privacy, value and amenities than the average hotel room. Check out houses in well-known areas such as Greenport West, Silver Beach and The Heights.
How much does it cost to stay in a holiday rental house in Southold?
Explore a wide variety of holiday home rentals in Southold, where there's a price to match every preference. From economical escapes to luxurious properties, Vrbo makes it a cinch to compare options to find the ultimate stay for your next adventure.
When is the best time to rent a holiday house in Southold?
The ideal time to stay in a holiday home rental in Southold depends on you! Begin by checking the weather conditions and temperatures at different times of the year. Also decide whether you prefer to travel in the peak season, shoulder season or off-season.
Where can I rent a Southold holiday house with great views?
Houses with views of historic areas are among the types of holiday home rentals available in Southold. If you're looking for properties that come with vistas to remember, you'll find them on Vrbo.
Does Southold have any weekend house rentals?
Some of our holiday houses can be rented just for the weekend, making them perfect for whirlwind getaways. Enter your desired travel dates to view the availability. You may need to play around with dates and have a little flexibility in your travel plans to find the best holiday home rental in Southold.
Are there any pet-friendly house rentals in Southold?
You bet. There are 12 holiday home rentals where pets are welcome in Southold, so your pooch won't miss out on all the fun. Use our filter tool to find pet-friendly houses that offer perks like dogs beds and free treats for them, and a bunch of cosy conveniences for you.
What are the top things to do in Southold?
Get your Southold escape off to an awesome start by visiting top attractions like The Hamptons Beaches, Orient Point County Park and 67 Steps Beach. Stay in a Vrbo holiday home rental with the family and then discover the best of this destination together.
Why should I book my holiday rental house with Vrbo?
Booking your holiday home rental with Vrbo means you'll have the whole property to yourselves — your own private retreat, with no distractions or interruptions from others. Also, our flexible payment and cancellation policies give you the freedom to change your plans if necessary. Plus, our One Key™ rewards programme lets you collect OneKeyCash™* on any eligible bookings on Vrbo. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo.