The best rentals from the top sites, all in one place

We believe finding a vacation rental in Southold should be easy and not take hours of searching and scrolling. We’ve designed VacationRenter from the ground up to help travelers find the perfect rental faster and easier.

Where to stay in Southold

Vacation rentals in Southold

There are 2,763 vacation rentals near Southold for all manner or mood of travel, availability of time off, and size of budget. So, if you are hoping for an affordable Southold vacation, you can find 10% rentals under $309/night. Or if you are willing to splurge on a luxury vacation in Southold, there are 276 between $1,688 and $9,916/night. Whether you are sleeping by yourself or with a significant other, or are travelling with a group of 123 there are short term home and apartment rentals in Southold to fit your New York vacation needs. The most popular types of short-term rental homes in Southold are houses, apartments and hotels. Southold has been a frequently searched travel destination this year and continues to grow in popularity. VacationRenter offers a wide selection of vacation rental availability from leading travel sites like VRBO (Vacation Rentals By Owner), Homeaway,, and many more. Search your travel dates to find available Southold vacation homes for your trip.

Home-types in Southold

Southold has a variety of property types for you to consider when booking a trip. Here are the most popular property types in Southold:
- Oceanfront2,763 vacation rentals
- Beach2,763 vacation rentals
- House2,482 vacation rentals
- Condo98 vacation rentals
- Apartment98 vacation rentals
- Hotel59 vacation rentals
- Villa56 vacation rentals
- Bed & Breakfast28 vacation rentals
- Resort16 vacation rentals

Points of interests in Southold

Southold has several popular points of interest for you to check out when visiting the area. Here are the most popular points of interest in Southold: