229+ Private Villas and Holiday Rentals in Southold |
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Southold Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Southold

Discover more than 229 vacation rentals available in Southold. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Southold.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Southold, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Southold. On average, places to stay near Southold offer 1091.7 ft², with nightly prices averaging GB £526.

With Casai, finding and comparing holiday rentals in Southold is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Southold

Type Count
Vacation Homes 189
Cottages 20
Holiday Apartments 5

Use these Quick Filters to Find a Holiday Rental in Southold

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Southold.

Weather in Southold, NY

View the weather forecast for Southold before booking your Southold Vacation Rentals to confirm your best time to go.

December - February
High 42°F       Low 22°F
March - May
High 65°F       Low 23°F
June - August
High 79°F       Low 58°F
September - November
High 75°F       Low 32°F

Top Attractions Around Southold, NY

Casai offers a large selection of top attractions around Southold . Research things to do on your vacation before you visit Southold.


Sparkling Pointe
The Old Field Vineyards
Mattebella Vineyards
Horton Point Park
Sannino's Bella Vita Vineyard
Croteaux Vineyards
Osprey's Dominion
Horton Lane Beach
Cooper's Beach
Splish Splash Water Park
Essex Steam Train
East Hampton Main Beach
Wolffer Estates Vineyard
Hammonasset Beach State Park
Tanger Outlet Center
Meschutt Beach
Guild Hall
Essex Library
Hither Hills State Park
Clinton Crossing Premium Outlets

Other Places to Stay in Southold, NY


The Old Field Vineyards 375 Properties
Croteaux Vineyards 296 Properties
Mattebella Vineyards 295 Properties
Osprey's Dominion 291 Properties
Sannino's Bella Vita Vineyard 279 Properties
Sparkling Pointe 260 Properties
Horton Lane Beach 202 Properties
Horton Point Park 183 Properties

Frequently Asked Questions About Southold?

What are the top holiday rentals in Southold?

With numerous options available in Southold, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Southold:

How many holiday rentals have private pools in Southold?

Discover a selection of holiday rentals with private pools near Southold with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Southold are best for families?

If you're searching for a family-friendly holiday home in Southold, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Southold:

How many Casai.uk holiday rentals are available in Southold?

As of 2025, Casai boasts over 229 properties listed in the Southold area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Southold.


People Also Ask

There are 229 Southold, NY Holiday Rentals

Recently Booked Holiday Rentals in Southold