Compare Villas, Resorts, & Rentals in Southold, New York, USA
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 1096.93 ft², with nightly prices averaging CA $987.
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.
Other Places to Stay in Southold, NY
Frequently Asked Questions About Southold?
What are the top holiday rentals in Southold?
- Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
- Private Coastal Two Bedroom Cottage on the Water
- Located in the heart of wine country/BEACHES/shops.
- Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board
- Family and dog-friendly getaway near amazing wineries, beaches and restaurants!
- Perfect Waterfront Family Vacation Home next to the best vineyards in NY!
- Newly Renovated Gem on the Cedar Beach Peninsula!
- Great Location! Walk to Town & Train!
- Beachfront - endless sunsets, sandy beach, cozy sunroom & open concept kitchen
- Renovated American Farmhouse in the heart of Southold with heated saltwater pool
How many Casai.ca 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.
