Owner Direct Vacation
Rentals in Southold
The Best Owner Direct Vacation Rentals in Southold. Explore thousands of vacation home rentals, large cabins, and villas near Southold
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Explore the Best Southold Vacation Homes
Looking for the perfect place to stay in Southold? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Southold character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Southold Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Southold
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- Pet Friendly
Popular Neighborhoods for Southold Vacation Rentals
What are the best areas to stay in Southold
Discover the top neighborhoods in Southold and choose a place that suits your stay.
Wednesday Feb 25
Southold, New York
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Southold vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Southold
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How to Reserve Your Southold Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
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Southold Vacation Rental FAQs
1. What are the top vacation rentals in Southold?
There are a lot of options in Southold. If you plan on staying in the Southold area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Southold:
- Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
- Private Coastal Two Bedroom Cottage on the Water
- Family and Dog friendly, private beach⛱️ Amazing Wineries within minutes!
- Family and dog-friendly getaway near amazing wineries, beaches and restaurants!
- Newly Renovated Gem on the Cedar Beach Peninsula!
- Perfect Waterfront Family Vacation Home next to the best vineyards in NY!
- Great Location! Walk to Town & Train!
- Charming Cottage
- Beachfront - endless sunsets, sandy beach, cozy sunroom & open concept kitchen
- Renovated American Farmhouse in the heart of Southold with heated saltwater pool
2. How many vacation rentals have private pools in Southold?
There are 39 vacation rentals with private pools near Southold. Top-rated homes that have access to a swimming pool include:
3. Which vacation homes in Southold are best for families?
If you are looking for a family-friendly vacation home in Southold, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Southold:
4. How many vacation rentals are available in Southold?
Currently, the total number of properties listed in 2026 is over 232 in the Southold area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Southold.