Vacation Homes in Southold
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Featured Vacation Homes in Southold

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Charming beach home, complete with pool & cozy guest house!

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

New Madison beach house - Ocean front- Great views- booking Summer 2025

Exquisite New Hampton Home in a Perfect Location

The Cooper-Burke House

Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access

Another rental season is coming up.

Historic Coastal Home • Marsh Views • Pet-Friendly
Top trending hotels in Southold

The Shoals Suites and Slips
Vacation Rentals in Southold
What kind of vacation do you want in Southold? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation rental is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Southold that will speak to you.
Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Southold, including luxury vacation rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.
Take a look at what we have on offer. You’ll find rentals close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation rentals a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.
Southold Vacation Homes essential information
Accommodation | 1960 Vacation Homes |
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Lowest Price | CA $135 |
Highest Price | CA $688 |
Popular accommodation | Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor , WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr, Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen, Charming beach home, complete with pool & cozy guest house!, Spacious multiples bedroom house in enchanting Calverton with WiFi, AC, New Madison beach house - Ocean front- Great views- booking Summer 2025, Exquisite New Hampton Home in a Perfect Location, The Cooper-Burke House, Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access, Another rental season is coming up., Historic Coastal Home • Marsh Views • Pet-Friendly, Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom! |