Southold Vacation Rentals

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Vacation Rentals in Southold

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Southold Vacation Rentals essential information

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1873 Vacation Rentals
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Waterfront House with picture-perfect views from all 3 levels., WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr, 10 Bedroom Hampton House with a regulation size Pickleball, Large Charming Historic House close to Beaches, Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included, Charming Village home in the heart of Southampton, Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi, Sprawling Southampton Home: Private Pool, Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!, Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖 , New Madison beach house - Ocean front- Great views- booking Summer 2025, Unique location fenced in private beach