Town of Southold Town oceanfront rentals

We found 1,312 oceanfront rentals — enter your dates for availability

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September 2025

October 2025

Explore Town of Southold Town ocean view rentals

Premier Host

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

Sleeps 6 · 2 bedrooms · 1+ bathroom

Beautifully appointed waterfront property with heated pool and cabana

Sleeps 10 · 4 bedrooms · 3 bathrooms

A typical summer day at the sandy Peconic Bay, fishing, clamming & swimming

Premier Host

It’s All About the Beach ~ 3 minute walk to private sandy Bay Beach

Sleeps 6 · 2 bedrooms · 2 bathrooms

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Holiday Rental options in Town of Southold Town

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