Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod.

Southold rentals with hot tubs

We found 148 rentals with hot tubs — enter your dates for availability

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December 2025

16

January 2026

Explore Southold rentals with hot tubs

6BR, Saltwater Pool, Bocce, Hot Tub, Sauna. Walk to beach, minutes to vineyards!

Sleeps 10 · 6 bedrooms · 3 bathrooms

Pool

HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern

Sleeps 14 · 6 bedrooms · 4 bathrooms

Pool

Premier Host

Panoramic Water Views, Plunge Pool, Hot Tub, Fire Pit & Walk to Beach

Sleeps 11 · 4 bedrooms · 4+ bathrooms

Heated, salt water gunite pool with hot tub and diving rock.

Luxurious Estate with Pool by Kenney's Beach, McCabe's Beach and Horton's Point

Sleeps 12 · 5 bedrooms · 6 bathrooms

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Holiday Rental options in Southold

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