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Southside rentals with pool

We found 2,437 rentals with pool — enter your dates for availability

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December 2025

8

January 2026

Explore Southside rentals with pools

Beach

Oceanfront Villa with Pool, Hot Tub & 5 Condos! USVI

Sleeps 26 · 7 bedrooms · 5 bathrooms

View from Balcony of Oceanfront Pool

Location, Location, Location! 2BR/2BA, Spectacular Ocean and Pool Views

Sleeps 6 · 2 bedrooms · 2 bathrooms

Outdoor dining

Premier Host

Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa

Sleeps 6 · 2 bedrooms · 2 bathrooms

Find spaces that suit your style

House

Condo/Apartment

Holiday Rental options in Southside

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