Woodford County rentals with pool

We found 61 rentals with pool — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

October 2025

1

November 2025

Explore Woodford County rentals with pools

Exterior

Sugar Hill Farm-Historic Horsefarm with Pool

Sleeps 9 · 4 bedrooms · 3 bathrooms

Exterior

Premier Host

Raven Fox Farm-Country Charm! 5 BR Only 8 miles from Keeneland and BG Airport

Sleeps 10 · 5 bedrooms · 2+ bathrooms

Exterior

Barrel Top Bourbon House: Bourbon Trail, Pool, Hot Tub, Speakeasy, Mini-Golf!

Sleeps 8 · 4 bedrooms · 2+ bathrooms

Exterior

Premier Host

High Spirits Estate - Pool, Hot Tub, Game Room, EV charger, Sleeps 20

Sleeps 20 · 7 bedrooms · 5 bathrooms

Find spaces that suit your style

House

Condo/Apartment

Rentals with Pool in Woodford County

Rentals with Pool in Versailles

Rentals with Pool in Midway

Holiday Rental options in Woodford County

Oceanfront holiday rentals in Woodford County

Holiday rentals with spa pool in Woodford County

Pet-friendly holiday rentals in Woodford County

Family-friendly holiday rentals in Woodford County

Beach holiday rentals in Woodford County

Lake holiday rentals in Woodford County

Mountain holiday rentals in Woodford County

Ski holiday rentals in Woodford County

f7f9755d-b538-fe78-63f9-4e93deb68d345480052e-bbe0-42a2-be43-caa116909225