Madison County rentals with pool

We found 80 rentals with pool — enter your dates for availability

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December 2025

January 2026

Explore Madison County rentals with pools

Showing deals for: 20 Feb - 23 Feb

Gate and front door to private guest house

Premier Host

You will love your stay here, everyone does!

Sleeps 6 · 1 bedroom · 1 bathroom

for 3 nights, 1 home

NZ$354 per night

includes taxes & fees

basketball court, and side view of property

Elegant house pool, sports, pizza & boat bar, business center, mini theater.

Sleeps 16 · 7 bedrooms · 1+ bathroom

for 3 nights, 1 home

NZ$881 per night

includes taxes & fees

Bees Knees has exclusive use of the private backyard pool and both the Mill Haus and the Beekeeper's Cottage

Premier Host

Bee's Knees - Private Heated Pool and Hot Tub, Dog Friendly, Wineries

Sleeps 20 · 7 bedrooms · 5+ bathrooms

for 3 nights, 1 home

NZ$2,170 per night

includes taxes & fees

Elegant home with pool, fenced yard, full kitchen & theater.

Sleeps 24 · 6 bedrooms · 2 bathrooms

for 3 nights, 1 home

NZ$795 per night

includes taxes & fees

Premier Host

Arch View Luxury Home 5 minutes to St. Louis:Private Pool,Sauna,Free Wine&Brkfst

Sleeps 6 · 3 bedrooms · 2+ bathrooms

for 3 nights, 1 home

NZ$1,099 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Explore Madison County rentals with pools

You will love your stay here, everyone does!

Elegant house pool, sports, pizza & boat bar, business center, mini theater.

Bee's Knees - Private Heated Pool and Hot Tub, Dog Friendly, Wineries

Peaceful ONE bedroom Apartment with at home gym

Elegant home with pool, fenced yard, full kitchen & theater.

Arch View Luxury Home 5 minutes to St. Louis:Private Pool,Sauna,Free Wine&Brkfst

Find spaces that suit your style

Rentals with Pool in Madison County

Holiday Rental options in Madison County