Photo by Summer Williams

Madison County rentals with pool

We found 13 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: 21 Feb - 24 Feb

Cafe Exterior (Courtyard Suite entrance on upper deck)

Premier Host

Pickleball Cafe & Micro Hotel

Sleeps 6 · 1 bedroom · 1 bathroom

for 3 nights, 1 apartment

NZ$372 per night

includes taxes & fees

Premier Host

Authentic Cedar Cabin-Dogwood Cabin-with Pool near Blue Springs Ranch

Sleeps 12 · 5 bedrooms · 2 bathrooms

for 3 nights, 1 cabin

NZ$1,192 per night

includes taxes & fees

Falls Hideaway Chalet view from the lakeside dock

Premier Host

Innsbrook Falls Hideaway - Roomy lakefront Chalet w/ spacious deck & firepit

Sleeps 9 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 chalet

NZ$515 per night

includes taxes & fees

Premier Host

Spacious Five Bedroom Country Home Near Hermann MO

Sleeps 13 · 5 bedrooms · 3 bathrooms

for 3 nights, 1 room

NZ$1,198 per night

includes taxes & fees

In ground pool opens in May. Closes in September.

Premier Host

Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE

Sleeps 11 · 4 bedrooms · 2+ bathrooms

for 3 nights, 1 home

NZ$946 per night

includes taxes & fees

Find spaces that suit your style

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Condo/Apartment

Explore Madison County rentals with pools

Pickleball Cafe & Micro Hotel

Mountain View at Pickle & Perk

Authentic Cedar Cabin-Dogwood Cabin-with Pool near Blue Springs Ranch

Innsbrook Falls Hideaway - Roomy lakefront Chalet w/ spacious deck & firepit

Spacious Five Bedroom Country Home Near Hermann MO

Bluebird Meadows with In-ground Pool and Hot Tub! 125 ACRES TO EXPLORE

Find spaces that suit your style

Rentals with Pool in Madison County

Holiday Rental options in Madison County