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Madison County family rentals

We found 154 family rentals — enter your dates for availability

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November 2025

December 2025

Find the best place to stay - Madison County

Showing deals for: 9 Feb - 12 Feb

Premier Host

Holliwell Bridge Retreat - Private, Spacious & Close to town! Great for Groups!

Sleeps 12 · 5 bedrooms · 2+ bathrooms

for 3 nights, 1 home

AU$579 per night

includes taxes & fees

Charming 1855 Stone Farmhouse Retreat – Cozy Stays & Picturesque Views Await

Sleeps 8 · 4 bedrooms · 1 bathroom

for 3 nights, 1 room

AU$556 per night

includes taxes & fees

Premier Host

Sleeps 12…. 5 beds and a sofa sleeper. 20 min from West Des Moines..

Sleeps 12 · 5 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$279 per night

includes taxes & fees

Premier Host

Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

Sleeps 10 · 3 bedrooms · 3 bathrooms

for 3 nights, 1 home

AU$392 per night

includes taxes & fees

Sunset from the living room picture window

Premier Host

Serenity Heights - Peaceful Country Acres with beautiful view in every direction

Sleeps 14 · 3 bedrooms · 2+ bathrooms

for 3 nights, 1 home

AU$360 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Madison County

Holliwell Bridge Retreat - Private, Spacious & Close to town! Great for Groups!

Charming 1855 Stone Farmhouse Retreat – Cozy Stays & Picturesque Views Await

Sleeps 12…. 5 beds and a sofa sleeper. 20 min from West Des Moines..

Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

Charming Winterset Vacation Rental w/ Yard & Patio

Serenity Heights - Peaceful Country Acres with beautiful view in every direction

Find spaces that suit your style

Family-friendly Rentals in Madison County

Holiday Rental options in Madison County