Big Sky Resort featuring horseriding, tranquil scenes and land animals

Madison County rentals with pool

We found 230 rentals with pool — enter your dates for availability

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December 2025

11

January 2026

Explore Madison County rentals with pools

The Great Room

Premier Host

Premier Mountain Home Includes Private Lodge with Pool & Ski in/out Access

Sleeps 10 · 4 bedrooms · 3+ bathrooms

The Great Room with commanding views and beautiful stone fire place

Premier Host

Stunning 5 Bedroom 5.5 Bath Home, Private Hot Tub, Ski in/out, & Lodge Access

Sleeps 12 · 5 bedrooms · 5+ bathrooms

Interior

Premier Host

Lone Peak Views - 6 bedroom 6.5 bath, ski in/out, Private Hot Tub, Lodge Access

Sleeps 16 · 6 bedrooms · 6+ bathrooms

Private kitchen

Main House – Restored Historic Log Cabin, known as the Ennis Homestead

Sleeps 6 · 3 bedrooms · 2 bathrooms

Dining

Premier Host

Magnificent Mountain Views, 6 Bedroom 6.5 Bath, Private Lodge, Ski in/out

Sleeps 14 · 6 bedrooms · 6+ bathrooms

Find spaces that suit your style

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Condo/Apartment

Rentals with Pool in Madison County

Holiday Rental options in Madison County

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