Snowmass which includes snow, snow skiing and a gondola

Pitkin County rentals with pool

We found 1,716 rentals with pool — enter your dates for availability

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September 2025

October 2025

Explore Pitkin County rentals with pools

Premier Host

Historic Cottage on Private Estate with Swimming Pool & Tennis Court on Site!

Sleeps 4 · 1 bedroom · 1 bathroom

Luxury Estate w- Pool/Spa, 6 Miles To Town, Featured In Dwell Magazine

Sleeps 11 · 5 bedrooms · 5+ bathrooms

WALK to Lift NO Car Needed NO Owner Service Fee 100% cancellation REFUND option*

Sleeps 6 · 3 bedrooms · 3 bathrooms

Top rated rentals with pools - Pitkin County

Premier Host

Comfortable,Clean & Cozy

A great experience from start to finish .Our host was very responsive & apartment had everything we needed & more .Comfy beds , well equipped kitchen , steam shower .Everything was perfect .

Mark F.

Stayed Feb 2025

Awesome Property and Location

Our holiday here was an excellent experience from beginning to end. Tami is a superb host, very reliable, quick to respond and accommodating. The flexibility and ability to respond to our changing needs was very much appreciated. Will definitely book again through Tami in future.

Daniel B.

Stayed Jan 2022