Rent Pitkin County Homes with Swimming Pools

We selected the 36 homes worth renting in this location

Home spotlights in Pitkin County

Two Pine Cones

Two Pine Cones

  • 10 guests

  • 4 bedrooms

Aspen, Pitkin County

This homey condo is located in a quieter spot but still within easy reach of downtown Aspen and all four local ski mountains on the handy free shuttle. While it sports a clean and modern aesthetic, panelled walls, wooden beams and a wood-burning fireplace create a cosy atmosphere.

Slopeside Living

Slopeside Living

  • 6 guests

  • 3 bedrooms

Aspen, Pitkin County

Just two blocks from the Silver Queen Gondola, this deluxe home in Aspen is ideally situated for making the most of the slopes in winter, whether you choose to ski, snowboard or try one of the many other snow sports available in the area. Downtown Aspen itself is just a short distance away too, so the upmarket restaurant and boutiques are practically on your doorstep.

Buttercream Frosting

Buttercream Frosting

  • 8 guests

  • 3 bedrooms

Aspen, Pitkin County

A slope-side paradise, this beautiful home is the true definition of a ski-in, ski-out location. You’ll be right at the foot of Aspen Mountain (with the views to match) and the Shadow Mountain chair lift is next to your front door.

Durant Cowhide

Durant Cowhide

  • 6 guests

  • 3 bedrooms

Aspen, Pitkin County

This home offers the comfort of a modern apartment and the convenience of having extensive building amenities, as well as a top-notch concierge service from your host. The shared heated pool and hot tub are perfect for post-ski relaxation and meeting fellow residents.


We selected the top 3% holiday homes in Pitkin County Homes with Swimming Pools

Explore the 36 most perfect homes in our collection

View on map

Most popular homes in Pitkin County

Cast Iron Cosiness

Cast Iron Cosiness

  • 6 guests

  • 3 bedrooms

Aspen, Pitkin County

Quaking Aspen Tree

Quaking Aspen Tree

  • 8 guests

  • 3 bedrooms

Aspen, Pitkin County

The Modern Moose

The Modern Moose

  • 8 guests

  • 4 bedrooms

Aspen, Pitkin County

Roaring Fork

Roaring Fork

  • 4 guests

  • 2 bedrooms

Aspen, Pitkin County

Stripped Birch

Stripped Birch

  • 6 guests

  • 3 bedrooms

Aspen, Pitkin County

Sounds Of The Stream

Sounds Of The Stream

  • 6 guests

  • 2 bedrooms

Aspen, Pitkin County

Durant Basecamp

Durant Basecamp

  • 10 guests

  • 4 bedrooms

Aspen, Pitkin County

Vacation Station

Vacation Station

  • 8 guests

  • 3 bedrooms

Aspen, Pitkin County

View all


Frequently asked questions

You've certainly come to the right place if you are hoping to find one of the finest Holiday Homes with Swimming Pools in Pitkin County, Colorado, United States. Our exclusive collection consists solely of homes that have passed our thorough 150-step vetting process with flying colours, so you can book with true peace of mind, knowing that everything from decibel levels in the bedroom to a room's intangible atmosphere has been tested and approved. We don't list a huge number of homes one our site, just the right ones. Each property in our collection comes fully furnished and ready to welcome you, with a fully-equipped kitchen, essential bathroom toiletries, and all linen included. Contact our dedicated team of experts to find the perfect luxury Pitkin County Home to Rent with a Swimming Pool today, and set up a holiday to remember.

Search Our Collection