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The highest-performing listings in Fairplay.
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Challenging to Investors
STRs are legal in Fairplay but capped at 20 permits (half already issued), with no waitlist and first-come, first-served allocation—meaning entry is constrained by limited supply. Permitting involves multiple steps (owner-only application, safety/inspection, business license, taxes), moderate fees, and ongoing compliance, which is manageable but not trivial. Outside town on well/septic, Park County’s regime is even more burdensome with a $605 fee, extensive documentation, and mandatory plans/inspections, increasing investor risk.
Local STR Agent
STR specialist · Fairplay, CO
Fairplay is a small high-altitude town in Park County, Colorado, home to roughly 700 residents who live amid the wide-open grasslands of the South Park basin. The community has a quiet, frontier-era character, with a short historic Main Street, weathered brick storefronts, and views that sweep toward the snow-streaked Mosquito Range. Best known as the town that gave its name to the famous South Park region, Fairplay also serves as a popular staging ground for hikers, anglers, and fourteener baggers heading into the surrounding mountains. It sits about 85 miles southwest of Denver, typically a drive of just under two hours via US Highway 285, which makes it a workable weekend escape from the Front Range while still feeling genuinely off the beaten path.
Just south of town, South Park City is a 4-acre open-air museum of more than thirty restored historic buildings filled with artifacts from the 1880s through the 1920s. The museum preserves a slice of South Park's mining and ranching past, with a church, a schoolhouse, a saloon, and an assay office all arranged in a walkable village setting. From downtown Fairplay, it is roughly a minute or two by car, making it an easy anchor stop for visitors passing through.
To the north, the Mosquito Range rises sharply and holds several of Colorado's famous "fourteeners," including Mount Democrat, Mount Lincoln, and Mount Bross, all accessible from trailheads just 15 to 20 minutes from town. Climbers use Fairplay as a base for these alpine starts, often pairing an early-morning summit with lunch back in town. The range also offers lower-elevation hiking and fall aspen viewing that draws leaf-peepers in late September.
Larger outdoor experiences lie a short drive away at Eleven Mile State Park, about 25 miles northeast of Fairplay, where an 11-mile reservoir draws anglers, sailors, kayakers, and campers. The neighboring Spinney Mountain Reservoir adds another angling-focused getaway, and both areas sit within the broader South Park recreational region. A bit farther north, the ski resort and historic mining town of Breckenridge is reachable in roughly 35 to 45 minutes, opening up winter sports, shopping, and dining for guests who want a turnkey mountain-town day trip without committing to its higher lodging rates.
Together, these offerings make Fairplay a compelling base for short-term rentals. The town pairs small-town character and a noticeably lower cost of entry with quick access to alpine summits, blue-ribbon reservoirs, and one of Colorado's most visited ski destinations, giving owners a year-round calendar of guests drawn to high-country adventure.