The weather is turning, and usually this is the time of year real estate agents say their business is slowing down. But, for investor agents in Denver, it’s the time of year our phone starts ringing with people wanting to buy mountain homes to enjoy themselves and rent on Airbnb the rest of the year.
There are a lot of reasons why this is a good play – you could have a vacation home that costs you nothing, you could have a cash cow if you operate a professional short term rental or you could do a cost seg with accelerated depreciation and reduce your taxable income drastically.
If any of the above benefits of buying a STR in the mountains appeals to you, then read on, we’ll tell you where to buy, strategies to consider and most importantly cautionary tales to make sure you’re purchasing the right thing.
First stop: Fairplay
Fairplay can be an appealing alternative for investors who want access to Colorado’s mountain economy without paying Summit County prices. The town is approximately 23 miles from Breckenridge and attracts visitors interested in skiing, hiking, fishing, hunting and exploring South Park, or South America if you’re following the spoof.
The Town of Fairplay has established a limited number of short-term rental permits, check out Fairplay’s current STR information. Licenses become available if another one is surrendered. Be sure the property you’re looking at is actually in town limits and do not fall under Park County’s jurisdiction instead.
Why investors should look here: Relative affordability, proximity to Summit County and demand from multiple types of outdoor recreation.
What to verify: Current permit availability, town versus county jurisdiction, well and septic requirements, fire inspection standards and HOA restrictions.
Next up: Leadville
Leadville offers access to skiing, hiking, mountain biking, fishing and Colorado’s highest peaks. Its year-round recreational demand and comparatively approachable purchase prices make it worth considering as an alternative to larger resort communities.
There are different licenses for owner-occupied or non-owner occupied licenses, check out the fees and annual application process here Review Leadville’s STR program.
Why investors should look here: Four-season recreation, access to Ski Cooper and proximity to Copper Mountain, while generally offering a lower entry price than major ski resorts.
What to verify: License classification, availability, transfer rules, occupancy limits, inspections and whether the property falls inside the City of Leadville or unincorporated Lake County.
Over to Winter Park
Winter Park is one of the more established vacation-rental markets on this list. It benefits from ski traffic during the winter and hiking, biking, festivals and other activities during the warmer months.
Short-term rentals are permitted, but every property must be registered before it is advertised or rented. Owners must display the registration number in advertisements, renew their registration annually and complete required fire and life-safety steps. Review Winter Park’s registration requirements.
Why investors should look here: Recognizable destination, strong ski demand and meaningful summer tourism.
What to verify: Registration eligibility, annual inspection requirements, HOA rules, dues, special assessments, parking and realistic seasonal occupancy.
Finally, make sure you don’t miss Pagosa Springs
Pagosa Springs has several sources of visitor demand, including its hot springs, proximity to Wolf Creek Ski Area, fishing, hiking and year-round outdoor recreation. The diversification can make it less dependent on a single tourism season. Which is good considering the poor snow conditions of recent winters.
Pagosa Springs is geographically farther from Denver than many Front Range mountain markets, but that distance may create an opportunity for investors willing to learn a more destination-driven market. Review Pagosa Springs’ vacation-rental requirements.
Why investors should look here: Hot springs, skiing and summer recreation create multiple reasons to visit throughout the year.
What to verify: Town versus county jurisdiction, license requirements, taxes, water and sewer service, property-management availability and HOA restrictions.
What Does “STR-Friendly” Really Mean?
An STR-friendly town is not necessarily one with no regulations. Clear, predictable regulations can be better for investors than a market with unclear rules that could change suddenly.
A strong STR market should offer a reasonable combination of:
- A defined path to obtaining a license
- Licenses available to non-owner-occupied properties
- Year-round or diversified visitor demand
- Purchase prices supported by realistic revenue
- Access to cleaners, contractors and property managers
- Regulations that allow the property to operate at a practical occupancy
- A viable backup plan if STR rules or travel demand change
The best investment is not always the property with the highest projected Airbnb revenue. It may be the property that produces slightly less revenue but has lower operating costs, clearer regulations and the ability to transition into a mid-term or long-term rental. Download The FI Team’s STR investment calculator to crunch the numbers.
If you need help analyzing a deal, determining estimated rents, occupancy, fees, etc. then reach out to be connected to an agent who specializes in this market.
What to Verify Before Making an Offer
Before purchasing any property with plans to use it as an STR, investigate:
- Exact jurisdiction: Is it governed by the town, the county or both?
- Current license availability: Is the town accepting applications, capped or operating a waitlist?
- Transferability: Does an existing license remain after the property is sold?
- Zoning: Is the property located in an area where STRs are permitted?
- HOA restrictions: An HOA may prohibit STRs even when the town allows them.
- Occupancy and parking: These rules directly affect revenue potential.
- Taxes and fees: Include lodging taxes, sales taxes, license fees and inspection costs.
- Insurance: Confirm that appropriate STR coverage is available and affordable.
- Seasonality: Underwrite slow months, not just holiday and ski-season rates.
- Backup strategy: Determine what the property could earn as a mid-term or long-term rental.
Considering a Colorado mountain property? The FI Team can help you evaluate the location, licensing requirements, rental potential and backup strategy before you make an offer. Let us know what you’re looking for and we’ll help you navigate the process.
Short-term rental regulations change frequently. This article is educational and reflects information available in September 2026. Buyers should independently confirm all requirements with the applicable municipality, county, HOA, attorney and tax professional before purchasing or operating an STR.
