Last reviewed October 14, 2026.
A lot of my buyers want a place in Aspen that pays for part of itself. Some want a ski condo they can use a few weeks a year and rent the rest. Others are trading up from a rental somewhere else.
Both can work. But an Aspen rental is not a typical rental. The permit rules, the HOA rules and the taxes shape what a property can earn. Two condos on the same block can have very different rental futures.
Here's how I walk investors through it. Every rule, fee and tax below links to its official source, and I checked each one on October 14, 2026. Rules here change often, so treat this as a map, not advice for your specific deal.
Before we look at a single listing, I ask one question. How do you plan to rent it?
Short-term (less than 30 days). In the City of Aspen, any stay under 30 days is a short-term rental (STR). You need a City STR permit and a business license before your first guest arrives. [1]
Long-term (30 days or more). Monthly, seasonal and annual leases don't need a City STR permit. They do need a City business license. [1][2]
A mix of both. Many of my owners do a winter season lease, a few summer months, and keep some weeks for themselves.
Here's why the answer matters. A property with no realistic path to an STR permit can still be a fine long-term rental. But you should price it, and plan your income, as a long-term rental. In my experience, the gap between the two can be big.
One more thing to decide early: how much will you use it yourself? It matters for your taxes.
Buying through a 1031 exchange? Many of my investor buyers sell property elsewhere and buy in Aspen through a 1031 exchange, which can defer tax on the gain. The IRS deadlines are strict, and Aspen inventory that fits an investor's list is thin, so start looking before you sell. I cover the rules and what I've learned in my Aspen 1031 exchange guide.
This is the first filter I run on any address.
The rules are very different. In unincorporated Pitkin County, for example, STRs have a 4-night minimum and a 120-night yearly maximum. The property must also show a history of short-term rental use between May 11, 2017 and May 11, 2022. [3] So many county homes simply can't get a license.
Not sure which side of the line a home is on? The City has a map that shows whether an address is in or out of Aspen. [1]
Inside the city, the zone district drives your STR options. The City offers three permit types. [1]
Capped vs. uncapped zones. Classic permits are capped in zones such as R/MF, R-6, R-15 and Mixed Use. There's no cap in the Commercial (C-1), Commercial Core (CC), Lodge (L), Commercial Lodge (CL), Lodge Overlay and Lodge Preservation Overlay zones. [1] That's why "lodge zone" shows up on so many investor wish lists, including the search criteria I send out to other brokers.
A lodge zone doesn't automatically mean lodge rules, though. A property in the L zone has to meet the City's definition of a "lodge" to qualify for a Lodging Exempt permit. [1]
How the waitlist works. When a capped zone is full, new Classic applications go on a waitlist in the order they were received. You pay the non-refundable $394 permit fee to hold your place. If a permit opens up, you have 14 days to accept it. [1] The City says wait times are hard to predict. [2]
Before an offer, I pull the address on the City's STR map and check the Classic permit availability summary. [1]
The permit doesn't come with the home. In the City of Aspen, an STR permit ends when the property sells. The new owner applies for a new one. [5] Since late 2025, a temporary permit can let a new owner honor limited reservations booked before the sale. [6] So "it has a permit" in a listing tells you the history, not your future. I cover all of this in more detail in my STR permit guide.
Most Aspen investment properties are condos or townhomes. That means an HOA, and HOA rules can override what the City would allow.
When I search for investors, I look for two things together: STR permit availability, and no (or minimal) HOA restrictions on short-term rentals. Here's what I've learned to watch for:
Colorado's standard purchase contract gives buyers a deadline to receive and review association documents, and the right to object to them. [7] Use that time. Read the declarations, bylaws and rules and regulations. If something about rentals is unclear, ask the HOA in writing.
Good to know: in late 2025, the City stopped requiring HOA affidavits at STR permit renewal. [6] That doesn't change your HOA's rules. You still have to follow them.
This is where I see the most wishful thinking. Here's how I build real numbers.
Start with actual history, not a pro forma. Ask the seller for rental statements and tax filings. Then call the property manager. Ask what the unit has actually earned, what a healthy range looks like, and what it has never reached. In one search, a listing agent was candid that a unit had never hit the top number people were floating. That one call reset the whole offer.
Look at real rental comps. Compare similar units in similar buildings, and note whether each figure is a monthly lease or a nightly total. Those two numbers aren't apples to apples.
Subtract the taxes guests pay, and file them. Aspen adds a short-term rental tax on top of sales and lodging taxes. The STR tax is 10% for Classic properties and 5% for Owner-Occupied and Lodging Exempt properties. The City lists the 2026 total tax on a nightly Classic STR stay at 22.35%. [8] Guests pay these taxes, but they raise the all-in price of your rental compared with a hotel. You file them with the City every month, even in months with no bookings. [1][8]
Count every fee. In the city: the $394 yearly Classic permit and the $150 yearly business license. [1] In the county, the license fee is a percentage of the Assessor's market value: 0.05% for 20 nights or fewer, 0.06% for 21 to 60 nights, and 0.07% for 61 to 120 nights. [3]
Count the carrying costs. HOA dues, insurance, property taxes, utilities, management, cleaning and repairs. Plus months the unit sits empty. From my own experience owning a rental here, the costs don't take a month off when the rent does. Budget for vacancy.
Property taxes. Pitkin County sets the value, and Colorado's assessment rates and the local mill levies set the bill. [9] I break it down in my property tax guide.
Keep the permit alive. A City STR permit needs at least one short-term stay a year, shown in your tax filings, to renew. A year of zero filings means the City treats the permit as abandoned. Long-term stays don't count. [1]
About cap rates. Investors often ask me for "the Aspen cap rate." I don't quote one. It varies a lot by building, permit status and how you rent. Run the numbers on the specific unit.
On top of the normal home inspection, here's what I want buyers to see before their deadlines pass:
Aspen guests expect hotel-level service. Unless you live here, you'll want local help.
I love helping investors find the right fit. Before you write an offer, I'll help you check the permit path, read the HOA rules, pressure-test the rental numbers and line up your timing if you're selling another property first. I'll also reach out to my broker network for options that aren't on the market yet.
Start with how I work with buyers.
Often, but not always. Inside city limits you need a City STR permit and a business license. Investors usually need a Classic permit, which is capped in many residential zones and may have a waitlist. Your HOA can also restrict or ban short-term rentals.
No. In the City of Aspen, an STR permit ends when the property sells, and the new owner must apply for a new one. Since late 2025, a temporary permit can let a new owner honor limited reservations booked before closing.
The City lists no cap in the Commercial (C-1), Commercial Core (CC), Lodge (L), Commercial Lodge (CL), Lodge Overlay and Lodge Preservation Overlay zones. Many residential zones are capped.
Aspen adds a short-term rental tax on top of sales and lodging taxes: 10% for Classic properties and 5% for Owner-Occupied and Lodging Exempt properties. The City lists the 2026 total on a nightly Classic STR stay at 22.35%. Owners file monthly with the City.
Only with a county STR license. Rentals need a 4-night minimum, are limited to 120 nights a year, and the property must show short-term rental history between May 11, 2017 and May 11, 2022.
This guide is general information, not legal, tax or investment advice. Rules, fees and taxes change. Confirm everything with the City of Aspen, Pitkin County, and your own attorney and tax advisor before you buy.
Katherine Coleman, Broker Associate | The Agency Aspen | Own In Aspen
205 S. Mill Street, Suite 110, Aspen, CO 81611 | owninaspen.com | CO License FA.100088194
Each office is independently owned and operated.