Colorado Short-Term Rental Association

COSTRA Members-Only Webinars with Key Data
2026-08-11 11:00 - 11:30 (America/Denver)
We are excited to announce COSTRA’s newest industry partner: Key Data. Key Data is an important connection for the short-term rental community with access to reservations and traveler data across the country.
Benefits for COSTRA Members
This 30-minute monthly webinar will offer current active members of COSTRA a peek behind the curtain into key performance indicators including reservations trends, traveler forecasts, and important datapoints that will help you enhance your short-term rental booking strategies.
Trends to Watch
Keep an eye out in these webinars for things like average daily rate, booking windows, average length of stay, and average spend.
How to Use the Data
During the webinar, we’ll talk about what these data points mean for your short-term rental and how you can use this information to be more strategic in your revenue management.
Meeting Format
These exclusive member webinars will be set up in meeting format – which means you’ll have the opportunity to engage and ask questions, live! Cameras on, mics ready (just hang out on mute until we get to the Q&A).

Semi-Annual State of the Industry Webinar
2026-07-23 11:00 - 12:00
The short-term rental industry continues to evolve—and staying informed has never been more important.
Join COSTRA and our valued partners for our semi-annual State of the Industry Webinar, where we’ll provide the latest updates on the issues shaping Colorado’s short-term rental landscape.
During this one-hour session, we’ll cover key topics including local ordinances, state legislation, upcoming elections, economic trends, and the launch of COSTRA’s new Small Donor Committee. Whether you’re a host, property manager, or industry partner, you’ll gain valuable insights into the current landscape and what it means for your business.
What you’ll gain:
-Updates on local ordinances affecting Colorado’s STR industry
-The latest on state legislation and COSTRA’s advocacy efforts
-Insights into upcoming elections and their impact on STRs
-Economic trends influencing the hospitality market
-An introduction to COSTRA’s Small Donor Committee and ways to get involved
The webinar also features live polling and an interactive Q&A session, giving you the opportunity to share your perspective and ask questions directly to COSTRA leadership.
Audience participation is welcomed and encouraged.
If you have questions you’d like us to address during the webinar, please send them in advance to hello@coloradostra.org, and we’ll add them to our discussion list.
Whether you’re a longtime member or new to the industry, this webinar is your opportunity to stay informed, engaged, and prepared for what’s ahead.

Picture Perfect STRs: Photography & Property Buying Tips
2026-06-25 10:00 - 11:00
Join COSTRA for a webinar focused on two key areas of STR success: marketing your property effectively and making smart investment decisions.
In this session, you’ll learn:
-How professional photography can help your listing stand out
-Tips for maximizing your vacation rental’s visual appeal
-What to look for when buying or selling an STR property
-Key factors that impact long-term property performance and value
Featured Speakers:
-Jon Kreye — Photographer specializing in vacation rental photography
-Becca Christeson — Real estate professional focused on STR properties
Whether you’re an experienced operator or exploring your next investment, this webinar will provide practical takeaways you can apply right away.
Register today!

Pikes Peak Short-Term Rental Alliance Launch Party
2026-05-18 15:30 - 16:30
If you’re an STR owner, operator, vendor, or real estate professional, this is your opportunity to be in the room with others who understand the space and are actively shaping its future.
What to expect:
-Connect with local STR operators and industry professionals
-Hear updates on local and statewide regulations
-Learn how PPSTRA is advocating for fair, practical STR policies

Details:
Pikes Peak STR Alliance Launch Party
May 18, 2026 | 5:30–6:30 PM
Renjoy Office | 102 W Colorado Ave, Colorado Springs, CO
-Free to attend
-Food & drinks provided
-Optional donation
RSVP to join us!

Summer Prep: Coverage You Can’t Skip
2026-04-22 13:00 - 14:00
Summer in Colorado means hiking trails, festival weekends, and travelers coming to enjoy everything the season has to offer. It’s also the right time to make sure your short-term rental is properly protected. Join COSTRA and guest speaker Nick Massey from Proper Insurance on Wednesday, April 22, at 1 PM MT for a focused conversation on what hosts and operators need to know right now.
We’ll cover the essentials of STR insurance, common coverage gaps, and how to ensure your policy keeps up with your business. Whether you’re reviewing your current plan or exploring options for the first time, this session will help you head into the season with clarity and confidence.
What you’ll learn:

What a comprehensive STR insurance policy should include
Common gaps in standard homeowners and platform coverage
How to evaluate if your current policy is enough
Key questions to ask your insurance provider
Practical steps to better protect your property and income

Register now to reserve your spot >>

COSTRA & The Five Stars of Guest Readiness
2026-01-22 12:00 - 13:00
A truly guest-ready home is the foundation of a standout guest experience—but what does “guest ready” really mean? Join COSTRA for our January webinar featuring Well & Good’s The Five Stars of Guest Readiness. Jonathan Wicks of Well & Good will walk through each “star,” sharing practical, repeatable strategies hosts can use to consistently deliver five-star stays. Plus, Airbnb will join the conversation with expert listing tips to help you optimize your listing and make 2026 your best hosting year yet.
RSVP HERE

Winter Warmup STR Policy Updates, Pro Tips & Seasonal Safety
2025-12-11 10:00 - 11:00
With the 2026 legislative session expected to bring significant challenges for STRs across the state, now is the time to get informed and stay connected. Expedia will provide a forward-looking legislative preview, offering insights into key issues, trends, and policy discussions likely to shape the coming year.
We’ll also shift from policy to practice with a quick, practical hosting tips segment—perfectly timed for the busy winter season. And in a special guest appearance, Justin Ford of Breezeway will join us for a concise overview of the most important winter safety considerations every Colorado STR operator should keep in mind.
This fast-paced, information-packed session is designed to strengthen our community, give hosts a clear sense of what’s coming, and equip you with the tools to navigate both winter and the policy “storm” on the horizon
RSVP HERE

Colorado STR Summit
2025-11-15 08:00 - 15:00 | Denver Police Protective Association and PPA Event Center, 2105 Decatur Street, Denver, 80211, United States
The Colorado STR Summit is the annual gathering of our state’s short-term rental community. Whether you’re a host, property manager, realtor, or investor, this is where you’ll connect with the people shaping the future of STRs in Colorado.
This year’s program brings together voices from across the industry — from platforms and tourism leaders to data experts, safety specialists, accessibility advocates, and local hosts. Together, we’ll dig into the trends, challenges, and opportunities that matter most for your business and our community.
✔️ Meet fellow hosts and professionals navigating the same questions you are
✔️ Gain timely insights you can put into practice right away
✔️ Recharge with good food, conversation, and a celebratory happy hour to close the day
Your ticket includes:
✔️ Full-day program + Happy Hour
✔️ Lunch + 1 drink ticket
Pricing:
– Early Bird (through Oct 15): $60
– General Admission (Oct 16–Nov 15): $75
– Bundle & Save: COSTRA Membership + Ticket = $125
Seats are limited and the Summit has sold out in past years — reserve your spot today.

Keep More of Your Paycheck: STR Tax Strategy for W2s
2025-09-19 12:00 - 13:00
Tired of watching your paycheck shrink every tax season while you’re stuck in the time-for-money cycle? Dr. Christina Moss was there too. As a burned-out healthcare professional and new mom, she discovered how W2 employees can use short-term rental investing to keep more of what they earn. You’ll learn the bonus depreciation strategy most employees never hear about and how to use it to slash your 2025 tax bill. Walk away with a step-by-step plan to buy and set up your first STR property before year-end, creating a path to financial freedom that actually fits your busy W2 schedule. Free to attend live, with recordings available exclusively to Mile High Hosts and COSTRA members.

Register to Attend >

Introducing COSTRA: The Future of STR Advocacy in Colorado
2025-09-09 12:00 - 13:00
Join us for “Introducing COSTRA: The Future of STR Advocacy in Colorado,” a live webinar bringing together industry leaders to explore the evolving short-term rental landscape. Gain a clear legislative overview, hear insights from a statewide panel of experts, and engage in a Q&A session to address your most pressing questions about advocacy, regulations, and the future of STRs in Colorado.
REGISTER NOW >>
