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Built for owners who want results, not excuses.
We work with a small, carefully selected portfolio of premium Colorado properties — mountain retreats and Front Range homes alike. Not every property is a fit — and that's intentional.
New to short-term rentals?
Let's build a plan together — from market selection to first booking.
Book a Free STR Strategy CallAlready hosting but not seeing the returns?
We'll audit your current setup and show you exactly where revenue is being left on the table.
Three promises. Every property. Every time.
Maximum revenue, minimum vacancy.
Dynamic pricing algorithms, multi-platform distribution, and listing optimization that consistently outperform self-managed properties by 40–80%.
Your property treated like our own.
Vetted cleaning teams, preventive maintenance, professional photography, and a property inspection after every single stay.
You're never left wondering.
Monthly owner statements, real-time booking notifications, and a local team that responds — not a call center or ticketing system.
Colorado's finest mountain and urban corridors.
Two paths to the same goal.
Whether you own a property or are evaluating one, we have a service built for you.
Owner-friendly terms. No surprises.
No long-term contracts
Straightforward, owner-friendly agreements. We earn your trust every month — not just at signing.
Transparent fees
Clear percentage of gross revenue. No hidden charges, no surprise line items on your monthly statement.
Candid about fit
If your property isn't a fit for our model, we'll tell you honestly — and point you toward other local options when we can.
Owner portal access
Real-time booking visibility, owner block management, and monthly performance reports — always on.
Real owners. Real results.
“I honestly didn't think the property could do much better. Anson showed me exactly where I was leaving money on the table — and then went and fixed it.”
“The event pricing alone paid for the management fee several times over. I had no idea how much I was leaving on the table during Broncos weekends.”
“Summer was always our weak spot. Anson turned it into almost as strong a season as winter — I didn't think that was possible in Winter Park.”
Properties we manage in Colorado.
Every property in our portfolio is actively managed — not just listed. Browse our current Colorado inventory on Airbnb.
These properties average 4.88 stars across 829 reviews — all under Tailored Stays management.
View all listings on Airbnb"Wow, is all I can say about Tailored Stays. Anson is a wealth of knowledge and information about his market and short term rentals in general. He was very helpful in guiding me to achieve my goals. I would highly recommend Tailored Stays for all of your STR needs."
"Anson and the rest of the Tailored Stays team are simply best in class. Their knowledge, attention to detail and commitment to their project and clients is second to none in the area. I would highly recommend them for any of your short term rental needs."
"Anson and the team at Tailored Stays are superb. Excellent at what they do, truly professional hosts who treat guests and their host clients with respect and appreciation. Their efficient systems make for easy communications. Certainly also helps that Anson is a great guy! Highly recommend them!"
Built on a simple belief.
Tailored Stays was built on a simple frustration: the gap between what Colorado properties could earn and what most management companies actually delivered. Most companies compete on volume. We compete on outcomes.
We're intentionally small — our team knows every property by name, every quirk, and exactly which lever to pull when a market slows down. That's the standard we hold ourselves to, and it's non-negotiable.
Read Anson's full storyFrom conversation to cash flow in 3 weeks.
Free Revenue Projection
We analyze your property and build a realistic 12-month revenue model. No obligation.
Property Onboarding
Professional photography, listing creation, pricing setup, and platform accounts — often launched by us in 2–3 weeks.
Go Live & Optimize
Your property launches on Airbnb, VRBO, etc. We monitor, adjust, and optimize continuously.
Monthly Owner Reports
Clear, transparent statements every month. Direct deposit to your account. No surprises.
We're not for everyone. Intentionally.
Great Fit For Owners Who:
Probably Not a Fit For Owners Who:
Questions we hear most.
We charge a management fee as a percentage of gross revenue — typically 20–25% depending on the property and services required. No hidden fees.
Not at all. We handle everything — guest communication, cleaning coordination, pricing, maintenance, and reporting. You simply receive your monthly owner statement and direct deposit.
Most properties are live on all platforms within 2–3 weeks of signing. We handle photography, listing creation, pricing setup, and all platform accounts.
We focus on premium Colorado properties within approximately 2.5 hours of Denver — Summit County, Clear Creek County, Grand County, Estes Park, Boulder Foothills, Park County, Pikes Peak, and Denver Metro. We also manage select properties in Crystal Beach, TX.
Absolutely. Owner blocks are easy to set. You'll have full access to the owner portal to manage your calendar and block any dates that you need.
Our owners typically see 30–80% more annual revenue compared to self-managed properties. The lift comes from dynamic pricing, professional photography, multi-platform distribution, and proactive guest communication — all working together.
Yes. We offer a 90-day revenue guarantee on qualifying properties. If we don't outperform your baseline in the first 90 days, we'll refund our management fee for that period. Ask us for details when you request your free revenue projection.
About Tailored Stays
Tailored Stays is a boutique vacation rental management company based in Colorado, founded in 2020 by Anson Roberts. The company manages a carefully selected portfolio of short-term rental properties across 8+ Colorado markets — including Denver Metro, Breckenridge and Summit County, Estes Park, Idaho Springs and Clear Creek County, Winter Park and Grand County, Fairplay and Park County, Colorado Springs and the Pikes Peak Region, and Boulder and the Foothills — as well as Crystal Beach, Texas.
Tailored Stays provides full-service short-term rental management for property owners, including dynamic pricing, professional listing optimization on Airbnb and VRBO, 24/7 guest communication, post-stay property inspections, and monthly owner reporting. The company charges a percentage-based management fee with no setup fees or hidden charges.
Guests can book Tailored Stays properties directly at book.tailoredstays.co with no platform fees, or through Airbnb and VRBO. Property owners interested in management services can request a free revenue projection at tailoredstays.co or by calling (303) 626-8499 for Colorado properties or (409) 812-2022 for Texas properties.