What does Tailored Stays charge for STR management in Colorado?

Tailored Stays charges a percentage of gross rental revenue, which varies based on property type, location, and services required. We offer a free revenue projection consultation to model your specific property before you commit.

Which Colorado markets does Tailored Stays serve?

Tailored Stays manages premium short-term rentals across 8 Colorado markets: Denver Metro, Summit County (Breckenridge, Keystone, Frisco), Clear Creek County (Idaho Springs, Georgetown), Boulder & Foothills, Estes Park / Rocky Mountain National Park, Grand County (Winter Park, Grand Lake), Park County (Fairplay, South Park), and the Pikes Peak Region (Colorado Springs, Manitou Springs).

How much can a 3-bedroom Colorado mountain property earn on Airbnb?

Annual revenue for a well-managed 3-bedroom Colorado mountain property varies significantly by market. Summit County (Breckenridge area) properties typically earn the most due to dual ski and summer seasons. We provide free, property-specific revenue projections that model your exact location, bedroom count, and amenities.

Does Tailored Stays manage Airbnb and VRBO listings?

Yes. Tailored Stays manages listings across all major short-term rental platforms including Airbnb, VRBO, and direct booking channels. We optimize listing placement, pricing, and guest communication across all platforms.

How is Tailored Stays different from large STR management companies?

Tailored Stays is a boutique operation, not a franchise or large-scale management company. We accept a small number of new properties each season — not because of capacity, but because every owner, every guest, and every property in our portfolio deserves personal attention that cannot scale. Owners work directly with Anson Roberts, the founder.

What is Tailored Stays' average revenue lift compared to self-managed properties?

Tailored Stays 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.

Does Tailored Stays offer a revenue guarantee?

Yes. Tailored Stays offers 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.

Owner Intelligence

Colorado STR intelligence, from the field.

Practical guides on revenue strategy, market analysis, regulations, and investment analysis — written for owners with 1–6 properties who want to think like operators.

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Start Here — Owner's Guide

Colorado STR Management in 2026: An Owner's Start Here Guide

Everything a Colorado property owner needs to know about short-term rental management in 2026 — from choosing …

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Breckenridge Airbnb Income Guide 2026: What Owners Actually Make in Colorado

Unlock the true earning potential of your Breckenridge, Colorado Airbnb or VRBO. This guide breaks down realistic income by bedroom count, seasonality, and the strategies top performers use to maximize revenue.

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Complete Collection

Colorado STR Income Guides: All 7 Markets in One Place

Breckenridge · Estes Park · Winter Park · Clear Creek · Park County · Pikes Peak · Denver Metro

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Mastering Colorado's STR Shoulder Seasons: Spring & Fall Revenue Strategies

Revenue Strategy

6 min readSeptember 2024

Mastering Colorado's STR Shoulder Seasons: Spring & Fall Revenue Strategies

Discover how top Colorado short-term rental operators leverage dynamic pricing, strategic property preparation, and targeted marke...

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10 Questions Every Colorado STR Owner Should Ask Before Signing a Management Contract

Operations

7 min readOctober 2024

10 Questions Every Colorado STR Owner Should Ask Before Signing a Management Contract

Navigate the complexities of short-term rental management in Colorado by asking these 10 crucial questions before partnering with ...

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The Amenity Arms Race: Which Upgrades Deliver the Highest ROI?

Revenue Strategy

6 min readNovember 2024

The Amenity Arms Race: Which Upgrades Deliver the Highest ROI?

Hot tubs, EV chargers, game rooms, ski lockers — not all amenity investments are equal. Here's what the data says about which upgr...

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Clear Creek County STR Investing in 2026: The Underrated Colorado Market Close to Denver

Market Analysis

9 min readMarch 3, 2026Updated 2026

Clear Creek County STR Investing in 2026: The Underrated Colorado Market Close to Denver

While Breckenridge and Summit County dominate the headlines, Clear Creek County quietly delivers some of the strongest risk-adjust...

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5 Costly Self-Managing Colorado STR Mistakes That Are Eating Your Profits

Owner Strategy

12 min readMarch 2026Updated 2026

5 Costly Self-Managing Colorado STR Mistakes That Are Eating Your Profits

Discover the five most common and costly mistakes self-managing Colorado STR owners make, and how these errors erode profits and i...

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How to Get More 5-Star Reviews on Airbnb & VRBO: A Colorado STR Owner's Guide

Guest Experience

7 min readMarch 2026Updated 2026

How to Get More 5-Star Reviews on Airbnb & VRBO: A Colorado STR Owner's Guide

Your review rating is the most important factor in your listing's search ranking and booking conversion rate. Here's the systemati...

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Investment

11 min readMarch 2026Updated 2026

Is Breckenridge a Good STR Investment in 2026? An Honest Market Analysis

Breckenridge commands some of the highest STR ADRs in Colorado — but is it still a smart investment in 2026? We break down the rea...

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Investment

10 min readMarch 2026Updated 2026

Buying a Colorado STR Investment Property: The 8-Point Due Diligence Checklist

Buying a short-term rental in Colorado is different from buying a long-term rental or a primary residence. Here's the due diligenc...

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Colorado Springs & Pikes Peak STR Investing in 2026: The Underrated Front Range Market

Investment

8 min readMarch 2026Updated 2026

Colorado Springs & Pikes Peak STR Investing in 2026: The Underrated Front Range Market

Colorado Springs is one of the most underrated STR markets in the state — a city of 500,000 with year-round tourism anchored by Pi...

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Colorado STR Management in 2026: An Owner's Start Here Guide

Investment

12 min readMarch 2026Updated 2026

Colorado STR Management in 2026: An Owner's Start Here Guide

Everything a Colorado property owner needs to know about short-term rental management in 2026 — from choosing a manager to underst...

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Colorado STR Market Outlook 2026: Regional Trends & What They Mean for Owners

Market Intelligence

8 min readMarch 2026Updated 2026

Colorado STR Market Outlook 2026: Regional Trends & What They Mean for Owners

Navigate the dynamic 2026 Colorado STR market with insights into demand, supply, and economic factors across Summit County, Clear ...

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Regulations

8 min readMarch 2026Updated 2026

Colorado STR Regulations in 2026: A Market-by-Market Guide for Property Owners

Short-term rental regulations in Colorado vary dramatically by city and county — and they change frequently. This guide covers the...

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Denver Metro STR Investing in 2026: The Urban and Suburban Opportunity Most Investors Overlook

Investment

9 min readMarch 2026Updated 2026

Denver Metro STR Investing in 2026: The Urban and Suburban Opportunity Most Investors Overlook

Denver Metro doesn't have ski lifts or a national park at its doorstep — but it has something arguably more valuable for STR inves...

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How Much Can You Earn From a Short-Term Rental in Denver in 2026?

Investment

9 min readMarch 2026Updated 2026

How Much Can You Earn From a Short-Term Rental in Denver in 2026?

Real revenue data, neighborhood-by-neighborhood breakdowns, and the honest truth about what separates a $25k/year Denver STR from ...

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What Dynamic Pricing Actually Does to Your Colorado Vacation Rental Revenue (Real Numbers)

Revenue Strategy

9 min readMarch 2026Updated 2026

What Dynamic Pricing Actually Does to Your Colorado Vacation Rental Revenue (Real Numbers)

Three Colorado STR case studies: Summit County +111% revenue, Denver Metro +53%, Winter Park occupancy 48→71%. Here's exactly what...

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Investment

10 min readMarch 2026Updated 2026

Is Estes Park a Good STR Investment in 2026? Rocky Mountain Gateway Market Analysis

Estes Park sits at the entrance to Rocky Mountain National Park — one of the most visited national parks in the country. But does ...

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Estes Park STR Regulations Explained: What Every Property Owner Needs to Know Before Listing

Regulations & Tax

8 min readMarch 2026Updated 2026

Estes Park STR Regulations Explained: What Every Property Owner Needs to Know Before Listing

Estes Park and Larimer County have separate, overlapping STR licensing requirements that catch many owners off guard. This guide e...

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Self-Managing vs. Evolve vs. Boutique Management: Which Model Makes Colorado Owners More Money?

Operations

10 min readMarch 2026Updated 2026

Self-Managing vs. Evolve vs. Boutique Management: Which Model Makes Colorado Owners More Money?

A straight-talking comparison of self-managing, using Evolve, and hiring a boutique Colorado property manager. Real numbers, real ...

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Grand County STR Investing in 2026: Winter Park, Granby & Grand Lake Market Analysis

Investment

9 min readMarch 2026Updated 2026

Grand County STR Investing in 2026: Winter Park, Granby & Grand Lake Market Analysis

Grand County offers a compelling alternative to Summit County's premium prices — with Winter Park Resort, Rocky Mountain National ...

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Regulations

6 min readMarch 2026Updated 2026

Clear Creek County STR Regulations in 2026: What Changed and What Owners Need to Know

Clear Creek County overhauled its STR administrative framework in late 2025 and increased license fees significantly in 2026. Here...

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Regulations

6 min readMarch 2026Updated 2026

Denver STR Regulations in 2026: The Primary Residence Rule and What It Means for Owners

Denver's primary residence requirement is the most important regulatory constraint for STR investors in the city. Here's what it m...

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Regulations

6 min readMarch 2026Updated 2026

Estes Park & Larimer County STR Regulations in 2026: Vacation Home Licensing Guide

Estes Park and Larimer County use a Vacation Home License framework for short-term rentals. Here's what's required, what's changed...

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Regulations

7 min readMarch 2026Updated 2026

STR Regulations in Summit County & Breckenridge (2026): What Property Owners Need to Know

Summit County and the Town of Breckenridge have some of the most complex STR licensing frameworks in Colorado — including license ...

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Summit County vs Estes Park STR Investment Colorado: Where Should You Put Your Money?

Market Insights

10 min readMarch 2026Updated 2026

Summit County vs Estes Park STR Investment Colorado: Where Should You Put Your Money?

A direct, data-driven comparison of Summit County and Estes Park for STR investors. We cover entry price, revenue potential, seaso...

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How to Earn Revenue Year-Round From Your Colorado Mountain STR

Revenue Strategy

8 min readMarch 2026Updated 2026

How to Earn Revenue Year-Round From Your Colorado Mountain STR

Most Colorado mountain STR owners leave 30–40% of their annual revenue potential on the table by failing to capture shoulder seaso...

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Guest Experience

9 min readJune 2024

Crafting 5-Star Stays: Guest Experience Design for Colorado Mountain STRs

Transforming your Colorado mountain short-term rental into a beacon of hospitality requires more than stunning views — it demands ...

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Investment

8 min readJuly 2024

How to Underwrite a Colorado STR Investment Using AirDNA and Rabbu

Learn how to leverage the power of AirDNA and Rabbu to underwrite your next Colorado short-term rental investment with confidence ...

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Colorado STR Regulations 2026: What Every Owner Needs to Know

Regulations & Tax

9 min readJanuary 2026Updated 2026

Colorado STR Regulations 2026: What Every Owner Needs to Know

Navigate the complex web of Colorado's county-specific short-term rental regulations, from permits and taxes to local rules, to en...

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The ROI of Professional Photography for Colorado STRs

Revenue Strategy

5 min readJanuary 2026Updated 2026

The ROI of Professional Photography for Colorado STRs

Discover how professional photography can significantly boost bookings, average daily rates, and overall revenue for your Colorado...

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Summit County vs. Denver Metro: Which STR Market Delivers Better Returns?

Investment

8 min readDecember 2024

Summit County vs. Denver Metro: Which STR Market Delivers Better Returns?

For short-term rental investors in Colorado, the choice between Summit County's high ADRs and Denver Metro's stable occupancy pres...

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The Hidden Costs of Self-Managing Your Colorado Vacation Rental

Operations

7 min readAugust 2024

The Hidden Costs of Self-Managing Your Colorado Vacation Rental

Uncover the often-overlooked financial and personal costs of self-managing your Colorado vacation rental and learn when profession...

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Clear Creek County Airbnb Income Guide 2026: What Owners Actually Make 45 Minutes from Denver

Market Insights

7 min readApril 2026Updated 2026

Clear Creek County Airbnb Income Guide 2026: What Owners Actually Make 45 Minutes from Denver

Clear Creek County is Colorado's most accessible mountain STR market — 45 minutes from Denver on I-70, with Idaho Springs at its c...

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Estes Park Airbnb Income Guide 2026: What Owners Actually Make at the Gateway to Rocky Mountain National Park

Owner Strategy

6 min readApril 2026Updated 2026

Estes Park Airbnb Income Guide 2026: What Owners Actually Make at the Gateway to Rocky Mountain National Park

Discover the true earning potential of your Estes Park, Colorado Airbnb or VRBO. This guide breaks down realistic income by bedroo...

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How to Choose a Colorado STR Property Manager (Without Getting Burned)

Management

7 min readApril 2026Updated 2026

How to Choose a Colorado STR Property Manager (Without Getting Burned)

Most Colorado STR owners who switch property managers say the same thing: they wish they'd asked these questions before signing. H...

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Winter Park Airbnb Income Guide 2026: What Owners Actually Make in Colorado's Dual-Season Mountain Market

Owner Strategy

7 min readApril 2026Updated 2026

Winter Park Airbnb Income Guide 2026: What Owners Actually Make in Colorado's Dual-Season Mountain Market

Discover the true earning potential of your Winter Park, Colorado Airbnb or VRBO. This guide breaks down realistic income by bedro...

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Colorado STR Tax Strategies: What Your CPA Might Be Missing

Regulations & Tax

8 min readApril 2024

Colorado STR Tax Strategies: What Your CPA Might Be Missing

Unlock significant tax savings for your Colorado short-term rental investment by mastering depreciation, the Augusta Rule, and oth...

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Park County / Fairplay Airbnb Income Guide 2026: What Colorado's Most Affordable Mountain Market Actually Pays

Market Data

7 min readApril 2, 2026Updated 2026

Park County / Fairplay Airbnb Income Guide 2026: What Colorado's Most Affordable Mountain Market Actually Pays

Park County sits 90 minutes from Denver with median home prices well below Breckenridge—yet a 6-bedroom cabin here can gross $141,...

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Colorado STR Income Guides: How Much Can You Actually Make?

Market Intelligence

3 min2026-04-02Updated 2026

Colorado STR Income Guides: How Much Can You Actually Make?

Complete income guides for Colorado's top STR markets — Breckenridge, Estes Park, Winter Park, Clear Creek County, Park County, an...

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Pikes Peak Area Airbnb Income Guide 2026: How Much Can You Actually Make?

Market Intelligence

7 min2026-04-02Updated 2026

Pikes Peak Area Airbnb Income Guide 2026: How Much Can You Actually Make?

Real revenue data for the Pikes Peak area STR market — from Cripple Creek to unincorporated Teller County. Bedroom breakdowns, sea...

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Insights

5 min read

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