📍 Madison STR Operations

Keepers + Hostaway for Madison, WI STR Operators

Hostaway handles your workflow. Keepers handles your operations. Together, you run a smarter STR business in Madison, WI.

Book a Free Demo → Learn More
20+
Hours saved per week
4.9★
Avg inspection score
100%
Turnovers tracked
1
Platform for everything

Everything you need to run your STR portfolio in Madison

Built for STR operators who are done duct-taping their operations together. Keepers handles every piece of your business in one powerful platform.

🔄

Turnover Automation

Auto-schedule cleaners, inspectors, and restockers based on reservations — zero manual coordination.

🔧

Maintenance Tracking

Log, assign, and resolve maintenance issues fast. Keep your properties guest-ready at all times.

💬

Guest Communications

Automate check-in instructions, house rules, and follow-ups. Deliver a 5-star guest experience every time.

🛒

Pro Marketplace

Find, hire, and rate vetted local service pros. Build a reliable team without the headache.

📅

Reservation Control

Full visibility into every reservation across all your properties and channels — in one calendar.

🤖

AI Quality Assurance

AI-powered inspection checklists and photo verification ensure nothing slips through the cracks.

💰

Financials & Statements

Owner statements, expense tracking, and financial reporting — all automated and always accurate.

📊

Portfolio Health

Real-time dashboards showing occupancy, revenue, and operational health across your entire portfolio.

📣

Team Communications

Keep your whole team — cleaners, maintenance, managers — aligned with built-in messaging and task tracking.

Book a Free Demo →

See Keepers in Action

Watch how STR operators use Keepers to automate turnovers, manage maintenance, and scale their portfolios — all in one platform.

The Gaps Left by Using Hostaway Alone

  • Hostaway handles reservations, but your Madison team still coordinates turnovers, maintenance, and quality control through group texts — creating chaos and missed tasks.
  • There's no automated photo verification ensuring your Madison properties are guest-ready before check-in, meaning issues only surface when guests complain.
  • Maintenance requests, inventory gaps, and team communications in Madison fall through the cracks because Hostaway wasn't built to manage operations — only bookings.

Keepers Fills the Operations Gap That Hostaway Leaves Behind

While Hostaway manages your Madison reservations and revenue, Keepers automates everything that happens between bookings — cleaning scheduling, AI photo inspection, maintenance routing, team communications, and financial tracking — so your operation runs flawlessly without constant manual oversight.

What Keepers Adds to Your Hostaway Workflow

  • Automated Cleaning Schedules — Sync with Hostaway check-out times to auto-assign your Madison cleaners. No manual scheduling, no missed turnovers.
  • AI Photo Verification — Cleaners submit photos after each turnover. Keepers AI checks every room against your checklist before your Madison guests check in — catching issues before they become reviews.
  • Maintenance Tracking — Report, route, and resolve maintenance issues from cleaner to contractor with full visibility — so nothing falls through the cracks between Hostaway stays.
  • Team Messaging — Property-linked communications replace scattered group texts. Every message in Madison is tied to the right property and the right task.
  • Financial Reporting — Track cleaning costs, maintenance expenses, and operational spend across your Madison portfolio alongside your Hostaway revenue data.
  • Service Provider Marketplace — Find and book vetted cleaners and service providers in Madison directly through Keepers — no more scrambling to fill open shifts.

Built for STR Operators in Madison, WI

Madison STR operators using Hostaway for reservations consistently tell us the same thing: the platform is great for booking management, but operations still feel chaotic. Keepers was built to solve exactly that — giving Madison operators the operations layer that turns a well-booked portfolio into a well-run one.

Ready to Run a Smoother Operation in Madison?

Join Madison STR operators who use Keepers alongside Hostaway to automate turnovers, verify quality, and track maintenance — without adding headcount.

Ready to transform your STR operations?

Run your entire STR operation — maintenance, guest comms, financials, and portfolio health — all in one platform.

Book a Free Demo →

Frequently Asked Questions

How does Keepers work with Hostaway for Madison operators?
Keepers integrates with Hostaway to sync reservation data and automate the operations layer. When Hostaway records a checkout in Madison, Keepers auto-schedules the cleaning, notifies the cleaner, tracks task completion, and verifies the property is guest-ready before the next check-in.
Does Keepers replace Hostaway?
No — Keepers complements Hostaway, not replaces it. Hostaway handles reservations and guest communications while Keepers manages the operational side: cleaning automation, maintenance tracking, AI photo verification, team communications, and financial reporting for your Madison portfolio.
What problems does Keepers solve for Madison operators using Hostaway?
The most common issues Madison operators report when using Hostaway alone: manually scheduling and coordinating cleaners, no visibility into whether properties are actually guest-ready, maintenance requests getting lost, and team communications scattered across text threads. Keepers automates all of this so you can focus on growing your portfolio, not managing chaos.
How does AI photo verification work for my Madison properties?
After each turnover clean, your cleaner submits photos through the Keepers mobile app. Keepers' AI reviews every photo against your property-specific checklist — flagging missed items, dirty surfaces, or staging issues. You receive an alert if anything needs attention before your Madison guest checks in, preventing the 1-star reviews that come from a non-guest-ready property.
How quickly can I set up Keepers for my Madison Hostaway portfolio?
Most Madison operators are fully onboarded within one week. Keepers' team assists with property setup, cleaner onboarding, and Hostaway integration so your first automated turnover runs smoothly. Most operators see measurable time savings within the first two weeks of going live.
Can Keepers help me scale my Madison STR portfolio on Hostaway?
Yes. Keepers is built to scale with your Madison portfolio. Whether you manage 5 or 500 properties, the platform automates the coordination work that grows linearly with unit count — cleaning scheduling, quality verification, maintenance routing, and team communications — so you can expand your Hostaway portfolio without adding operations overhead.
What does Keepers cost for Madison operators using Hostaway?
Keepers offers flexible pricing based on your portfolio size and the features you need. For Madison operators currently using Hostaway, we offer a streamlined onboarding path that has you running automated turnovers quickly. Book a free demo at usekeepers.com/demo to get a custom quote for your Madison operation.

Related Topics

Hostaway Keepers Madison, WISTR software Madison, WIKeepers Madison, WI

Keepers — The #1 STR Operations Platform

Automate turnovers, manage maintenance, coordinate your team, and scale your short-term rental portfolio — all in one place.

Book a Free Demo → Explore Features