30-day money-back guarantee

Cancel at the end of your first 30 days and get your $500 management fee back.

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A blue-accented guest bedroom at a 1st Class Rentals property
VACATION RENTAL MANAGEMENT. BUILT BY OPERATORS. VETERAN-OWNED

More from your rental.
More time for you.

Hand off the guest messages, cleaners, and maintenance follow-ups. We also help you find ways to earn more through a stronger listing and paid guest extras.

$500 / monthPer property. One flat management fee.FREE listing & upsell review when you onboard

Start with a conversation. No payment to inquire.

MORE EARNING OPPORTUNITIES. INCLUDED FROM THE START.A personal listing review + an upsell consultation. FREE.
$5M+

booking revenue generated

2,000+

five-star guest reviews

5 years

as an Airbnb Superhost

30+

hosts helped reach Superhost

MATTHEW’S CLIENT WORK

More revenue.
Room to grow.

Revenue growth, expanding portfolios, and operations that run more smoothly. Selected results from Matthew’s consulting, design, and operations work.

David T.

Consulting & operations automation

6 properties.
His life back.

Matthew helped David automate operations across his 6-property business. With the daily workload handled, David got his time back and a rental business that no longer took over his life.

Daily operations automated. More time to live.

Vincent R.

Consulting & operations automation

2 properties.
More freedom.

Matthew helped Vincent automate operations across his 2-property business. Getting the day-to-day off his plate meant more time for his own life, with systems in place to support ongoing rental cash flow.

Operations handled. His time back.

Selected outcomes from Matthew’s prior consulting and operations work, as reported by Matthew. These summaries describe individual client experiences; results vary. Revenue growth is not the same as profit growth.

Let’s talk about my rental
WHY OWNERS CHOOSE KEYSIDE

Experienced operators.
Working on your side.

Hands-on hosting experience, a personal review from Matthew, and a flat fee that lets you keep the upside as your booking revenue grows.

The same team. The same systems.

Matthew grew his own portfolio to over 30 properties. Keyside brings the operations team and systems behind that business to your rental.

Time back. Income opportunities.

24/7 guest support and vendor coordination, plus a personal listing and upsell review to identify ways your rental could earn more.

A flat fee. A real guarantee.

$500 per property per month, with no percentage of booking revenue. Try the service for 30 days, backed by our first-month refund guarantee.

95.2%

of our Airbnb ratings were five stars.

Across our portfolio over the prior year, as reported in September 2026.

THE HOST BEHIND THE SERVICE
Matthew Tregoning

Matthew Tregoning

Founder, Keyside

See the hosting experience behind our management service on my Airbnb profile.

View my Airbnb host profile

Opens on Airbnb in a new tab.

Portfolio figures are reported by 1st Class Rentals as of September 2026. The 95.2% figure covers Airbnb ratings over the prior year. These are guest ratings from our rental portfolio, not owner testimonials for this management plan. Past results do not guarantee future performance.

A thoughtfully furnished living room in our Jacksonville portfolio
YOUR ONBOARDING REVIEW · FREE

Find the opportunities
in your rental.

01A stronger first impression
02Clear reasons to book
03Paid extras guests may value
04Your priorities, walked through
FREE when you onboard
FREE LISTING & UPSELL REVIEW

Let’s find what could
earn you more.

Matthew personally reviews your listing and talks through ways to improve bookings and add income from the guests you already attract.

One review and consultation when you onboard. Included FREE with management.

01

Give guests more reasons to book.

We review your title, photos, description, and amenities to identify strengths you could highlight and unclear details that may make guests hesitate.

02

Find paid extras that fit your property.

We discuss early check-in, late checkout, and other useful extras your guests may pay for. You approve the options; availability and your local team’s capacity come first.

03

Have a team handle the follow-through.

You get prioritized listing recommendations. Our ongoing service handles approved upsell conversations and coordination with your cleaner, so each request doesn’t land back on you.

FREE when you onboard.No extra consultation fee.Let’s talk about my rental
GET MORE OUT OF OWNING A RENTAL.

Your rental has potential.
Your time has value.

You want a property that earns well and leaves room for your life.

A guest needs help at 2 a.m. Your cleaner needs an answer. It leaves little time to revisit your listing or explore paid extras your guests might value.

Keyside takes on the daily coordination and helps you spot opportunities to improve what your rental brings in.

A STRONG FIT FOR OWNERS WITH
  • An active short-term rental
  • A local team to coordinate
  • A goal to earn more while doing less
THE WORK THAT NEVER STOPS. NOW IT HAS A TEAM.

You hand off the inbox.
We own the follow-through.

One point of contact for guests, cleaners, and maintenance. Clear expectations. Fewer things coming back to you.

01
24/7 guest management

Guests taken care of. Around the clock.

Booking questions, check-in instructions, late-night issues, and checkout details. We handle the conversation and the follow-through, so being a host doesn’t mean always being available.

02
Cleaner coordination

Turnovers without the group-text chaos.

We coordinate schedules, share property notes, communicate guest changes, and follow up on cleaning issues. Your cleaner has a point of contact. It doesn’t have to be you.

03
Inspection coordination

Eyes on the property. A plan for the details.

We arrange monthly or agreed inspections with local help, gather updates, and coordinate the work that needs attention. Small issues get a next step.

04
Maintenance coordination

One less repair to chase down.

We speak with guests and vendors, arrange access, and track the follow-up. You approve decisions within the spending and escalation process we agree on together.

05
AirCover claim support

Support when a stay doesn’t go to plan.

Photos, documentation, eligible claim submissions, and follow-up with Airbnb. We manage the process; Airbnb determines whether a claim qualifies and what it pays.

06
Guest upsell coordination

Give each stay more ways to earn.

A guest may happily pay for an earlier arrival or a later checkout. We coordinate your approved paid extras when the schedule allows, handle the conversation, and check availability with your cleaner.

We coordinate the work. Your local team carries it out. Cleaning, inspections, repairs, and other property costs are separate from the management fee.

Matthew Tregoning, founder of Keyside
MATTHEW TREGONINGFounder. Operator. Air Force veteran.
A REAL OPERATOR IN YOUR CORNER.
FROM ONE RENTAL OPERATOR TO ANOTHER

From 30+ properties
to your operations team.

I’m Matthew—an Air Force veteran, dad, and rental operator. I grew my portfolio to over 30 properties. That meant a lot of guest messages, turnovers, and maintenance to keep on top of. I made it work by building a strong team and a system for the day-to-day.

Along the way, I realized this is what I’m really good at: managing operations and making rental businesses run better. I built Keyside to bring that same team and those same systems to other operators.

Now you can put us to work for $500 per property a month, without handing over a percentage of your bookings. I personally review your listing and upsell opportunities when you join, and my team handles the daily coordination.

Matthew TregoningFOUNDER, KEYSIDE
Let’s talk about my rental
YOUR TIME BACK. MORE WAYS TO EARN. ONE FLAT FEE.

Your hosting team.
$500 a month.

Daily operations handled, a FREE listing and upsell review when you join, and a clear 30-day money-back guarantee.

YOUR OPERATIONS TEAM
$500/ month

Per property. One flat management fee.

  • 24/7 guest management
  • Cleaner & turnover coordination
  • Monthly or agreed inspection coordination
  • Maintenance coordination
  • AirCover claim support
  • Approved guest upsell coordination
FREE listing & upsell reviewPersonal recommendations to help your rental earn more. One time at onboarding.
Let’s talk about my rental

Third-party services and property expenses are separate.

THE KEYSIDE GUARANTEE

30-day
money-back guarantee.

Try Keyside for 30 days. If you decide to cancel at the end of that period, we’ll refund your full $500 management fee.

What’s covered
Your first month’s management fee.
How to claim
Email us at the end of your first 30 days to cancel and request your refund.

Cleaning, repairs, inspections, platform charges, and other property expenses are separate and aren’t included in the refund.

ALREADY PAYING A PERCENTAGE FEE?

See how much more
you could keep.

$0$25,000

These are management-fee savings. Extra income from listing improvements or upsells is not included. Other property expenses are separate; compare service scope and how each provider defines revenue.

MORE MONEY YOU KEEP+$1,100extra / month
$13,200more money you keep per year

Money that stays with you instead of going toward management fees. Annual savings assume the same monthly revenue and fee rate for 12 months.

Management fee at 20%$1,600/mo
Your Keyside management fee$500/mo
Let’s talk about my rental
THE FIRST STEP IS SIMPLE

A clear handoff.
A stronger start.

01

Tell us what’s on your plate.

Send your property details. We’ll discuss your setup and confirm whether the $500 operations plan covers what you need. No payment to inquire.

02

We get the details right.

We agree on co-host access, vendors, spending approvals, and a service start date. You keep the big decisions. Matthew leads your FREE listing and upsell review to identify earning opportunities.

03

Put us to work.

We take over the agreed daily operations. Try us for 30 days. Cancel at the end of that period and we’ll refund your first $500 management fee.

BEFORE YOU HAND OVER THE INBOX

Fair questions.
Straight answers.

You should know exactly what you’re handing off, what stays with you, and what the fee covers.

Ask Matthew a question

START WITH YOUR PROPERTY. NO PAYMENT REQUIRED.

Get more from
owning your rental.

Tell me what you want to improve: your income, your workload, or both. We’ll discuss your property and confirm the scope and handoff before you commit.

Matthew Tregoning
Matthew TregoningFounder, Keyside
$500 per property / month FREE listing & upsell review at onboarding 30-day money-back guaranteeCancel at the end of your first 30 days and get your first $500 management fee back.
info@1st-class-rentals.com
START WITH A CONVERSATION

Tell us about your rental.

Send the basics. We’ll follow up by email to talk about your goals, explain what we can take over, and plan the next step.

We use these details to respond to your inquiry. Privacy

30-day money-back guarantee
$500/moPer property
Let’s talk about my rental