Earn more from stays already booked.
Paid early check-ins, late checkouts, and other approved extras can add income without another booking. We offer them to guests and coordinate the details with your local team.
GUEST UPSELLS · HANDLED FOR YOU
VACATION RENTAL MANAGEMENT. BUILT BY OPERATORS. VETERAN-OWNED
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
A SMALL MONTHLY FEE. A BIGGER PURPOSE.The goal? A team that
The goal? A team that
more than earns its fee.
We look for ways your rental can earn more while taking the daily work off your plate. The upside is yours. Our management fee stays at $397 per property, per month.
Give your listing more reasons to win.
Your FREE onboarding review looks at titles, photos, amenities, and booking friction—with recommendations designed to improve visibility and turn more interest into bookings.
LISTING OPTIMIZATION REVIEW · FREEGet out of the day-to-day.
Guest messages, cleaner schedules, maintenance follow-ups, reviews, and AirCover claim support move to our team. Your rental gets a system. You get room for your life.
DAILY OPERATIONS · OFF YOUR PLATEPUT THE FEE IN PERSPECTIVEIt doesn’t take a second property
It doesn’t take a second property
to create another income opportunity.
For illustration: eight approved extras contributing $50 each after platform and fulfillment costs would cover the $397 management fee.
ILLUSTRATIVE MONTHLY EXAMPLE
8×$50=$400
Extras × contribution per extra = contribution before management
Enough to cover the $397 feeThe example is not a forecast. Upsell demand, availability, costs, and results vary. Listing changes and spending are agreed with you; extra earnings aren’t guaranteed.
Find the opportunities in my listingTHE WORK. THE OWNERS. THE OUTCOMES.Better systems.
Better systems.
Bigger possibilities.
Jennifer started without operating systems. Her revenue doubled through her work with Matthew. Here’s what changed for her and other owners.
Jennifer D.
Client outcome2×revenue
From no systems to twice the revenue.
- The work
- Jennifer started without operating systems. Matthew helped improve the property and business through consulting and operations automation.
- The reported outcome
- Her revenue doubled, and daily operations were automated. More income potential—and less work landing on the owner.
No systems → automated operations
Richard R.
Client outcome+50%revenue
More revenue. More properties.
- The work
- Business consulting and operations automation to improve how the rental business runs.
- The reported outcome
- Revenue increased by 50%. Richard has added 3 properties since they began working together.
3 properties added
Preston M.
Client outcome5+properties added
Room for the next chapter.
- The work
- Property design, consulting, and automated operations with Matthew and his team.
- The reported outcome
- Preston increased revenue and has added 5+ properties since they began working together.
Design + operations + growth
Selected outcomes from Matthew’s prior consulting and operations work, as reported by Matthew. These individual experiences include work beyond the $397 operations plan. Results vary; revenue growth is not the same as profit growth.
Let’s talk about my rentalTHE PORTFOLIO BEHIND KEYSIDETop 1%. Top 5%.
Top 1%. Top 5%.
Built on great hosting.
Standout rentals from Matthew’s hosting and co-hosting portfolio. Real Airbnb recognition. Real guest feedback. The experience we bring to your property.
Meet your host on Airbnb
AIRBNBTop 1%of eligible listings
NASHVILLE, TN
Cowgirl Heaven
A colorful Broadway getaway · hosted with Genevie
AIRBNBTop 5%of eligible listings
SAVANNAH, GA
The Savannah suite
2 bedrooms · shared pool & gym access
AIRBNBTop 5%of eligible listings
MANCHESTER, TN
The Manchester getaway
3-bedroom townhome · arcade games & family stays
5.0 for communication. Across all three.Because a beautiful property needs a team that takes care of the guest experience.
CHECKED OCT 9, 2026SELECTED PRAISE FROM REAL GUESTSResponsive hosting.
Responsive hosting.
In our guests’ own words.
Quick replies. Helpful answers. A host who goes the extra mile. These are the details guests call out in their own reviews.
10 / 10 · VRBOOUTSTANDING COMMUNICATION
“Communication with the host was outstanding”
10 / 10 · VRBOABOVE & BEYOND
“Matthew went above and beyond to ensure we had a great stay. … Communication was great. Responded quickly to messages sent.”
10 / 10 · VRBOQUICK REPLIES. FRIENDLY SUPPORT.
“The host was very quick to respond when we had questions and was very friendly. I would definitely go back.”
10 / 10 · VRBORESPONSIVE HOSTING
“Matthew was a wonderful and responsive host. … We definitely plan on coming back!”
Airbnb designations are based on ratings, reviews, and reliability among eligible listings. Ratings and designations checked October 9, 2026 and may change. These selected guest-review excerpts describe portfolio stays, not the $397 management service. The Manchester photo is lightly edited and virtually styled; Nashville and Savannah use their listing photos. Individual results vary.
CONSIDERING EVOLVE OR VACASA?Meet the team that lets
Meet the team that lets
you keep more.
Already have a rental and local people you trust? Get the operations team behind it for one predictable fee.
THE 20% FEE COMPARISONSame $60,000
Same $60,000
in annual bookings.
An illustrative management-fee comparison for one property.
AT A 20% MANAGEMENT FEE$12,000management fees / year
WITH KEYSIDE · $397 / MONTH$4,764management fees / year
MORE MONEY YOU KEEP+$7,236/ yearCalculate with your revenue
20% is an example rate, not Evolve’s or Vacasa’s quoted rate. Savings compare management fees only, assume equal booking revenue, and exclude other expenses. Service scopes differ.
WHY KEYSIDE FITS ESTABLISHED RENTAL OWNERSLess on your plate.
Less on your plate.
More on your terms.
01
Your revenue grows. Our fee stays flat.
$397 per property per month. No percentage of your booking revenue. More bookings never trigger a higher Keyside management fee.
02
Your business stays yours.
Keep your listings, reviews, payouts, and major decisions. We take over the daily guest and vendor conversations.
03
An operator’s team. In your corner.
Matthew built a portfolio of 30+ properties. His team brings those operating systems to your rental, with his personal listing and upsell review included FREE at onboarding.
04
Try the team for 30 days.
Cancel at the end of your first 30 days and we’ll refund your full first $397 management fee. A clear way to see if Keyside works for you.
How the service models compare
Choose the team and scope that fit your property.
Keyside
$397/ property / month- 24/7 guest support & review responses
- Cleaner, maintenance & inspection coordination
- AirCover claim support & approved upsells
- FREE personal onboarding review
- First-fee 30-day money-back guarantee
Works with your local providers. Ongoing pricing is outside this plan.
Evolve
10–15% of booking revenueTRADEOFFS TO CONSIDER
- Your fee grows with bookings.A percentage of revenue means a bigger management fee as bookings grow.
- An extra onboarding charge.Published new-owner setup: $250, plus $25 per additional property.
View published service scope
Listing marketing, dynamic pricing, guest communication, and remote 24/7 support. Owners select a local Guest Contact for on-site help. Six-month satisfaction guarantee, subject to its terms.
Core: 10%. Plus: 15%. Pro pricing is custom.
Vacasa
Custom quoteTRADEOFFS TO CONSIDER
- You need a quote to know the fee.Pricing is tailored to your property and market. There’s no published universal flat rate.
- May overlap with help you already have.If you already have local care and pricing support, compare what you need with a full-service package.
View published service scope
Listing marketing, dynamic pricing, 24/7 guest support, a dedicated local property manager, professional home care, and on-the-ground support.
Compare your actual quote and scope with Keyside’s $397 operations plan.
The Keyside fit: You have an active rental and local providers, and want a team to own the everyday coordination. Cleaning, repairs, inspections, platform charges, and other property expenses are separate. Evolve and Vacasa include ongoing pricing; Keyside’s $397 plan does not. A percentage fee can cost less at lower revenue.
Published sources & comparison details · checked October 9, 2026
Based on each provider’s published services. Confirm current quotes and terms. Different service models can produce different costs and revenue; savings are not guaranteed. Keyside is independent of Evolve and Vacasa.
PUT THE $397 FEE IN PERSPECTIVEMore money you keep.
More money you keep.
More time you reclaim.
Paying a manager? Compare the fees. Managing it yourself? See what handing off the daily work could be worth to you.
START WITH YOUR SITUATION
ALREADY PAYING A PERCENTAGE FEE?Calculate what
Calculate what
you could keep.
$0$50,000
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+$1,203extra / month
$14,436more 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$397/mo
Let’s talk about my rentalCURRENTLY DOING IT ALL YOURSELF?What is your
What is your
time back worth?
Think about guest messages, cleaner check-ins, vendor calls, and chasing the next update. Use your own estimates.
hours / week
0 hours40 hours
/ hour
These are your estimates, not a promise of hours saved or extra income. We confirm which tasks you can hand off before you start. Months are averaged using 52 weeks ÷ 12.
YOUR ESTIMATED VALUE OF TIME BACK$1,083of your time / month
21.7 hoursyou estimate you could hand off per month
Use that time for your family, your work, or simply being off duty. This is the value you place on your time, not cash savings or rental profit.
Your Keyside management fee$397/mo
About 1.8 hours a week.At $50 per hour, that much time back equals the $397 monthly fee in personal time value.
Compare the full service, too. Keyside’s $397 plan covers daily operations. Ongoing pricing and revenue management are outside this plan. See exactly what’s included.
THE WORK THAT NEVER STOPS. NOW IT HAS A TEAM.Hands-off daily hosting.
Hands-off daily hosting.
That’s what the team is for.
No more being the go-between for every guest, cleaner, and repair. We handle the everyday conversations and follow-through. You keep control of spending limits and major decisions.
01 / INCLUDED
24/7
Guest management & review responsesYour guests get a team. You get your nights back.
Booking questions, check-ins, 2 a.m. issues, and checkout details. We handle guest conversations and thoughtful review responses.
Messages · Check-ins · Review responses
02 / INCLUDED
Turnovers.
Cleaner coordinationA cleaner handoff. Every time the calendar changes.
Schedules, access, guest changes, and cleaning follow-up. We keep your cleaner in the loop so you can get out of the group chat.
Scheduling · Property notes · Follow-up
03 / INCLUDED
Inspections.
Inspection coordinationKnow what needs attention. Have a team on it.
We arrange monthly or agreed inspections, collect local updates, and coordinate the next steps when something needs attention.
Local checks · Photos & notes · Next steps
04 / INCLUDED
Repairs.
Maintenance coordinationStop being the middleman for every maintenance call.
We talk to guests and vendors, arrange access, and follow up. Spending and escalation follow the limits you approve.
Vendor contact · Access · Status updates
05 / INCLUDED
AirCover.
AirCover claim supportThe claim needs follow-through. We handle it.
We organize photos and records, support eligible claim submissions, and follow up with Airbnb. Airbnb decides eligibility and payment.
Evidence · Submission · Follow-up
06 / INCLUDED
Upsells.
Approved guest upsell coordinationGive the guests you already have more ways to spend.
Early arrivals, late checkouts, and approved paid extras. We handle the conversation and check availability with your local team.
Approved extras · Guest offers · Coordination
We coordinate the work. Your local team carries it out. Cleaning, inspections, repairs, and other property costs are separate from the management fee.
SEE THE HANDOFF IN ACTIONThe message comes in.
Example workflowsThe message comes in.
Your team takes it from here.
- 01Guest support
We take the conversation.
Check the arrival details and walk the guest through the property’s access instructions.
- 02Local coordination
We work the backup plan.
If needed, contact the agreed local person and coordinate access using your escalation plan.
- 03Follow-through
We check the outcome.
Confirm the next step with the guest and keep track of any follow-up needed.
Where you come in: You’re involved if the agreed escalation plan calls for an owner decision or a serious issue needs your attention.
Examples show how coordination works, not a response-time promise. Local attendance depends on provider availability; emergencies may require local emergency services.
HAND OFF THE WORK. KEEP THE CONTROL.Still your property.
Still your property.
Now with a team behind it.
You shouldn’t have to choose between doing everything yourself and losing visibility into your own business.
Your listings. Your reviews.
Keep the rental business you’ve built. We agree on co-host or team access and permissions before the handoff.
Your payouts. Your upside.
We review payout settings together. Our management fee is $397 per property, not a percentage that rises with your revenue.
Your local team, coordinated.
Keep working with your cleaner and maintenance contacts. We handle the schedules, questions, and follow-up.
Your rules. Your approvals.
Set spending limits and escalation instructions with us. Major decisions stay with you; the everyday back-and-forth comes to us.
THE PEOPLE BEHIND THE PROCESSMatthew’s operating team.
Matthew’s operating team.
Working with your local people.
- MatthewPersonal onboarding review & consultation
- Keyside operationsGuest conversations & daily coordination
- Your local providersCleaning, inspections & physical repairs
WHY OWNERS CHOOSE KEYSIDEExperienced operators.
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.
$397 per property per month, with no percentage of booking revenue. Try the service for 30 days, backed by our first-month refund guarantee.
THE HOST BEHIND THE SERVICE
Matthew Tregoning
Founder, Keyside
See the hosting experience behind our management service on my Airbnb profile.
View my Airbnb host profileOpens 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.
YOUR ONBOARDING REVIEW · FREEFind the opportunities
Personally reviewed
by Matthew Tregoning
Find the opportunities
in your rental.
01A stronger first impression
02Clear reasons to book
03Paid extras guests may value
04Your priorities, walked through
Personally reviewedby Matthew Tregoning
FREE when you onboard
FREEPERSONAL LISTING REVIEW
+ UPSELL CONSULTATION
INCLUDED WHEN YOU ONBOARD+ UPSELL CONSULTATION
Let’s find what could
earn you more.
Matthew personally reviews your listing for missed earning opportunities: a stronger first impression, clearer reasons to book, and paid extras that fit your guests.
A better first impression can help a guest choose your place. A useful paid extra can add value to a stay already on the calendar. We help you identify those opportunities in one FREE onboarding review and consultation.
Give guests more reasons to book.
We review titles, photo order, descriptions, and amenities across your platforms, with visibility and booking conversion in mind. You get specific improvements and clear priorities for your property.
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.
Have a team handle the follow-through.
We flag gaps in your setup, including your pricing approach, and agree on listing improvements. Our ongoing team offers approved extras and coordinates with your cleaner, so each request doesn’t come back to you.
FREE when you onboard.No extra consultation fee.Let’s talk about my rental
MATTHEW TREGONINGFounder. Operator. Air Force veteran.
A REAL OPERATOR IN YOUR CORNER.FROM ONE RENTAL OPERATOR TO ANOTHERFrom 30+ properties
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 $397 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 rentalYOUR TIME BACK. MORE WAYS TO EARN. ONE FLAT FEE.Your hosting team.
Your hosting team.
$397 a month.
A team to run daily hosting and pursue extra income through approved upsells. Your personal listing optimization review is FREE, and your first fee is backed by our 30-day guarantee.
YOUR OPERATIONS TEAM
$397/ month
Per property. One flat management fee.
- 24/7 guest management & review responses
- 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.
Ongoing pricing and revenue management are outside this plan. Third-party services and property expenses are separate.
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 $397 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.
THE FIRST STEP IS SIMPLEA clear handoff.
01 02 03
A clear handoff.
A stronger start.
Tell us what’s on your plate.
Send your property details. We’ll discuss your setup and confirm whether the $397 operations plan covers what you need. No payment to inquire.
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.
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 $397 management fee.
BEFORE YOU HAND OVER THE INBOXFair questions.
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 questionSTART WITH YOUR PROPERTY. NO PAYMENT REQUIRED.Let your rental do more.
Let your rental do more.
Let yourself do less.
Show us your rental. We’ll talk through where it could earn more, what we can take off your plate, and how the $397 plan fits your business. No payment to start the conversation.
Matthew TregoningFounder, Keyside
$397 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 $397 management fee back.
KeySideLLC@gmail.com