Annapolis, Maryland · Vacation rental management

The local team with the big-company playbook.

Local people on the ground, a full technology stack behind them, and books that are always clean. You own it; we run it.

Localteam on the ground
in Annapolis
Trustaccounting on every
owner account
Taxes& licensing
filed for you

Commissioning Week, included.  Every home we manage is automatically enrolled in our Commissioning Week program. We build your CW listing free, and House Kee homes are featured on the CW page. Manage on your own? You can still list your home on our Commissioning Week page.

Commissioning Week program →
Why Annapolis earns

A calendar full of reasons to visit

Annapolis demand follows the Naval Academy and the water. We price every one of these weekends on purpose, not by accident.

Late May

Commissioning Week

Graduation week. Families book a year ahead, and it brings the year's highest rates.

Summer

Induction Day & Plebe Parents Weekend

New midshipmen arrive, then families come back to visit.

Sept – Nov

Navy football Saturdays

Home games fill downtown and Eastport with alumni and fans.

October

U.S. Sailboat & Powerboat Shows

Two of the country's biggest in-water boat shows, on back-to-back weekends.

Spring – Fall

Sailing season

Wednesday-night races, regattas and harbor weekends keep the calendar busy.

Guests plan their trip on our Annapolis destination guide, which has local tours and things to do.

The technology behind your rental

Enterprise-grade tools

Distribution

Your home is listed and tuned on the largest booking platform.

Distribution

Reaches families and larger groups, who book longer stays.

Distribution

Reaches international and business travelers.

Operations hub

One calendar, guest messaging and digital guidebooks across every channel. No double bookings.

Revenue management

Revenue experts optimize your rates, fees and listing so your home earns more.

Dynamic pricing

Rates adjust every day for demand, events and seasonality.

Smart access & safety

SuiteKeeper sets a unique lock code for every guest. SuitePortal gives guests check-in details. SuiteVerify checks guest ID.

Trust accounting

Bookkeeping and clear monthly owner statements.

Tax & licensing

Lodging taxes reported and paid. Licenses tracked and renewed.

Reputation

Every review from every platform in one place, so we see and respond to all of them.

Direct booking

Our own booking site. Repeat guests book direct and skip platform fees.

Self-managing hosts usually piece these tools together one at a time, if they use them at all. Every home The House Kee manages gets the full stack from day one.
Your money, handled properly

Trust accounting, real statements, taxes paid

Most managers keep this in a spreadsheet. Ours runs like a professional firm.

  • Trust accounting. Guest funds sit in a dedicated trust account, so your owner account is always funded and fully reconciled.
  • Professional bookkeeping. Every booking, fee and expense is recorded and categorized.
  • Monthly owner statements from VRPlatform. They're easy to read and ready for your accountant.
  • Lodging taxes reported and paid by LodgeCompliance: Maryland sales tax, plus Annapolis or Anne Arundel County hotel tax.
  • Licensing and inspections handled by LodgeCompliance. That covers the City of Annapolis short-term rental license and County registration for homes outside city limits.
Protection

Properly insured, so your investment is protected

Not every property manager carries insurance, and fewer carry the right coverage. We've made a serious investment in ours, because your home is on the line.

Our coverage · Strategic partner

General liability and E&O

The House Kee carries general liability and errors & omissions coverage through Wister Insurance, specialists in insuring short-term rental managers. The company caring for your home is covered too, not just the home itself.

Recommended for owners

Coverage built for rentals

Standard homeowner policies often aren't written for short-term rental use. For your own policy, we recommend Proper Insurance, which is designed specifically for vacation rentals.

Ask every manager you interview: do you carry general liability and E&O coverage? It's one of the clearest signs of a professional operation.
Property Care

Every home guest-ready. Every issue moving. Every owner informed.

Our Head of Property Care handles maintenance in every market, from the first report until the job is closed.

Informed

You hear from us

We keep you posted on anything that affects guests or needs a real repair, and you always know where each job stands.

Vetted

Local vendor bench

Trusted Annapolis handymen, HVAC techs, plumbers, electricians and locksmiths we know and rely on.

Watchful

Eyes on every turnover

Our cleaning team flags damage, wear and low supplies after stays, so small issues get handled before they grow.

Documented

Before & after photos

Every job is logged with notes, the vendor, the cost and photos.

Protected

Spending guardrails

Routine fixes are approved within your contract limit. Bigger decisions always come to you first.

Prioritized

Urgent issues first

Lockouts, leaks and heating or AC problems go to the front of the line.

thehousekee.com
The House Kee direct booking website
Direct booking

Your home on our own booking site

Every home we manage gets its own page on thehousekee.com, with live availability and secure checkout. It's a booking channel you don't share with millions of other listings.

  • Best rate, no booking-site markup. Guests skip platform service fees, which gives them a reason to book direct.
  • Past guests become repeat guests. Direct guests join our guest list, so we can invite them back for the next Navy weekend or Commissioning Week.
  • Featured on our Commissioning Week page. House Kee homes get top billing during the biggest week of the Annapolis year.
  • Destination guides and local experiences keep guests planning their trip on our site, not someone else's.
  • Less dependence on any one platform. If Airbnb or Vrbo changes the rules, your home still has its own channel.

Visit our booking site →Annapolis guide

OUR PORTFOLIO

Annapolis Rentals We Manage

Reviews

What guests say about our Annapolis homes

Recent stays at Annapolis homes we manage, from Airbnb, Vrbo and Booking.com.

★★★★★

“What a beautiful, immaculately clean home in a terrific location. The host was absolutely wonderful with thoroughly kind communications.”

Margaret · Airbnb · Aug 2026
★★★★★

“The hosts take the time to clean. They even vacuum the couch after each guest. Communication was clear and prompt throughout our visit.”

Laurick · Airbnb · Aug 2025
★★★★★

“Our group of 5 had a great stay for plebe parent weekend. Plenty of space, clean, great location. Communication with the host was easy.”

Karin · Airbnb · Aug 2026

“They are honest, trustworthy and they outperformed any expectations that we had about a property management company. They have the property owner’s best interest.”

Clara · Homeowner · Google review

FAQS

Annapolis, MD Vacation Rental Management FAQs

How much does a vacation rental manager cost in Annapolis, MD?

Our fee is a percentage of your net nightly rate — not your total booking revenue. That distinction matters more than it sounds like it would.

Some property managers quote a percentage but apply it to the full top-line booking total, which often includes the cleaning fee, the guest service fee, and sometimes taxes passed through the platform. Those pass-through amounts inflate the number their percentage is taken from, even though none of that money is actually rental income you’re keeping. The result is a management fee that’s quietly larger than it looks.

We only take our percentage from the nightly rate itself — the actual rental income. Cleaning fees, taxes, and platform charges pass through untouched. It’s a simpler, more transparent way to align our fee with what you’re really earning, and we’re happy to walk you through exact numbers once we’re discussing your specific property.

Every home we manage runs on the same professional systems, so you never have to buy, learn or maintain them yourself:

  • Distribution: your listing on Airbnb, Vrbo and Booking.com, managed from one calendar in Hostfully
  • Pricing: PriceLabs dynamic pricing plus revenue management from Pacer
  • Access and safety: SuiteOp smart locks with a unique code for every guest, digital check-in and guest ID verification
  • Accounting: VRPlatform trust accounting and monthly owner statements
  • Reputation: Revyoos, so every review on every platform gets seen and answered
  • Direct booking: your home’s page on thehousekee.com

Owners who self-manage usually pay for tools like these one by one. We’ll walk through pricing for your home on a discovery call.

In most cases, yes — the City of Annapolis requires short-term rental operators to hold the appropriate local license, and homes just outside the city limits fall under Anne Arundel County’s rules instead. State and local lodging taxes also apply, and the requirements can change year to year. We manage licensing, inspections, and tax remittance for the owners we work with, so staying compliant isn’t something you have to track yourself.

Guest payments are held in a dedicated trust account, kept separate from our operating funds and reconciled through VRPlatform. That means your owner funds are always accounted for and your account is always funded.

Each month you receive a professional owner statement showing every booking, fee and expense, along with your owner payout. Statements are clear enough to hand straight to your accountant.

Yes. It’s your home. Tell us the dates you want and we’ll block them on every booking channel.

Before you decide, we’ll show you what peak dates like Commissioning Week, Navy football Saturdays and the boat shows typically earn in Annapolis, so you can choose which weekends to keep for yourself and which to rent.

Usually, yes. Standard homeowner policies often aren’t written for short-term rental use, so we recommend a policy built for it. Our recommended carrier for owners is Proper Insurance, which specializes in vacation rentals.

Separately, The House Kee carries its own general liability and errors & omissions (E&O) coverage through our partner Wister Insurance, so the company managing your home is insured too.

A traditional (long-term) property manager places a tenant on a lease for months or years and handles relatively infrequent turnovers. An Airbnb / short-term rental manager runs your home like a small hospitality business: dynamic nightly pricing, listing optimization across booking platforms, frequent professional turnovers and cleaning, and 24/7 guest communication. The House Kee specializes in the short-term side, which is what drives higher nightly revenue in an event-driven market like Annapolis, where Commissioning Week, the fall boat shows, and sailing season all command premium rates.

We manage short-term rentals throughout Annapolis and the surrounding Chesapeake Bay area — from the Historic District and Eastport to Murray Hill, West Annapolis, Annapolis Neck, and the Severn River communities, plus nearby Arnold, Edgewater, and Cape St. Claire. If you’re not sure whether your property qualifies, reach out and we’ll let you know right away.

Switching is more straightforward than most owners expect. We coordinate the transition around your existing reservations — honoring confirmed bookings, transferring guest details and calendars, and syncing your listings so nothing is double-booked or dropped. Most Annapolis owners transition outside the peak weeks — away from Commissioning Week in May and the fall boat shows — for the smoothest handoff, but we can work with any timeline. We’ll map out the whole process for you during your free consultation.

See what your Annapolis home could earn

Get a free projection built on real Annapolis demand, including Commissioning Week and Navy weekends. No obligation.

Get my free earnings analysis
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