B4K Vacation Home Rentals

10/19/2026

📣 [JOB OPENING IN ANNAPOLIS] We are seeking a reliable, detail-oriented team member to support our short-term rental operations in Annapolis, Md. This role combines quality assurance, laundry services, and light property support to ensure each home is guest-ready and maintained to high standards.

🔑 Key Responsibilities:
Conduct thorough walkthroughs of homes after guest check-outs to perform quality assurance checks
Identify and report any cleanliness, maintenance, or inventory issues using the company app
Pick up, wash, dry, fold, and return laundry to designated properties
Assist with basic troubleshooting of minor issues within the home and communicate findings
Occasionally pick up and restock supplies from storage or local stores as needed

✅ Qualifications:
Strong attention to detail and ability to spot inconsistencies
Reliable transportation and valid driver’s license
Ability to manage time efficiently and work independently
Comfortable using mobile apps for reporting and communication

😄 What We Offer:
Flexible scheduling
Independent work environment
Opportunity for growth within the company
Competitive pay based on experience

➡️ Application Details:
This position is located in Annapolis, Md.

Job seekers should submit a resume, cover letter, and references to: [email protected].

Apply now!

10/15/2026

Following the October 12, 2026 Annapolis City Council Regular Meeting, I wanted to share the City’s short-term rental update, along with my observations.
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My takeaway: we are still hearing many of the same concerns, with few concrete answers about implementation. The City’s Planning and Zoning staff acknowledged that they do not currently have enough staffing, time, or technology to administer and enforce the program at the level being discussed. No new STR rules were adopted during this briefing.
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Meeting background
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The official agenda item was “Short-Term Rental Moratorium Update” (ID-164-26), an interim briefing required under Ordinance O-40-25. Planning and Zoning Director Chris Jakubiak and Senior Comprehensive Planner Alexis Robinson presented the findings and answered Council questions. This was a City staff briefing, not a task force meeting.
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The meeting was held in the Mayor John T. Chambers, Jr. City Council Chambers. Confirmed Council participants included Mayor Jared Littmann, Aldermen Harry Huntley, Brooks Schandelmeier, Frank Thorp, Rob Savidge and Keanuú Smith-Brown, and Alderwomen Karma O’Neill and Janice Allsup-Johnson. Published minutes are still pending, so this is not a complete attendance roll.
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The STR presentation begins around 2:33 in the meeting recording. The portion reviewed consisted of staff presentations and Council questions, with no public remarks during that segment. A separate general public-comment period occurred earlier.
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Enforcement and staffing
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Staff reported approximately 303 licensed STR units and 65 identified unlicensed rentals as of September 30, with at least 30 active enforcement cases. They acknowledged that the actual number of unlicensed rentals is likely higher.
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Mayor Littmann questioned why all identified unlicensed properties were not already subject to enforcement. Staff attributed the gap to limited capacity and the time required to process cases.
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Alderwoman O’Neill asked how the City could respond to situations such as Friday-afternoon arrivals at an unlicensed rental. Staff said they do not yet have a practical solution for real-time enforcement, although coordination between police, 311, and City systems is being explored.
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Alderman Thorp requested a concrete estimate of what it would cost to operate and enforce the program at the level residents expect.
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For homeowners, this leaves an important question unanswered: what will a workable program actually require, and what will it cost?
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Fines and compliance
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The recently increased maximum fine of $5,000 was discussed as a deterrent. Mayor Littmann suggested sending notices about the increased penalty to identified operators without active enforcement cases.
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Alderman Schandelmeier asked whether the higher fine would improve compliance and why some operators remain unlicensed. Director Jakubiak said the fine should be a meaningful deterrent and that the City hopes not to collect it.
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The lottery and technology gaps
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In response to Alderman Huntley’s questions, staff explained that the existing lottery is scheduled to begin November 1, 2027. Applicable license periods will shorten during the phase-in because they cannot extend beyond that date.
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Staff also acknowledged that the systems needed to administer the block-face limits and lottery still require development. The cost and practical mechanics of running the lottery remain unresolved.
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Host Compliance and the reliability of the data
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The City said it continues to use Host Compliance data to identify unlicensed rentals. Alderman Huntley asked whether the figures were comparable to earlier reports, and staff confirmed that the same platform was being used.
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Separately, I have concerns about that system. My understanding has been that Host Compliance is Canadian-based and has become difficult to reach, but I have not independently confirmed its current corporate location or support arrangements. I also question whether the City still uses it for tax reporting.
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If the City is relying on this platform to support regulatory decisions, I would like clear answers about how current and accurate the data is, how errors are corrected, and what support is available. These are my questions—not findings presented by the City.
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Potential changes—not adopted rules
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Staff outlined possible changes, including clearer distinctions between owner-occupied homes and commercially operated investment properties, limits on annual rental days, zoning restrictions, higher operating standards, a citywide license cap, and increased fees.
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Director Jakubiak emphasized a potential approach that would distinguish occasional rentals of someone’s own home from properties operated primarily as commercial investments.
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These remain preliminary ideas. Staff said further research and community engagement would take place before proposed legislative changes are drafted.
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A stronger homeowner voice through ASTRA
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Local property managers are coming together through ASTRA (Annapolis Short-Term Rental Association), led by Sean and Jen from iTrip, to share information and bring homeowner and property-manager perspectives into the discussion.
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I encourage you to join, stay informed, and participate as the City develops its next recommendations.
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Join ASTRA on Facebook:
Link Below

These discussions concern properties within Annapolis city limits. Existing requirements remain in place. I’ll continue sharing updates as we receive concrete proposals and opportunities to provide input.
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Official meeting record:
Link Below
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Carolyn

10/13/2026

🍂 [ATTN: AIRBNB OWNERS IN ANNAPOLIS] Fall in Annapolis is not "business as usual" for Airbnb owners in Annapolis.

Think about what's going on:
🛥️ The Annapolis Powerboat Show
⛵️ The Annapolis Sailboat Show
🏈 USNA football weekends
🎭 The Maryland Renaissance Festival
🦃 Thanksgiving Break

More and more tourists, to Annapolis than in any other season! This means more turnovers, more guest, communication, more maintenance, and more moving parts!

➡️ And every guest still expects a seamless hospitality experience.

Trying to manage it all yourself means you are not just managing a property. You are managing a constant operation.

But B4K brings an entire team of experts to the job. Imagine:
Every guest inquiry → answered.
Every price → strategically adjusted.
Every cleaning → coordinated on time.
Every maintenance request → completed.
Every detail → prioritized.

Best of all -- you don't lift a finger!

Make the most of your Airbnb in Annapolis this fall! Book a call with B4K today to discuss our amazing property management services! Unlock the difference:
https://blueprints4keys.com/get-started/

10/11/2026

🍂 Fall is one of the most exciting times to visit Annapolis! From boat shows and Navy football to pumpkins, spooky tours, Renaissance festivities, and the kickoff of the holiday season, there is plenty to experience!

Discover what is happening this fall and start planning your getaway. Read the blog and plan your stay!

Fall is the busiest time of year in Annapolis! There are many exciting events happening in Annapolis in the Fall, you can see why tourists flock here!

10/09/2026

ANNAPOLIS SAILBOAT SHOW: Book your Airbnb with easy access to City Dock now!

This waterfront space is a short drive to City Dock and offers:
⛵️private pier and boat slip
⛵️gorgeous sunsets
⛵️3 comfortable bedrooms
⛵️spacious deck

This Airbnb is available now but it won’t last long!

A waterfront home on Cadle Creek with its own pier and boat slip, a wide west-facing deck, and sunsets over the Rhode River. Three bedrooms plus den a...

10/07/2026

⚓️ [COMMISSIONING WEEK 2027] Commissioning Week is one of the most meaningful times of the year in Annapolis! Will you be in town to celebrate your Midshipman?

Finding the right Airbnb in Annapolis will make Commissioning Week all the more memorable! B4K has an extensive selection of Annapolis vacation rentals, including:

⚓️ Spacious homes for families and groups
⚓️ Charming historic townhomes
⚓️ Comfortable bungalows
⚓️ Convenient locations near USNA

Booking early gives your family more choices and more time to plan the celebration.

Commissioning Week 2027 will be here before you know it - book your Airbnb in Annapolis now! https://blueprints4keys.com/listings/

10/05/2026

⚓️ 🏈 [USNA HOMECOMING GAME] Book your Airbnb for USNA's Homecoming Game!

On Saturday, October 24, Navy takes on North Texas at Navy-Marine Corps Memorial Stadium! Will you be there?

Make the most of your time in Annapolis, and book a convenient, comfortable stay at one of our nearby Airbnbs! Our vast inventory of Airbnbs in Annapolis include:
✅ Waterfront retreats
✅ Spacious family-friendly homes
✅ Cozy downtown apartments
✅ Charming historical townhomes

PLUS our Annapolis-located team is ready to assist you! As Annapolis experts, the team at B4K responds quickly and provides helpful guidance to make your stay in Annapolis stress-free!

Don't wait - book now!
https://blueprints4keys.com/listings/

10/01/2026

🛥️ [AIRBNBs AVAILABLE] The Annapolis Powerboat Show is fast approaching, and we have limited Airbnbs available!

☀️ Clean & comfortable
☀️ Conveniently located
☀️ Locally managed

Book your Airbnb in Annapolis now to enjoy one of Naptown’s most iconic events!



https://blueprints4keys.com/listings/



Our inventory of vacation rentals near Annapolis is always growing! Access our full list here, and book your next getaway!