As the calendar flips to 2026, there’s never been a better time to pause, reset, and set your short-term rental (STR) up for its strongest year yet. Whether you own a single coastal condo or a portfolio of homes across Northeast Florida, January is your annual opportunity to get organized, streamline operations, update your property, and reposition your listing for higher occupancy and higher nightly rates all year long.
At Joseph Ellen Properties, we treat the start of every year like a strategic relaunch. A “clean slate” mindset opens the door to more revenue, better guest experiences, stronger reviews, and smoother operations—for you and your property manager. And while the market changes, guest preferences evolve, and new platforms emerge, one thing remains true: the STRs that intentionally reset each year consistently outperform those that don’t.
This guide walks you through every essential step to prepare your vacation rental for a successful 2026—from pricing strategy to design refreshes, taxes to tech, operations to guest experience. Use it as your annual roadmap to elevate your rental, remove friction, and maximize returns.
- Start With a Deep Operational Audit
Before you upgrade, repaint, restyle, or reprice anything, start with a steady baseline: What is actually happening inside your property?
January is the perfect time for a full operations and system review, including:
✔ Inventory Audit
Go room-by-room and confirm:
- Kitchen items are complete and up to standard
- Linens and towels match required counts and quality
- Consumable kits are fully stocked
- Outdoor items (grill tools, cushions, umbrellas) are present and functioning
- Electronics, chargers, games, and remotes haven’t walked away
Small missing items create big guest frustrations—replacing these early prevents complaints before they start.
✔ Maintenance Walkthrough
Your annual reset must include:
- HVAC filter changes
- Dryer vent cleaning
- Appliance tests
- Hot tub/pool equipment inspections
- Lightbulb and battery checks
- Touch-up paint on high-traffic walls
- Door code system tests
- Plumbing flush and leak checks
Preventive maintenance saves owners thousands each year. One missed leak can silently cost you more than a year of proactive service visits.
✔ Safety + Compliance
Verify that:
- Fire extinguishers are present and up to date
- Smoke detectors and CO2 detectors are tested
- Stairs, railings, and decks are secure
- Locks and smart deadbolts function reliably
- Required State of Florida and county-level STR paperwork is renewed or current
A safe home is a profitable home—and non-negotiable for liability.
- Review Your Rental Performance From 2025
To plan for a stronger year, you need to understand how last year performed.
Most STR owners never fully analyze their data. But at Joseph Ellen Properties, we encourage owners to treat their rental like a business—because that’s exactly what it is.
Here are the key questions to evaluate:
✨ Occupancy
- Were you consistently booked?
- Which months dipped below expectations?
- How did your occupancy compare to your market average?
✨ Pricing
- Did your nightly rates align with demand?
- Were you priced too low during high-season?
- Were you overpriced during slower months?
Underpricing hurts revenue… but overpricing damages occupancy.
✨ Revenue
- What were your monthly gross earnings?
- How did this compare to projected numbers?
- What drove strong or weak months?
✨ Review Score Trends
- Which compliments appeared most often?
- Which complaints repeated themselves? (These are your 2026 priorities.)
✨ Platforms
Where did your bookings come from?
- Airbnb
- Vrbo
- Direct Booking
- Return Guests
- Referral guests
- Travel nurses/corporate
For 2026, shifting more revenue toward direct bookings is already a major industry trend—and one that benefits owners significantly.
Once you understand the story your 2025 numbers are telling, you can build a roadmap for a better 2026.
- Refresh Your Property for the New Year
The beginning of the year is the ideal moment to improve the look, feel, and functionality of your short-term rental—especially because guests expect fresh, clean, updated spaces after the holiday rush.
Aesthetic Refresh Ideas (That Make a Big Impact)
✔ New Bedding + Pillows
Nothing transforms a space faster—or earns better reviews—than fresh, crisp bedding.
✔ Repaint High-Traffic Areas
Hallways and entryways usually need it first.
✔ Swap Dated Decor
Photos, pillows, throws, small accessories—keep your look modern and inviting.
✔ Upgrade Lighting
Warm lighting increases perceived value instantly. Swap bright blue or cold bulbs with soft white LEDs.
✔ Add Weather-Resistant Outdoor Touches
- New cushions
- Patio string lights
- Small herb planter
- Fire pit refresh
Outdoor spaces photograph exceptionally well.
✔ Consider a Small-Scale Design Upgrade
If you want a bigger jump in revenue, January is the best time to complete:
- Accent walls
- Kitchen hardware updates
- New living room furniture
- Artwork upgrades
- Smart storage solutions
Design enhancements often deliver some of the highest ROI of any STR improvement.
Check out Joseph Ellen Designs for inspo or redesign help!
- Update Your Listing for 2026 (Photos, Description, Amenities)
Your listing should evolve every year. January is your chance to revamp it for stronger performance.
✔ Update Photography
If you made any upgrades, get new photos immediately. Fresh images help you:
- Rank higher
- Increase clicks
- Improve conversion
- Refresh your brand presence
✔ Rewrite Your Description
This is a great time to:
- Highlight new amenities
- Add 2026 seasonal features
- Improve SEO wording
- Showcase proximity to the year’s biggest events
Listings that are rewritten annually outperform static, stale descriptions.
✔ Update Amenity List
Guests expect:
- Coffee station essentials
- Streaming platform access
- Fast Wi-Fi
- Outdoor relaxation areas
- Well-stocked kitchens
- Family-friendly items
- Desks or workspaces
Today’s traveler is more demanding than ever—make sure you’re delivering what they’re searching for.
- Reevaluate Your Pricing Strategy for 2026
If you’re not adjusting pricing during the reset, you’re leaving money on the table.
Your New-Year Pricing Checklist
- Review 2025 pacing, ADR, and occupancy
- Adjust high-season rates upward based on demand
- Re-map shoulder seasons
- Add event-based pricing (Nights of Lights, TPC, spring break, holiday weekends, festivals)
- Ensure cleaning fees are competitive
- Evaluate discounts, minimum stays, and turnaround rules
The key to a profitable STR is strategic pricing—not static pricing.
✨ Tip:
Your 2025 data is the most accurate predictor of your 2026 potential. Let it guide your decisions.
- Refresh Your Guest Experience
January is an excellent time to updat your guest communications and add small touches that enhance reviews.
✔ Upgrade Your Welcome Book
Include:
- Updated check-in instructions
- New local restaurant + activity recommendations
- 2026 event calendars
- House rules written in friendly, guest-focused language
- Wi-Fi information and QR codes
- Local emergency numbers
✔ Improve Pre-Arrival Messaging
Guest satisfaction often hinges on communication. Update:
- Check-in messages
- Early check-in/late check-out policies
- Parking directions
- Pet policies
- Technology instructions
✔ Add Bonus Touches
Consider:
- Digital guidebooks
- Refillable consumables kits
- Locally roasted coffee
- Small welcome snacks
- A branded photo moment for UGC
Guests remember how your property made them feel.
- Streamline Your Operations + Tech Stack
Your 2026 reset should include a review of all systems that keep your STR running behind the scenes.
Evaluate Your Tech Tools
Are you using:
- A smart lock system?
- Automated messaging?
- A comprehensive PMS?
- Channel management?
- A dynamic pricing tool?
- Noise monitoring?
- Wi-Fi mesh systems?
- Owner dashboards?
If any of these were inconsistent or outdated in 2025, January is the perfect time to fix or replace them.
Reassess Your Vendors
Your cleaners, handymen, pool techs, and inspectors play a huge role in guest satisfaction. Confirm:
- They are reliable
- They have clear 2026 expectations
- They are priced competitively
- They have capacity during high-season
Vendor consistency equals guest consistency.
- Review Your Tax + Compliance Requirements
January is tax prep month for STR owners, and it’s important to begin early.
✔ Gather 2025 income statements
You’ll need:
- 1099s
- Home expenses you can write off
- Depreciation schedules
- Mortgage interest statements
- Utilities
- Insurance documents
✔ Review Lodging Tax Requirements
Ensure:
- Monthly REMITTANCES are submitted
- County and state filings are up to date
✔ Plan for 2026 Tax Strategy
Talk with a STR-knowledgeable CPA about:
- Bonus depreciation
- Cost segregation studies
- Material participation
- Passive vs active status
- Capital improvements timeline
The strongest STR owners treat taxes as a strategy—not just a requirement.
- Evaluate Your STR Insurance Policy
Insurance evolves every year—so should your coverage.
Key Areas to Review
- Appropriate dwelling coverage
- Contents coverage
- Liability limits
- Loss-of-income protection
- Storm deductibles
- Flood insurance requirements
Property policies are not “set it and forget it.” Reassess annually to stay protected.
- Revisit Your STR Goals for 2026
Your property is part of your financial strategy—so your goals matter.
Before the year accelerates, pause and answer:
Why am I hosting this home?
- Cash flow?
- Long-term appreciation?
- Hybrid personal/vacation use?
- Preparing for future sale?
- Seasonally renting only?
What are my 2026 targets?
- Revenue increase percentage
- Occupancy targets
- Upgrade budget
- Project list
- Adding or removing platforms
- Adding properties to your portfolio
When you know your goals, every decision becomes simpler.
- Build Your 2026 Project Roadmap
Once all audits, evaluations, and plans are complete, create a 12-month timeline that breaks your year into manageable sprints.
Quarter 1: Foundation & Refresh
- Design upgrades
- Listing overhaul
- Photography
- Operational fixes
- New tech install
- Tax prep
Quarter 2: Guest Experience Enhancements
- Outdoor living upgrades
- Guidebook refresh
- Amenity upgrades
- Summer pricing adjustments
Quarter 3: Growth Strategy
- Direct booking focus
- SEO improvements
- Social media + UGC plan
- Partnering with local businesses
Quarter 4: Holiday + Event Prep
- Nights of Lights setups
- TPC readiness
- Winter maintenance
- High-season pricing
A simple plan leads to outstanding results. If JEP is managing you home, the marketing, growth strategies and holiday prep are all covered!
Conclusion: Start 2026 With Confidence and Clarity
Your annual STR reset is more than a checklist—it’s a strategic opportunity to create a year of strong financial performance, better guest experiences, and smoother operations. The work you put in now sets the tone for the next twelve months.
And you don’t have to do it alone.
At Joseph Ellen Properties, our team manages this reset for you—ensuring your property is positioned to win in 2026 from day one. From design enhancements and operational audits to pricing strategy, direct booking optimization, and guest experience systems, we handle the details so you can enjoy the results.
Here’s to a profitable, streamlined, and standout 2026.
Your property deserves it. And so do you.