Orlando remains one of the most active short-term rental markets in the U.S., with tens of millions of visitors each year driven by theme parks, conventions, and international travel. Yet for property owners, the real challenge in 2025 isn’t demand. It’s choosing the right short-term rental management company.
Most owners aren’t asking, “Who has the lowest fee?”
They’re asking something more practical:
Why does my Orlando Airbnb underperform while similar homes earn more, and who can actually fix that?
This guide compares the top short-term rental management companies in Orlando, FunStay Florida, Vacasa, Evolve, Grand Welcome, and local boutique managers across pricing, services, owner experience, and performance approach.
The goal isn’t to rank “best vs worst,” but to help owners understand which management model fits their property, involvement level, and risk tolerance.
The Orlando Short-Term Rental Landscape in 2025 (Context Matters)
Orlando’s average Airbnb occupancy sits around 65%, with average daily rates typically ranging from $140–$160. Top-performing homes exceed those numbers substantially, but not because of luck or location alone.
In 2025, performance is driven by:
- Dynamic pricing tied to school calendars, conventions, and flight demand
- Airbnb SEO listing optimization and conversion quality
- Review momentum and response times
- Local regulatory compliance
- Operational execution (cleaning, maintenance, turnovers)
The right management company influences all these. The wrong one quietly limits them.
Neutral Comparison Table
| FunStay Florida | Vacasa (Casago) | Evolve | Grand Welcome | Local Managers | |
| Management Fee | ~15–20% | ~25–35% | 10%–15% | ~18–22% | 10–20% |
| Setup / Onboarding Fees | Varies | Varies | None | ~$500 | $250–$500 |
| Pricing Control | Local, daily | Centralized | Automated | Local + algorithm | Varies |
| Listing Optimization | Ongoing | Initial + periodic | Initial focus | Ongoing | Varies |
| Cleaning & Maintenance | Fully managed | Fully managed | Owner-managed | Fully managed | Fully managed |
| Guest Communication | Local team | Centralized | Centralized | Local team | Local |
| Owner Visibility | Real-time portal | Owner dashboard | Owner dashboard | Owner portal | Varies |
| Contract Flexibility | 30-day exit | Longer terms | Flexible | Moderate | Varies |
| Best Fit For | Hands-off, performance-driven | Scale & brand reach | DIY owners | Full-service w/ structure | Owners wanting personalization |
This table is the decision engine. The sections below explain why these differences matter.
FunStay Florida (Local, Performance-Driven Management)
FunStay Florida is a boutique, locally operated short-term rental management company focused exclusively on the Orlando area. Their model emphasizes hands-on oversight, dynamic pricing, and continuous listing optimization.
Unlike national property managers, FunStay’s pricing and operational decisions are made locally, with daily adjustments tied to Orlando-specific demand drivers such as school calendars, convention schedules, and seasonal travel patterns.
Owners who switch to FunStay often cite clearer visibility into performance, faster issue resolution, and stronger review momentum. The model favors ongoing optimization, not a “set it and forget it” approach.
Best suited for owners who want:
- Active pricing control
- Transparent performance tracking
- Local accountability
- Full-service management without long lock-ins
Vacasa (Now Under Casago)
Vacasa is one of the largest vacation rental management companies in North America and now operates under the Casago umbrella. Its biggest strength is scale, national brand recognition, broad marketing reach, and standardized systems.
However, that scale comes with tradeoffs. Pricing decisions are largely centralized, and service consistency can vary by region. Management fees are among the highest in the market, and many services are bundled into add-on packages.
Vacasa works best for owners who prioritize:
- Brand recognition
- Hands-off management
- Nationwide infrastructure
It is less ideal for owners seeking fine-tuned local pricing or frequent listing optimization.
Evolve (Marketing-First, Hybrid Model)
Evolve operates as a marketing and booking platform, not a traditional full-service manager. Their lower fee structure appeals to cost-conscious owners, but cleaning, maintenance, and local compliance remain the owner’s responsibility.
This model can work well for Orlando owners who:
- Live locally or have trusted vendors
- Want professional listing creation and distribution
- Are comfortable managing operations themselves
Performance depends heavily on owner involvement. Homes without strong local execution often struggle with review consistency and operational friction.
Grand Welcome (Structured Full-Service)
Grand Welcome positions itself between boutique and national operators. They offer full-service management with local teams, supported by standardized systems and revenue management tools.
Their approach is more structured than small local firms but more localized than national brands. Setup fees are common, and pricing is generally mid-range for full-service management.
This option suits owners who want:
- A defined management structure
- Local guest support
- A balance between automation and oversight
Local Orlando Property Managers (Boutique Firms)
Orlando has many independent property managers offering personalized service and flexible contracts. Quality varies widely.
Strong local managers can outperform larger brands when they combine:
- True local pricing expertise
- Hands-on owner communication
- Consistent operations
However, smaller teams may face capacity constraints during peak seasons, and marketing reach is often limited compared to national platforms.
Why These Differences Affect Performance
Two similar homes in the same Orlando neighborhood can produce dramatically different results because:
- Pricing frequency matters — static pricing loses revenue weekly
- Airbnb SEO listing optimization affects visibility and conversion
- Response times and review velocity directly influence ranking
- Local regulation mistakes create risk and downtime
Management companies don’t just “manage”. They define the systems that control these outcomes.
Choosing Based on Ownership Style (Not Hype)
- If you want maximum involvement and lower fees, Evolve may fit
- If you want scale and brand recognition, Vacasa is an option
- If you want a structured full-service with local teams, Grand Welcome fits
- If you want local, performance-driven Airbnb property management in Orlando, FunStay tends to align best
There is no universal “best,” only the best fit.
Decision Checklist (Read This Before Choosing)
Before choosing Airbnb property management in Orlando, ask:
- Who controls pricing daily, and how often is it adjusted?
- How frequently is my listing optimized for Airbnb SEO and conversion?
- How do I see performance in real time (not just monthly summaries)?
- Who handles local compliance, inspections, and tax filings?
- What happens if it’s not working? How easy is it to exit?
Owners who clearly answer these questions usually make confident decisions and avoid costly mistakes.
In Orlando’s competitive 2025 short-term rental market, success isn’t about demand. It’s about execution, transparency, and local expertise. Comparing management companies by model, not marketing promises, is the fastest way to protect both revenue and peace of mind.
