If you bought an Orlando vacation rental during the post-pandemic boom, you’re likely sitting on a mountain of equity. But as the market shifts, many hosts are asking the same question: Should I sell my Orlando vacation rental now or hold onto it?
Yes, 2025 is an excellent time to sell your Orlando vacation rental.
While Orlando’s tourism engine continues to roar, the ground is shifting for property owners. Rising management costs, new regulations, and increasing inventory are creating a complex landscape. For profit-focused investors, 2025 presents a strategic window to cash out at the market’s peak.
Here are the key data points and market trends to help you decide if now is the best time to sell your short-term rental investment.
Market Timing Has Never Been Better
Orlando’s real estate market in 2025 occupies a sweet spot that benefits sellers. While inventory has increased compared to the frenzied seller’s market of 2021-2022, demand remains robust from both investors and traditional homebuyers.
The number of homes for sale in Orlando has jumped significantly. According to local real estate expert Barrett Spray, active listings climbed from 9,300 in April 2024 to 13,300 in April 2025. This means more competition for sellers.
The median home price sits around $389,900, representing remarkable appreciation from just five years ago. More importantly, properties are still selling at or near these elevated prices, allowing owners to lock in substantial gains.
Current market indicators favor sellers:
- Properties typically sell within 70 days
- Motivated buyers remain active in the market
- Financing remains available despite higher interest rates
- Resort communities continue commanding premium prices
Unlike 2021’s bidding wars, today’s market allows for more strategic pricing while still achieving strong sale prices. You won’t face the pressure of having to accept the first offer, but you also won’t wait months for serious interest.
Vacation Rental Performance Has Plateaued
The explosive growth in short-term rental income, which is characterized by 2021-2023, has leveled off significantly. Rent growth across Orlando has flattened to just 1-2% annually. A stark contrast to the double-digit increases many owners enjoyed during the pandemic boom.
Key rental market shifts:
- Average Orlando rents have stagnated at around $1,900 monthly
- Vacancy rates have climbed to approximately 9%
- New construction has flooded the market with additional rental inventory
- Competition for guests has intensified dramatically
While Orlando remains a strong tourism destination with over 75 million annual visitors, the rental income that once seemed guaranteed now requires more effort, better marketing, and competitive pricing to achieve.
Many owners are discovering that their “passive income” has become far more hands-on.
Rising Operational Costs Are Squeezing Profits
Florida’s insurance crisis has hit vacation rental owners particularly hard. Property insurance premiums have skyrocketed, sometimes doubling or tripling annual costs. Combined with rising property taxes, maintenance expenses, and management fees, the profit margins on many vacation rentals have shrunk considerably.
Consider these mounting costs:
- Insurance premiums up 50-100% in many areas
- Property management fees typically run 8-10% of rental income
- Maintenance reserves of 5-10% needed for HVAC, appliances, and repairs
- Marketing and booking platform fees continue to rise
For owners who purchased at today’s elevated prices, the math often no longer works. Properties that generated strong cash flow when purchased for $300K may barely break even at current market values of $450K+.
Tax Advantages May Be Disappearing
The current capital gains environment offers several benefits that may not persist indefinitely. If you lived in your vacation rental as a primary residence for two of the last five years, you could exclude up to $250,000 (or $500,000 for couples) in capital gains from federal taxes.
Additionally, with talks of potential changes to tax policies, locking in gains under current rates might prove advantageous. The 15% long-term capital gains rate many investors enjoy could face adjustments in future legislation.
For properties acquired years ago at significantly lower prices, selling now allows you to capture appreciation while tax advantages remain favorable.
Reinvestment Opportunities Are Emerging
Smart investors aren’t just selling. They’re repositioning. The capital freed up from selling an Orlando vacation rental can be deployed into:
Higher-yielding opportunities:
- Multi-family properties in emerging markets
- Commercial real estate with stronger cap rates
- Diversified investment portfolios
- Other real estate markets with better fundamentals
Using a 1031 exchange, you can defer capital gains taxes while moving into properties with superior cash flow potential. Many former vacation rental owners are finding better returns in traditional rental properties or commercial assets.
Making the Strategic Decision
Consider selling your Orlando vacation rental now if:
- You’ve achieved your target return on investment
- You want to diversify into other markets or asset classes
- Managing the property no longer fits your lifestyle
- You need liquidity for other opportunities
- Your property requires significant capital improvements
The current market provides excellent conditions for motivated sellers while maintaining enough buyer demand to ensure competitive offers.
Get Ahead of the Competition
While Orlando is still one of the best places for a vacation rental, the secret is out. New construction in resort communities is adding thousands of new units to the short-term rental market. Selling your property now means getting ahead of this wave of new inventory, which will only increase competition for bookings and potentially drive down nightly rates.
Working With Orlando’s STR Sales Expert
Successfully selling a vacation rental requires understanding both traditional real estate sales and short-term rental valuations. Mike Chen brings unique expertise as both a practicing Airbnb host and an experienced realtor in Orlando.
Mike’s dual perspective includes:
- Over 2,600 guest reviews as an active Superhost
- Deep knowledge of STR-friendly communities and their performance
- Understanding of vacation rental income potential and limitations
- Expertise in marketing to both investors and traditional buyers
Whether you’re looking to time the market perfectly or need to sell due to changing circumstances, Mike can position your property to attract serious buyers while maximizing your return on investment.
Ready to explore your selling options?
The vacation rental landscape has undergone a fundamental shift. What worked in 2022 may not work in 2025, but selling at the right time, with the right strategy, still offers significant opportunities.
Schedule your free consultation with Mike Chen to discuss your property’s current value, market timing, and optimal exit strategy.
Call (321) 430-8681 today—the best-selling opportunities won’t wait forever.
