Winter Park, Florida Short-Term Rental Market
Quick Answer: Winter Park, Florida is an active short-term rental market. average occupancy is 62%. average monthly revenue is $4,482. average daily rate is $267. the top operator is Master Vacation Homes with 1,891 listings. market score is 96/100 (grade A).
Market data reflects the Orlando regional market, which includes Winter Park. Regulations, taxes, and permit details below are specific to Winter Park.
Market Score Breakdown
Five dimensions Apivex evaluates per market.
Seasonal Patterns
| Month | Occupancy | ADR | Revenue |
|---|---|---|---|
| Jan | 54% | $210 | $3,075 |
| Feb | 70% | $219 | $3,687 |
| Mar | 71% | $244 | $4,493 |
| Apr | 60% | $232 | $3,550 |
| May | 55% | $209 | $3,033 |
| Jun | 65% | $244 | $3,955 |
| Jul | 66% | $238 | $4,128 |
| Aug | 56% | $216 | $3,321 |
| Sep | 46% | $190 | $2,402 |
| Oct | 56% | $198 | $2,846 |
| Nov | 55% | $214 | $2,960 |
| Dec | 56% | $230 | $3,273 |
Top Short-Term Rental Operators in Winter Park
Ranked by total active listings. Useful for understanding the competitive landscape.
| # | Operator | Listings | Reviews | Rating |
|---|---|---|---|---|
| 1 | Master Vacation Homes | 1,891 | 73,946 | ★ 4.75 |
| 2 | Top Villas | 1,319 | 6,477 | ★ 3.85 |
| 3 | Ohana Vacation | 808 | 3,603 | ★ 4.21 |
| 4 | Vacasa | 762 | 13,386 | ★ 4.38 |
| 5 | RedAwning | 657 | 4,363 | ★ 4.12 |
What Kind of STR Should I Buy in Winter Park?
Revenue and pricing by property type, tier, and bedroom count.
Revenue by Bedroom Count
| 1 bed | 10,090 |
| 2 bed | 7,112 |
| 3 bed | 12,048 |
| 4 bed | 11,748 |
| 5 bed | 21,520 |
ADR by Property Tier
| Entire Home | $276 |
| Luxury | $494 |
| Professionally Managed | $311 |
Revenue by Dwelling Type
| Apartment | $3,332 |
| Entire Place | $4,636 |
| House | $5,175 |
Booking Channel Mix
Distribution of bookings across major STR platforms.
| Channel | Share |
|---|---|
| airbnb | 36% |
| vrbo | 12.7% |
| both | 51.2% |
Investment Analysis
Revenue Trend (5 yr)
ADR & Occupancy Trends (5 yr)
Run a Free Address Analysis
Skip the market averages. Get revenue projections, comp analysis, and ROI for your specific property address. Free, instant, no signup required.
Analyze My Property →Home Value Trends (Winter Park)
Analyze Winter Park Rentals
Use our free calculator to estimate Airbnb revenue for any property in Winter Park.
Free Winter Park STR Calculator →
