Winter Park, Florida Short-Term Rental Market
Quick Answer: Winter Park, Florida is an active short-term rental market. average occupancy in the Orlando market area is 62%. average monthly revenue in the Orlando market area is $4,482. average daily rate in the Orlando market area is $267. the top operator in the Orlando market area 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 StaySTRA evaluates per market.
Seasonal Patterns
| Month | Occupancy |
|---|---|
| Jan | 54% |
| Feb | 70% |
| Mar | 71% |
| Apr | 60% |
| May | 55% |
| Jun | 65% |
| Jul | 66% |
| Aug | 56% |
| Sep | 46% |
| Oct | 56% |
| Nov | 55% |
| Dec | 56% |
Month-by-month nightly rates and revenue figures for Winter Park are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Top Short-Term Rental Operators in Orlando market area
Ranked by total active listings. Useful for understanding the competitive landscape. Operator data is published for the Orlando market as a whole, which includes Winter Park, so these counts are not Winter Park-only figures.
| # | 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 nightly-rate breakdowns by bedroom count, property tier, and dwelling type for Winter Park are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Channel Mix
Distribution of bookings across major STR platforms.
| Channel | Share |
|---|---|
| airbnb | 36% |
| vrbo | 12.7% |
| both | 51.2% |
Home Value Trends (Winter Park)
Typical home values, median sale prices, and the 10-year price trend for Winter Park are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Analyze Winter Park Rentals
Use our free calculator to estimate Airbnb revenue for any property in Winter Park.
Free Winter Park STR Calculator →
