Winter Haven, Florida Short-Term Rental Market
The Polk County STR market around Winter Haven posted $183 ADR, 44.9% occupancy and $2,381 monthly revenue in September 2026.
Quick Answer: Winter Haven, Florida is an active short-term rental market. average occupancy in the Lakeland/Winter Haven market area is 45%. average monthly revenue in the Lakeland/Winter Haven market area is $2,381. average daily rate in the Lakeland/Winter Haven market area is $183. the top operator in the Lakeland/Winter Haven market area is Evolve with 179 listings. market score is 87/100 (grade A).
Market data reflects the Lakeland/Winter Haven regional market, which includes Winter Haven. Regulations, taxes, and permit details below are specific to Winter Haven.
Market Score Breakdown
Five dimensions StaySTRA evaluates per market.
Market Overview
This profile covers Winter Haven and the surrounding Polk County, Florida STR market. Short-term rental performance is tracked at a shared level for Winter Haven, Haines City, Polk City and Lakeland, so every performance number below describes the Polk County STR market rather than Winter Haven alone. Bedroom, channel and listing-type counts, along with top operator names, are tracked at a shared regional level rather than uniquely for Winter Haven, so this profile omits them.
In September 2026, the Polk County STR market averaged an average daily rate of $183 and an occupancy rate of 44.9%, producing average monthly revenue of $2,381 per listing. Compared with September 2025, occupancy rose 0.9%, ADR rose 5.6% and revenue rose 2.6%. September is the seasonal low point for the region, so these readings sit below the annual picture. Year to date in 2026 (nine months), occupancy has averaged 58.4% with an ADR of $216 and monthly revenue of $3,483. For full-year 2025 the figures were 58.2% occupancy, a $205 ADR and $3,234 in monthly revenue.
Winter Haven sits in Polk County between Tampa and Orlando. The city is home to LEGOLAND Florida Resort and Peppa Pig Theme Park, and LEGOLAND alone draws more than 1.5 million visitors a year. Polk County recorded 5.55 million visitors from April 2024 to March 2025, up 5% year over year. The Winter Haven Chain of Lakes, with 50 lakes inside city limits, supports boating, fishing and water sports, and the area also draws retirees and snowbirds in winter and sports tourism groups. Winter Haven has a population of about 55,200 and benefits from spillover from Walt Disney World traffic roughly 30 miles away. The mix of theme park demand, lake recreation and a growing metro area gives the market several separate sources of bookings.
Seasonal Patterns
| Month | Occupancy |
|---|---|
| Jan | 50% |
| Feb | 69% |
| Mar | 71% |
| Apr | 56% |
| May | 52% |
| Jun | 63% |
| Jul | 66% |
| Aug | 56% |
| Sep | 43% |
| Oct | 55% |
| Nov | 53% |
| Dec | 54% |
Month-by-month nightly rates and revenue figures for Winter Haven are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Top Short-Term Rental Operators in Lakeland/Winter Haven market area
Ranked by total active listings. Useful for understanding the competitive landscape. Operator data is published for the Lakeland/Winter Haven market as a whole, which includes Winter Haven, so these counts are not Winter Haven-only figures.
| # | Operator | Listings | Reviews | Rating |
|---|---|---|---|---|
| 1 | Evolve | 179 | 4,635 | ★ 4.57 |
| 2 | RedAwning | 164 | 793 | ★ 4.24 |
| 3 | Vacasa | 126 | 2,251 | ★ 4.42 |
| 4 | Top Villas | 111 | 493 | ★ 4.47 |
| 5 | Master Vacation Homes | 99 | 3,309 | ★ 4.73 |
What Kind of STR Should I Buy in Winter Haven?
Revenue and nightly-rate breakdowns by bedroom count, property tier, and dwelling type for Winter Haven 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 | 40.2% |
| vrbo | 10.5% |
| both | 49.3% |
Home Value Trends (Winter Haven)
Typical home values, median sale prices, and the 10-year price trend for Winter Haven are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Insights
Booking-window and length-of-stay analysis for Winter Haven — how far ahead guests book and how to price around it — is available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Short-Term Rental Regulations
Short-term rentals are permitted in Winter Haven. The city does not have a dedicated STR licensing ordinance, and Florida Statute 509.032(7) preempts the city from banning vacation rentals or restricting how often or how long they can be rented. Winter Haven is not grandfathered under the pre-2011 carveout, so these protections apply. Enforcement severity is rated low.
Operators need two licenses. The first is a Florida DBPR Vacation Rental License, which costs about $250 initially and around $150 at biennial renewal. The second is a City of Winter Haven Business Tax Receipt issued by the Building Division, which renews annually and is due October 1. No city-specific STR permit exists. Operators must also register with the Florida Department of Revenue for sales tax.
The combined transient rental tax is roughly 12%. That is made up of the 5% Polk County Tourist Development Tax, 6% Florida state sales tax and the 1% Polk County discretionary sales surtax. Airbnb and Vrbo collect and remit these taxes on the host’s behalf in most cases.
There is no cap on nights per year, and neither owner occupancy nor primary residence is required. Properties must comply with general zoning, building, property maintenance, smoke detector and carbon monoxide detector rules administered by the Winter Haven Planning Division. New accessory dwelling units are barred from short-term rental use for 10 years after construction. The DBPR conducts random audits with penalties up to $1,000 per day for noncompliance. Governor DeSantis vetoed SB 280 in June 2024, which would have added a statewide registry, and Winter Haven has not adopted a new local STR ordinance since.
Market Comparison
The Polk County STR market in September 2026 ran at 44.9% occupancy and a $183 ADR. September is the weakest month in the region, so a fairer comparison uses the annual picture. Year-to-date 2026 occupancy is 58.4% with a $216 ADR. Full-year 2025 showed 58.2% occupancy and a $205 ADR.
The region reached $248 in June and $246 in July, but it gives that back in the fall and spring shoulder periods. In September 2026, professionally managed listings reached a $244 ADR and luxury listings reached $376.
Growth is a point in the market’s favor. September 2026 ADR was up 5.6% year over year, which is stronger than occupancy growth of 0.9%. Information on top operators is tracked at a shared regional level rather than uniquely for Winter Haven, so this profile omits it. Investors comparing Polk County with other Florida markets should weigh the lower entry cost, with a typical home value of $275,573, against the lower fall occupancy.
Frequently Asked Questions About Winter Haven, Florida
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