Winter Haven, Florida Short-Term Rental Market
Winter Haven, FL STRs averaged $223/night at 60.3% occupancy in April 2026, with revenue up 12.6% year-over-year.
Quick Answer: Winter Haven, Florida is an active short-term rental market. average occupancy is 60%. average monthly revenue is $3,567. average daily rate is $223. the top operator is Evolve with 179 listings. market score is 87/100 (grade A).
Market Score Breakdown
Five dimensions Apivex evaluates per market.
Market Overview
Winter Haven is a Polk County city positioned between Tampa and Orlando, 30 miles from Walt Disney World, and home to LEGOLAND Florida Resort and Peppa Pig Theme Park. Polk County logged 5.55 million visitors between April 2024 and March 2025, up 5% year over year, and sports tourism alone generates more than $200 million annually. As of April 2026, the market posted an average daily rate of $223 and occupancy of 60.3%, generating a RevPAR of $135.
The market holds approximately 8,438 active listings, with entire-place rentals at 7,371 (87.4%), private rooms at 1,060 (12.6%), and 7 shared rooms. The bedroom distribution is unusual: 5-bedroom-plus units are the largest segment at 3,135 listings, followed by 1-bedroom (1,620), 4-bedroom (1,585), 3-bedroom (1,290), and 2-bedroom (798). This high concentration of large properties reflects the vacation-villa character of the market, where groups visiting LEGOLAND and Disney World rent multi-bedroom homes. Channel distribution shows 4,158 listings on both Airbnb and Vrbo, 3,392 exclusively on Airbnb, and 888 exclusively on Vrbo.
Year-over-year in April 2026: revenue grew 12.6%, with occupancy up 0.8% and ADR up 0.7%. The revenue growth score of 92.2 and investability score of 89.3 out of 100 are among the strongest readings in this batch. The total market score of 87.2 ranks second in this batch.
Seasonal Patterns
| Month | Occupancy | ADR | Revenue |
|---|---|---|---|
| Jan | 50% | $208 | $2,772 |
| Feb | 69% | $213 | $3,388 |
| Mar | 71% | $234 | $4,024 |
| Apr | 56% | $219 | $2,976 |
| May | 53% | $210 | $2,758 |
| Jun | 63% | $248 | $3,780 |
| Jul | 66% | $246 | $4,074 |
| Aug | 57% | $221 | $3,265 |
| Sep | 42% | $190 | $2,205 |
| Oct | 55% | $203 | $2,708 |
| Nov | 53% | $210 | $2,661 |
| Dec | 54% | $233 | $3,103 |
Top Short-Term Rental Operators in Winter Haven
Ranked by total active listings. Useful for understanding the competitive landscape.
| # | 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 pricing by property type, tier, and bedroom count.
Revenue by Bedroom Count
| 1 bed | 1,620 |
| 2 bed | 798 |
| 3 bed | 1,290 |
| 4 bed | 1,585 |
| 5 bed | 3,135 |
ADR by Property Tier
| Entire Home | $237 |
| Luxury | $416 |
| Professionally Managed | $287 |
Revenue by Dwelling Type
| Apartment | $3,234 |
| Entire Place | $3,795 |
| House | $3,670 |
Booking Channel Mix
Distribution of bookings across major STR platforms.
| Channel | Share |
|---|---|
| airbnb | 40.2% |
| vrbo | 10.5% |
| both | 49.3% |
Investment Analysis
Winter Haven offers the lowest entry cost of any market in this batch with among the highest gross yields. The typical home value is $276,487 and the median sale price is $253,333 as of April 2026. For-sale inventory is substantial at 777 active listings, and the sale-to-list ratio of 0.873 indicates buyers have negotiating room. At the average monthly revenue of $3,567, annualized gross revenue projects to approximately $42,804, implying a gross yield of roughly 15.5% against the typical home value.
This yield figure is exceptional relative to most STR markets and reflects both the market’s strong demand fundamentals and its relatively low home prices compared to coastal or mountain resort areas. Tier differentiation is meaningful: luxury-tier properties average $416/night versus the all-listings ADR of $223, 87% higher. Professionally managed listings average $287/night, a 28% premium over market.
Entire-place rentals outperform at $3,795/month versus $3,670 for houses and $3,234 for apartments. The 5-bedroom-plus segment (3,135 listings, 37.2% of total) anchors the market’s group-vacation-villa economy. Revenue growth of 12.6% year-over-year and an investability score of 89.3 make this one of the most compelling markets in this batch on a risk-adjusted basis, with low regulatory friction, Florida state preemption protecting operators, and a large, diverse demand base.
Revenue Trend (5 yr)
ADR & Occupancy Trends (5 yr)
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Booking Insights
Winter Haven guests book an average of 55.3 days in advance, the longest in this batch, reflecting the advance-planning behavior of group travel to theme parks and sports tournaments. LEGOLAND and Disney World visitors typically book accommodations 60 to 90 days ahead, particularly for spring break and summer weeks where demand is highest. Operators who update pricing and availability at least 90 days before peak season capture the highest-intent bookings.
Average length of stay is 4.95 nights, nearly 5 nights, among the longest in this batch. This extended stay reflects the multi-day theme park vacation pattern: guests arrive Sunday or Monday and depart after a week of park visits. Five-night stays align with theme park visit schedules and reduce turnover frequency to approximately 6 bookings per occupied month. A 4 to 5 night minimum aligns with demonstrated guest behavior and reduces per-booking cleaning costs.
Short-Term Rental Regulations
Winter Haven operates under one of Florida’s more permissive STR frameworks. The city does not have a dedicated STR licensing ordinance and is covered by Florida Statute 509.032(7), which preempts cities from banning vacation rentals or restricting their frequency or duration.
Operators must hold two items: a Florida Department of Business and Professional Regulation (DBPR) Vacation Rental License (approximately $250 initial, approximately $150 biennial renewal) and a City of Winter Haven Business Tax Receipt issued by the Building Division, with annual renewal due October 1. New accessory dwelling units are blocked from STR use for 10 years after construction.
The combined transient rental tax is approximately 12%: Florida state sales tax (6%), Polk County Tourist Development Tax (5%), and Polk County discretionary sales surtax (1%). Airbnb and Vrbo collect and remit Florida state sales tax and the Polk County TDT in most cases. There is no owner-occupancy or primary-residence requirement and no cap on annual rental nights.
Enforcement is rated low. Complaints route through Winter Haven Code Enforcement at (863) 291-5697. 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 STR registry, leaving the current framework intact into 2026.
Market Comparison
Winter Haven’s 60.3% April 2026 occupancy exceeds the U.S. STR annual median of approximately 55%, reflecting strong theme-park-driven year-round demand. The $223 ADR is close to the national median of approximately $220, slightly above, representing competitive pricing for a non-coastal Florida market.
Year-over-year revenue growth of 12.6% is the strongest in this batch, driven by the market’s growing vacation-villa economy tied to LEGOLAND expansion and the broader Lakeland-Winter Haven MSA, which is among the fastest-growing in the United States. The investability score of 89.3 and total market score of 87.2 are second-highest in this batch.
Among property managers, Evolve leads with 179 listings and 4,635 reviews (4.57 rating). RedAwning follows with 164 listings (4.24 rating). Vacasa holds 126 listings (4.42 rating). Top Villas has 111 listings (4.47 rating) and Master Vacation Homes holds 99 listings (4.73 rating). The combined top-5 count of 679 listings represents approximately 8.0% of the roughly 8,438 total market listings.
Frequently Asked Questions About Winter Haven, Florida
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