Compare 5 local companies in Winter Haven. Pick up to 3 and send one free quote request.
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Top rated
User Recommended
Most reviewed
179 Google reviews, 4★
Picked by our rules (rating adjusted for review count, number of reviews, years in business), not paid placement.
Tick Compare on up to 3 companies to see them side by side and request quotes from all of them at once.
3100 Cypress Gardens Rd suite a, Winter Haven, FL 33884
Pro X Property Management - Swain Group is a Winter Haven company founded in 2022, managing single-family homes, apartments and multi-family properties in Winter Haven, Lakeland and Polk County.
In their words: “Serving the area of Polk County, FL, our dedicated and hard working team is here to help you and your rental property thrive.”
Review summary: Reviewers, mostly tenants, often describe helpful, professional staff who respond quickly.
403 1st St S, Winter Haven, FL 33880
Property Management of Polk has an office in Winter Haven and manages rental properties in Polk County, with property management and rental listings.
Review summary: Reviewers often mention attentive, communicative managers who care about tenants and owners, though one cited a canceled appointment.
331 W Central Ave Ste 240, Winter Haven, FL 33880
Real Property Management Lakeside is a Winter Haven office of the Real Property Management franchise, managing residential rentals in Polk County with screening, leasing, maintenance, rent collection and inspections.
In their words: “We offer professional rental property management services for real estate investors and property owners throughout Polk County and nearby areas.”
Review summary: Most reviewers mention a smooth rental process, responsive staff and helpful, knowledgeable advice.
Village Realty has an office in Winter Haven and has managed single-family rental homes in the greater Winter Haven area since 1974, handling marketing, tenant screening, rent collection, inspections, maintenance, evictions and an owner portal.
In their words: “Call us today to learn how our team can help you manage your rental or find you a home to rent in the greater Winter Haven area.”
500 Orchid Springs Dr, Winter Haven, FL 33884
Stambaugh is a Cypress Gardens community association management company serving condos, HOAs and Community Development Districts in Orchid and Winter Haven, with accounting and full-service rental property management.
In their words: “We serve Community Development Districts, Homeowners and Condominium Associations, and we offer Full Service Property Management for all your rental needs.”
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Pins show office addresses; numbers match the Best match order. Companies that don't publish an address are listed as "Serves the Winter Haven area" and get no pin.
Get the latest rental and real estate data on the Winter Haven market. We update these charts with the latest data on the 22nd of each month.
Rents in Winter Haven are $128 below the Polk County typical.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed. Data through September 2026.
Rent rose in 8 of the last 12 months: +$37 in all since Oct 2025.
Green: rent went up that month. Grey: it went down.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed. Data through September 2026.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed. Data through September 2026.
Winter Haven's typical asking rent is $128 (7.1%) below the county. The gap is shrinking compared with a year ago.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed. Data through September 2026.
Winter Haven is number 8 of 9 cities in the county by typical asking rent.
Cities with at least 13 months of Zillow data. Left out (too few months): Eagle Lake, Lake Alfred, Polk City. Linked cities have their own page.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed, 1-year change. Data through September 2026.
Rents here usually rise most in April, May and September, so those are good months to list your rental.
Average change from the month before, 11 years of data.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed. Data through September 2026.
Past growth, not a forecast. Rents can go down as well as up. Your own rent depends on the home, its condition and the lease.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed. Data through September 2026.
| City | Typical rent | 1 year | Managers |
|---|---|---|---|
| Winter Haven | $1,686 | +2.2% | 5 |
| Auburndale | $1,741 | +0.3% | 3 |
| Davenport | $1,978 | +1.2% | 8 |
| Lake Wales | $1,512 | −0.2% | 3 |
| Lakeland | $1,687 | +1.1% | 21 |
| Plant City | $1,766 | −3.4% | 7 |
| Kissimmee | $1,926 | +0.3% | 20 |
Source: Zillow Observed Rent Index (ZORI), typical asking rent, data through September 2026. Managers listed: our directory, October 2026.
Source: U.S. Census Bureau, American Community Survey 5-year estimates, 2020-2024.
Source: U.S. Department of Housing and Urban Development, Fair Market Rents for fiscal year 2027, Lakeland-Winter Haven, FL MSA. Used to set Housing Choice Voucher (Section 8) limits.
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Compare the 5 property management companies in Winter Haven, Polk County. Tick up to 3 to see them side by side, then request free quotes from all of them in one step. Highly rated managers based nearby, in Lake Wales and Poinciana, are listed below the local companies.
Zillow's typical asking rent in Winter Haven is $1,686 (September 2026); +2.2% over the past year and +17.7% over five years. About 36.3% of homes in Winter Haven are rented, and the rental vacancy rate is 3.7% (Census, 2020-2024).
We list 5 property management companies in Winter Haven, FL.
Zillow's typical asking rent in Winter Haven was $1,686 a month in September 2026, +2.2% on a year earlier.
Over the 11 years Zillow has tracked, asking rents here have risen most in April, May and September. Listing in those months can help, but every property is different.
Fees depend on the company, the property and the services you need, and few companies publish them. Ask for a written quote that lists the monthly fee, leasing fee and any other charges. You can request quotes from up to 3 managers at once on this page.
The default order, Best match, uses each company's Google rating adjusted for how many reviews it has, so a 4.8 rating from 100 reviews ranks above a 5.0 from 2. Companies with no Google reviews yet are listed after every rated company. No company can pay for its position.
Yes. Requesting quotes is free for property owners and there is no obligation to hire anyone.