Compare 5 local companies in Windermere. Pick up to 3 and send one free quote request.
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Top rated
Highly Recommended · 100+ reviews
Most reviewed
144 Google reviews, 4.1★
Picked by our rules (rating adjusted for review count, number of reviews, years in business), not paid placement.
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9100 Conroy Windermere Rd Suite 200, Windermere, FL 34786
West Orlando Property Management Realty is a company based in Lake Butler offering tenant screening, rent collection, maintenance, leasing and marketing for rental owners in Orlando, Windermere and Apopka.
Review summary: Most reviewers mention attentive care for tenants, quick responses and a smooth process.
9100 Conroy Windermere Rd Suite 200, Windermere, FL 34786
Icon Realty Associates is a Windermere-area real estate company, listed in Lake Butler, offering property management, leasing and sales in Orlando and Windermere, with over 1,000 homes sold and rented in more than 15 years.
In their words: “Whether you’re seeking a home, aiming to expand your portfolio, or require expert property management, we have you covered.”
Review summary: Most reviewers describe professional, responsive agents with good market knowledge, mostly for home sales.
13790 Bridgewater Crossings Blvd Ste 1080, Windermere, FL 34786
PMI Property Alliance is a Horizon West office of the Property Management Inc franchise, offering residential and commercial property management in the Orlando area, with tenant screening, leasing and accounting and reporting.
In their words: “PMI Property Alliance is a full-service real estate asset management company that provides professional Residential and Commercial services.”
Review summary: Most reviewers mention a kind, patient and responsive manager and an easy rental and move-in process.
13790 Bridgewater Crossings Blvd #1080, Windermere, FL 34786
RentCare Property Management is a Horizon West company that has placed tenants since 1993, managing single-family homes, townhomes and condos in Windermere, Winter Garden, Horizon West, Orange County and Lake County.
In their words: “We handle rent-ready preparation, ongoing property maintenance, and preventative repairs to keep your home in excellent condition and preserve its value.”
Review summary: Reviewers often describe a professional, responsive team with strong communication.
13506 Summerport Village Pkwy, Windermere, FL 34786
FL Villa Management has an office in Horizon West and serves the Four Corners area, handling tenant screening, rent collection, maintenance and repairs for rental owners.
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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 Windermere area" and get no pin.
Get the latest rental and real estate data on the Windermere market. We update these charts with the latest data on the 22nd of each month.
Rents in Windermere are $521 above the Orange County typical.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed. Data through September 2026.
Rent rose in 6 of the last 12 months: +$8 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.
Windermere's typical asking rent is $521 (27.0%) above 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.
Windermere is number 2 of 10 cities in the county by typical asking rent.
Cities with at least 13 months of Zillow data. Left out (too few months): Gotha, Oakland. 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 July, 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 |
|---|---|---|---|
| Windermere | $2,454 | +0.3% | 5 |
| Winter Garden | $2,352 | −0.5% | 21 |
| Clermont | $2,013 | −1.4% | 12 |
| Maitland | $1,960 | +4.1% | 3 |
| Winter Park | $1,852 | +2.7% | 19 |
| Apopka | $2,064 | +0.7% | 0 |
| Altamonte Springs | $1,588 | −0.2% | 12 |
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, Orlando-Kissimmee-Sanford, FL MSA. Used to set Housing Choice Voucher (Section 8) limits.
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Compare the 5 property management companies in Windermere, Orange 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 Celebration and Kissimmee, are listed below the local companies.
Zillow's typical asking rent in Windermere is $2,454 (September 2026); +0.3% over the past year and +14.0% over five years. About 4.4% of homes in Windermere are rented, and the rental vacancy rate is 22.4% (Census, 2020-2024).
We list 5 property management companies in Windermere, FL.
Zillow's typical asking rent in Windermere was $2,454 a month in September 2026, +0.3% on a year earlier.
Over the 11 years Zillow has tracked, asking rents here have risen most in April, May and July. 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.