Compare 7 local companies in Key West (6 with an office in the city, 1 that serves the area). Pick up to 3 and send one free quote request.
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Your request goes to the managers you pick, or to the 3 top Best match managers in Key West. You see who before you send.
Top rated
Highest Best match score
Most reviewed
36 Google reviews, 4.6★
Longest established
20+ years in business
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.
302 Southard St Ste 102, Key West, FL 33040
The Watkins Group is a Key West real estate and property management company that has managed long-term rentals and commercial properties from Key West to Key Largo since 1988, and also handles sales.
Review summary: Reviewers often describe a knowledgeable, proactive team that helps clients buy, sell and find homes in Key West.
323 Fleming St, Key West, FL 33040
Key West Residential Property Management is a Key West company whose staff has over 30 years of local experience managing long-term rentals in condos, townhomes, apartments and office properties, with screening, rent collection and maintenance.
In their words: “We conduct extensive screening on all tenants and handle everything from moving your qualified tenant into their new home, to rent collection, to handling maintenance issues.”
Review summary: Owners often describe responsive, knowledgeable service and good tenant placement over many years.
3706 N Roosevelt Blvd Ste 207, Key West, FL 33040
Real Estate Management of Key West has an office in Key West and offers real estate sales, full property management, home watch, HOA and condo association management, and hurricane preparation.
Review summary: Reviewers mention responsive, trustworthy service, both from agents on sales and from managers caring for homes.
Historic Key West Annual Rentals is a locally owned Key West company, operating since 2004, that manages annual and long-term rentals with maintenance, marketing and inspections.
In their words: “Whether you're a tenant, a single property owner, or seeking a property management company to oversee multiple properties, we are here to help.”
Review summary: Reviewers often describe a knowledgeable, responsive agent who helps them find a rental home.
Serves the Key West area · no public office address, so no map pin
BDM Property Solutions serves the Key West area and the Florida Keys, managing rental homes, condos and HOAs with tenant placement, rent collection, maintenance, community association management and real estate services.
In their words: “We handle tenant placement, rent collection, maintenance, and tenant transitioning.”
Pelagic Property Management, formed in 2015, manages residential, multifamily, commercial, office, storage and retail properties in Key West and the Lower Keys, including affordable housing, with leasing and rent collection.
In their words: “From leasing agreements and marketing properties to background/credit checks, we provide all the right services in an efficient and professional manner.”
1075 Duval St C19, Key West, FL 33040
Key West Rental Company is a real estate and property management group in Key West that places qualified tenants in long-term rentals across Key West and the Florida Keys.
No company matches all of these filters.
The map needs JavaScript. Every company's address is in its card.
Pins show office addresses; numbers match the Best match order. Companies that don't publish an address are listed as "Serves the Key West area" and get no pin.
Get the latest rental and real estate data on the Key West market. We update these charts with the latest data on the 22nd of each month.
Rents in Key West are $108 below the Monroe County typical.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed. Data through September 2026.
Rent rose in 4 of the last 12 months: −$387 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.
Key West's typical asking rent is $108 (2.9%) 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.
Key West is number 2 of 2 cities in the county by typical asking rent.
Cities with at least 13 months of Zillow data. 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.
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 |
|---|---|---|---|
| Key West | $3,563 | −9.8% | 7 |
| Naples | $2,602 | +2.3% | 43 |
| Coral Gables | $3,345 | +3.2% | 14 |
| Bonita Springs | $2,786 | +0.5% | 12 |
| Doral | $2,881 | +0.5% | 11 |
| Estero | $2,594 | +3.1% | 5 |
| Miami | $2,965 | +1.3% | 108 |
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, Monroe County, FL. Used to set Housing Choice Voucher (Section 8) limits.
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Compare the 7 property management companies in Key West, Monroe County. Tick up to 3 to see them side by side, then request free quotes from all of them in one step.
Zillow's typical asking rent in Key West is $3,563 (September 2026); −9.8% over the past year. About 50.8% of homes in Key West are rented, and the rental vacancy rate is 13.1% (Census, 2020-2024).
We list 7 property management companies in Key West, FL: 6 with an office in the city and 1 that serve the area from elsewhere or without a public office address.
Zillow's typical asking rent in Key West was $3,563 a month in September 2026, −9.8% on a year earlier.
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.