About Historic Key West Annual Rentals
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.
Years in business from the company's website: “Since 2004, Historic Key West Annual Rentals has been one of the leading Annual Rental, Long-Term Rental and Property Management Companies in Key West.”
Written by our team from the company's Google listing and website.
What we checked
- Google listing open, checked October 2026
- Manages rentals for other owners (our property-manager check)
- Website read on November 4, 2026
- Newest Google review: June 25, 2026
Not checked by us
- Florida license records (coming soon)
- Fees and contract terms: ask for a written quote
- Insurance
- Service quality beyond Google reviews
No company pays to be listed or ranked. How we choose companies
At a glance
Services
- Maintenance
- Marketing
- Inspections
- Vacation rental management
Areas served
- Key West
From the company's website, checked November 4, 2026.
How they work with owners
- Inspections
- “We offer internal/external inspections as well as coordinate any vendor services, checking vehicles and mail pickup.” Source
Copied word for word from the company's website, read November 4, 2026.
Office and hours
1119 White St, Key West, FL 33040
| Monday | 9:00 AM – 5:00 PM |
| Tuesday | 9:00 AM – 5:00 PM |
| Wednesday | 9:00 AM – 5:00 PM |
| Thursday | 9:00 AM – 5:00 PM |
| Friday | 9:00 AM – 5:00 PM |
| Saturday | Closed |
| Sunday | Closed |
Hours from Google. Call ahead to confirm.
Google rating
Topics reviewers mention
- Ease of use 4
- Knowledgeable staff 4
- Fee 3
- Charge 3
- Security deposit 3
- Llc 2
- Cleaning 2
- Contract 2
- Teamwork 2
- Helpfulness 2
Source: Google. Newest review June 25, 2026. We show counts only, never review text. Read the reviews on Google
Questions about Historic Key West Annual Rentals
Where is Historic Key West Annual Rentals located?
Historic Key West Annual Rentals's office is at 1119 White St, Key West, FL 33040.
How long has Historic Key West Annual Rentals been in business?
Since 2004, about 22 years. Its website says: “Since 2004, Historic Key West Annual Rentals has been one of the leading Annual Rental, Long-Term Rental and Property Management Companies in Key West.”
How much does Historic Key West Annual Rentals charge?
Historic Key West Annual Rentals does not publish its fees on its website. Ask for a written quote that lists the monthly fee, leasing fee and any other charges.
Which areas does Historic Key West Annual Rentals serve?
Its website lists Key West.
What does Historic Key West Annual Rentals manage?
Services: maintenance, marketing, inspections and vacation rental management. From the company's website.
What do Google reviewers say about Historic Key West Annual Rentals?
Historic Key West Annual Rentals has a 4.3 rating from 17 Google reviews. Reviewers often describe a knowledgeable, responsive agent who helps them find a rental home.
How do I get a quote from Historic Key West Annual Rentals?
Use Request a free quote on this page. Your request goes only to Historic Key West Annual Rentals. It is free and there is no obligation.
Compare with other Key West managers
The top Best match companies in Key West. Tick up to 3 to compare and request quotes together.
Historic Key West Annual Rentals
This company
Key West's typical asking rent was $3,563 in September 2026 (−9.8% in a year, Zillow). See the Key West rental market