About Us

Mission Statement

Key West Residential Property Management is in business to provide the highest level of property management services to our customers. Our company is the most experienced in Key West with the most responsive and fast service.

Our sales division has expertise in helping you acquire quality investment properties. We know from our experience in property management what would be the best value for your investment based your needs.

Things to Know

  • Where the current real estate market is in Key West
  • How often the home prices come down
  • How much income is needed to make an investment property work

Meet the Team

Jaime Caballero » Broker / Owner

Jaime Caballero, a native of Key West, has been involved in property management since 1985. She started her senior year in high school working for her dad in the hotel business. Her father and mother's drive to work hard was soon contagious. After a short lived college career Jaime moved back to Key West. She was anxious to start working on her career.

Jaime was hired by Spottswood Family Trust and for the next 13 years did accounting and property management. In 2003 Jaime obtained her real estate license and went to work for Century 21 Prestige Realty Group for the next 6 years. Jaime's portfolio consisted of a 100 properties that were a mixture of long term rentals and vacation rentals.

In 2009 Jaime became a real estate broker and started her own company, Key West Vacation Properties & Realty. Later that same year she opened Key West Housekeeping Services to better serve her clients. In 2012 she opened Key West Residential Property Management in order to expand her long term property rental pool.

Jaime has 28 years experience in the real estate industry. Jaime is very active in NARPM and has worked with the organization to help promote best practices for property management.

National Association of Residential Property Managers (NARPM)
  • 2012 - present
  • 2016 NARPM Florida State Chapter President Elect
  • 2015 NARPM, MPM Candidate (Master Property Manager)
  • 2014 NARPM, RMP (Residential Management Professional)
NARPM Orlando Chapter Member
  • 2014 Regional Eastern Conference Committee Member
  • 2014 NARPM Membership Services Committee Member
  • 2014 Florida State Chapter Legislative Committee Member
National Association of Realtors (NAR)
  • 2003-present
RPAC Sterling Major Investor 2015
Florida Realtors
  • 2003-present
  • 2014 - 2016 Property Management Subcommittee
Key West Association of Realtors (KWAR)
  • 2003- present
  • 2016 MLS Committee Chair and Board of Directors
  • 2015 MLS Committee
Vacation Rental Managers Association (VRMA)
  • 2010 2014-present
Florida Vacation Rental Managers Association (FVRMA)
  • 2010 2011 2014
Key West Chamber of Commerce
  • 2010-present
The Lodging Association of The Florida Keys & Key West
  • 2010-present

Zillow Allstar Zillow Listings

Alexandria Caballero » Real Estate Agent

As a born and raised Conch from Key West, Alexandria has extensive knowledge of the Key West area. Her career in Real Estate began in 2008 working as reservation agent at Sunrise Suites Resort. Two years later, she moved to Pelican Landing as a reservation agent and later became on site manager of the resort.

After working for Key West Vacation Properties & Realty for 3 years, she decided to further her career in Real Estate and became a licensed Real Estate Sales Associate in 2011. Alexandria has successfully represented clients in real estate transactions while also managing Pelican Landing Resort. Whether representing a buyer or seller, her goal is to ensure that our clients are represented by someone who is on their side.

Alexandria is constantly researching websites such as the MLS to stay knowledgeable on the ever changing trends of the real estate market. She has attended numerous conventions to stay current on laws, technology, and other resources to help make herself the most efficient she can be. By taking these extras steps to better her familiarity with the real estate market, she can help our customers to find the best property to suit their needs.

If you are interested in buying or selling a little piece of paradise, feel free to call or come by to discuss your options.

National Association of Realtors (NAR)


Florida Realtors


Key West Assocation of Realtors (KWAR)

2011- present

Zillow Listings

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