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Jaime Caballero

O: 305-296-6667

Stay a day, a week or a lifetime......

If you are in the need of a vacation rental or have decided to move to Key West, let me help you. I am a native "conch"! I was born and raised in Key West. I have over 30 years experience in property management industry. I consider myself extremely knowledgable in investment property in Key West. I can recommend options of what property to buy that will best fit your investment and/or second home needs.

I have been a Broker since 2009 when started my own company, KWVPR. I have been a real estate agent since 2003 and a property manager since 1989. If you own a property in Key West and are interested in having your property managed, let me help you. If you are in need of a vacation getaway or have family coming into town, I can help. I have rooms, 1 bedrooms up to 4 bedrooms by the night. If you need a place to live I have long term rentals. If you need to buy or list a property, both my daughter Alexandria who is a real estate agent or I can help. Feel free to call us anytime and we can discuss your options.

Awards & Designations

National Association of Residential Property Managers (NARPM)
2012 - present

2015 NARPM, MPM candidate (Master Property Manager)
2014 NARPM, RMP (Residential Management Professional)
NARPM Orlando Chapter Member
2014 Regional Eastern Conference Committee Member
2014 Membership Services Committee Member
2014 - 2015 Florida State Chapter Legislative Committee Member
2016 2017 Day on Hill
2016 2017 State Conference Committee
2016 2017 National Legislative Committee
2016 2017 National Conference Committee
2016 2017 Florida State Conference Committee
2017 Florida State Chapter President
2017 2018 Investment Committee
2018 National Conference Committee Co Chair

National Association of Realtors (NAR)
2003- present
2016 2017 Governance Meetings DC
2018 -2019 Resort and Second Homes Committee
2019 Federal Technology Policy Committee
2020 - 2021 Single Family Investment Management

Florida Realtors
2014 -2021 Property Management Committee
2016 2017 Great American Realtor days
2015 2016 RPAC Sterling
2017 Resort and Second Home Specialist Breakout Group
2017-2021 Legislative Think Tank
2017-2019 2021 Public Policy Committee
2017 Insurance Breakout Group
2017 2020 Vice Chair Property Management Committee
2017-2021 Board of Directors
2017 Leadership Academy
2017 RPAC Golden R
2018 2021 Chair Property Management Committee
2018 Florida Realtor Party Coordinating Committee
2018 Fundraising Subcommittee
2018-2021 Board Leadership Forum
2018 RPAC Golden R President’s Circle
2019 REALTOR Party Member Involvement Committee
2019-2021 Convention Committee
2019-2021 Platinum R Hall of Fame
2021 Key Contacts Subcommittee
2021-2023 Public Advocacy Advisory Group
2022 Key Contacts Subcommittee Vice Chairperson
2022 Legislative and Regulatory Business Issues Breakout Group
2023 Key Contacts Subcommittee Chairperson

Key West Assocation of Realtors (KWAR)
2003- present
2015 MLS Committee
2016 MLS committee Chair and Board of Directors
2016 Tri Board Committee
2017 RPAC Chair and Board of Directors
2018 2019 Treasurer
2020 President Elect
2021 President
2016 - present Orlando Regional Realtor Association (ORRA)
2016 Gold Key Certification

Vacation Rental Managers Association (VRMA)
2010 2014 2015 2016

2010-present Key West Chamber of Commerce

2010- present The Lodging Association of The Florida Keys & Key West

Jaime Caballero
Office: 305-296-6667
Key West Vacation Properties & Realty
323 Fleming St
Key West FL 33040

Contact Me Now