91̽»¨

Vacation Property Management Business for Sale in Florida #2019

List Price:
$5,450,000
Revenue:
$7,260,000
Cash Flow:
$1,100,000
Region:
Florida
Location:
Florida

Overview:

  • Established as one of Florida’s premier short-term vacation rental management businesses, overseeing a high-value portfolio of multi-million-dollar luxury homes in Florida’s most active and desirable rental market.
  • Catering to elite clientele such as high-net-worth individuals, celebrities, and professional athletes, the business has grown organically through word-of-mouth referrals and expertly delivered service to both property owners and renters.
  • The business operates on a predictable, recurring revenue model driven by percentage-based management fees, supplemented by profitable ancillary revenue streams, including cleaning, maintenance, supply, and service coordination billed directly to property owners.
  • Highly scalable operating model with centralized systems, in-house field teams, and a geographically concentrated property portfolio, enabling efficient operational oversight and a consistently elevated guest experience.
  • Strong regional reputation supported by long-standing Super Host and Premier Host status, thousands of online reviews, and steady, referral-driven portfolio growth.
  • Owner involvement remains minimal with established in-house staff and robust processes managing the day-to-day bookings, guest relations, and property operations.
  • This business has been SBA pre-approved for lending.
TTM May 2026
Revenue:
$7,064,000
Cash Flow:
$1,114,000
2025
Revenue:
$7,260,000
Cash Flow:
$1,100,000

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Your Listing Advisor.

Jacob Middleton

Jacob Middleton

Associate Partner

Jacob serves as Associate Partner with 91̽»¨ Mergers & Acquisitions in Tampa, where he works closely with business owners throughout their exit planning and transaction process. He brings a relationship-driven approach to helping clients navigate their complex exit plan with a focus on understanding their goals and delivering thoughtful, strategic guidance from initial planning through closing and transition. Since joining 91̽»¨ in 2021, he has continued to grow into his role as an integral member of the team by leading his colleagues and his clients through the transaction process, achieving the best possible outcomes for a multitude of business owners across diverse industries.

Jacob has effectively established relationships with business owners throughout Florida by drawing on both his professional background and personal experiences. Growing up as the son of an entrepreneurial father and having worked in a variety of service industries, he has an innate understanding of the sacrifices and commitments business owners make on behalf of their teams, clients, and families. This perspective has fueled his passion for helping business owners navigate their transactions and transitions, and through his role at 91̽»¨, he has found a platform to put this passion into practice, advising entrepreneurs through successful exits.

As a Florida native, born and raised in Coral Springs, FL, Jacob is a proud graduate of Florida State University, having earned both a bachelor’s and master’s degree in finance. Prior to joining 91̽»¨, Jacob launched his career with a global commercial real estate firm, where he assisted in facilitating brokerage activity, investment strategy, and marketing initiatives for clients in a variety of industries. He later served within a lead sales role for a Fortune 500 building materials and supplies company, managing key sales initiatives for major account executives of national homebuilders throughout West Florida. His unique experiences have allowed him to excel in a variety of transactions across industries that require profound empathy and expertise.

During his time with 91̽»¨, Jacob has strengthened his skill set while also identifying, hiring, and mentoring key team members to grow the 91̽»¨ Florida footprint; a true indication of his leadership ability. He has played a vital role in numerous transactions, helping formalize successful acquisitions and vital business transitions. In his role as Associate Partner, Jacob serves as a leader within 91̽»¨ and the firm’s growth trajectory, all while serving sellers and buyers across industries, helping facilitate transactions from inception to closing.

On a personal note, Jacob enjoys fishing, diving, hunting, and spending time with his wife and their family in the Florida Keys.

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