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Leading Single-Family Property Management & Real Estate Services in Naples, FL
Stress-Free Property Management for Owners & Investors in Southwest Florida
Our experienced local team helps owners and investors manage both vacation and annual rentals while increasing cash flow, reducing vacancies, and protecting their assets.
Management Built on Accountability and Expertise
Woodruff Property Management and Real Estate takes personal pride in all of your long and short term property management needs.
Vacation rental check ins done in person. Woodruff Brokers meet every guest in person upon arrival.
Vacation rental check ins done in person. Woodruff Brokers meet every guest in person upon arrival.
Vacation rental check ins done in person. Woodruff Brokers meet every guest in person upon arrival.
Vacation rental check ins done in person. Woodruff Brokers meet every guest in person upon arrival.
Management Built on Accountability and Expertise
Shawn Cassel
Shawn Cassel has maintained his Broker licensing status for 25 years plus. He has managed real estate office for Coldwell Banker and Better Homes & Gardens with 140 plus agents under his supervision. He has extensive knowledge in contract negotiation & property management for Buyers, Sellers, Landlords and investors.
A Simple, Proven Property Management Process
At WoodRuff Property Management, we use a structured, hands-on approach to protect your property, minimize vacancies, and maximize long-term returns. From marketing and tenant placement to maintenance and financial oversight, every step is handled with professionalism, transparency, and attention to detail.
Our team manages the day-to-day operations so you do not have to. With qualified tenant screening, reliable vendor coordination, and clear reporting, we give you complete visibility and confidence while delivering a truly stress-free ownership experience.
Property Management Solutions for Every Type of Owner
We work with a wide range of property owners, from individuals renting a single home to investors managing multiple properties. Our services are tailored to your goals, your level of involvement, and your investment strategy so you always receive the right level of support.
Whether you live locally or out of state, we provide consistent communication, trusted local expertise, and dependable management. The result is better tenant experiences, protected assets, and stronger long-term performance for every property we manage.
Our team manages the day-to-day operations so you do not have to. With qualified tenant screening, reliable vendor coordination, and clear reporting, we give you complete visibility and confidence while delivering a truly stress-free ownership experience.
Got Questions? We Have Got Answers
Everything you need to know about working with WoodRuff Property Management.
1. What services do you provide?
We specialize in full-service property management for vacation and annual rentals, supporting owners with leasing, maintenance, and ongoing oversight.
2. How do you screen tenants?
vacation and annual rentals, supporting owners with leasing, maintenance, and ongoing oversight.
3. How do owners receive payments and reports?
Owners receive rental payments via secure direct deposit and can access monthly financial reports, statements, and documents anytime through the online owner portal.
4. Who handles maintenance and repairs?
We coordinate all maintenance and repairs through our trusted network of licensed vendors and contractors, ensuring work is done promptly and professionally. Owners are kept informed and must approve any major expenses per the management agreement.
5. How do I get started?
Getting started is simple.
Contact our team through the website or by phone to schedule a consultation. We’ll discuss your property, goals, and expectations, then recommend the best management or real estate solution for you.
What Our Clients Say
Real experiences from property owners and tenants who trust WoodRuff Property Management.
Melissa Di Giacomo
I contacted Woodruff Property Management after finding them here on Angie’s list. I scheduled a time for Troy to come out and provide me with an estimate. Troy showed up on time and provided me a professional proposal complete with rent comparables and a partial list of other properties under his management. I was a little skeptical at first because of their upfront fees and the monthly costs when compared to some other property management companies but in the end, their professionalism & their guarantee sold me.
Betsy
Hi Andrew, I wanted to send you an email and tell you what a difference it has been working with Geoff…. He is always available and gets back to me in a timely manner- there is NO BS. I feel that he is looking out for me as the client and helping me to make the best decision when it comes to my property. I wanted to let you know that I think he has been a great addition to your team and also am thankful for him stepping in and taking over my property. Thank you – hope you are well.
Tom Van Ness
Dear Patricia… I did speak to the potential client of yours that owns a condo that she cannot sell and would like to rent out. I gave you a glowing reference and told her I would not anyone else to manage our property other than you. I also told her you do not “nickel and dime” us to death like other companies do. She said she is moving to Africa and needs someone she can trust since she is moving so far away. I still cannot believe how you have collected the rent on our rental property so efficiently and on time compared to the prior property management company we had.