From messaging guests to managing cleaners to keeping your pricing competitive, successfully managing a vacation rental takes experience, considerable organizational skills, and time.
So turning to a property management company could be a sensible option. But how much can you really trust a third party with your properties? How hard will they work to protect your business interests? What hidden costs could you encounter?
These are just some of your very legitimate concerns when looking for a vacation rental management solution, and why we’ve spoken with Terry Whyte for fascinating insights, learned from his 30+ years as a short-term rental (STR) property manager in southern Florida.
By reading this article:
- You’ll learn how to choose the right property management company, and the questions to ask before contracting one.
- We look at four of the best vacation rental management companies in Florida.
- And we look at the hands-on approach that will keep you in full control over your business, and what tasks you can automate to cut out hours of work.
How to choose a short-term rental management company
You’ve invested in a beautiful short-term rental property, and now you want a hassle-free way to maximize your returns while your guests have an unforgettable stay. While opting for a short-term rental management company may seem like a good choice, there are a number of key issues to keep in mind.
We asked Terry Whyte from Anna Maria Island Beach Rentals to share his advice on how to choose the best STR management company for your business. Terry manages over 45 properties on Florida’s Gulf Coast and has more than 30 years of experience in the business.
He recommends the following as crucial areas of research and comparison when selecting the right STR property management company:
- Financial records
- Insurance coverage
- Transparency in commission fees
- Distribution strategy
- Metrics and KPIs
1. Financial records
Whether you’re moving from one property management company to another or if you’re new to the vacation rental market, Terry recommends reviewing at least two years of financials. He says, “Property management companies advertise promises with data that may not be relevant. So the first thing you should do is ask for financials.”
This will help you identify if:
- The company is a legitimate, well-established, and financially stable business
- You’re in good hands based on the company’s operational efficiency, revenue growth, and profitability
- The company can fulfill its commitments, like timely payments, property maintenance, and effective marketing strategies
2. Insurance coverage
“Natural calamities like hurricanes and floods are synonymous with Florida. And the biggest problem is that no insurance company wants to insure any property here. The insurance for the condo I own goes up by 25% every year—who knows, next year it could be 50%,” says Terry.
So, you need to be careful when checking if the property management company has adequate insurance coverage to protect against accidents or injuries occurring on your property and damages caused by tenants or third parties.
You should:
- Request a certificate of insurance (COI)
- Verify the information in COI with the insurance provider
- Consult with an insurance professional
- Request updated COIs periodically
Pro tip: Hostfully integrates with the following guest screening and insurance tools for short-term rentals:
These tools automate ID verification, check past reviews, run background checks, take deposits, and integrate with your centralized tech stack via Hostfully, so you can handle guest data legally and be alert to any risks. |
Transparency in commission fees
Terry warns that most property management companies in Florida aren’t upfront about their commission rates and other fees. He says, “They often won’t tell you the commission rate and the actual costs. For example, 100% of people pay for reservations with a credit card. So is the property management company charging you for the 3% credit card fees?”
Terry suggests looking out for additional fees like:
- Professional photography fees
- Copywiritng fees
- Pet fees
- Cleaning fees
- Administrative or management fees
4. Distribution strategy
On the need for wide channel distribution, Terry was adamant. “I can almost 100% predict the strength of a company by their distribution. Most property management companies advertise only on Airbnb and Vrbo—and this could get you killed,” Terry warned.
“You need to have a presence globally, especially with the market saturation—Expedia, Booking.com, Hopper, and HomeToGo are all channels you should be looking at, for example.”
Having a global presence helps you reach more travelers and get more bookings. A good property management company will also have an effective search engine optimization (SEO) and search engine marketing (SEM) strategy. Check how the company optimizes your listing. This way, you’ll know if you’re reaching your target audience.
Pro tip: Hostfully lists your properties across major listing sites like:
So with Hostfully, you can maximize your reach, bulk edit your listings, and eliminate double bookings. |
5. Metrics and KPIs
The occupancy rate and average daily rate (ADR) show how well your business is doing. Terry says, “You have to have those financials that we talked about. Does the property management company you choose have an occupancy rate of 80 or 90%? Or is it more like 50%?”
Terry says he pulls these key data points while onboarding property owners. He also showcases his tech stack and the revenue management tools he uses to adapt to market conditions and keep performance up.
Other key performance indicators (KPIs) to consider include:
- Revenue Per Available Room (RevPAR)
- No. of repeat bookings
- Length of stay (LOS)
- Average bookings for each channel
Questions to ask during the research phase
Before you commit to a short-term vacation rental management company, you need to ensure it’s “the one” for you. So, to help you play detective, we’ve compiled a list of questions you should ask:
- What channels do you market listings on?
- Who picks up the costs of photography and listing creation, credit card processing, and operations like cleaning and linens?
- What’s your occupancy rate throughout the year?
- What’s your ADR?
- Can you show me your last two years of financials?
- What’s your tech stack for managing bookings, payments, and reporting?
- What types of properties do you manage, and do you have any specialized expertise in managing properties like mine?
Channel your inner Sherlock Holmes to gain valuable insights into the company’s approach, capabilities, and track record to make an informed decision.
Best vacation rental property management companies in Florida
See our picks of the best vacation rental property management companies in Florida based on our criteria—professional-looking website, wide channel distribution, fees, and awards or recognition they’ve received:
- Anna Maria Island Beach Rentals: Best dedicated owner service and use of technology
- Casiola Vacation Homes: Best for global partnerships
- 10 Stars Property Management: Best for 3D virtual tour of your property
- Magical Stays: Best guest support
Anna Maria Island Beach Rentals: Best dedicated owner service
Source: Anna Maria Island Beach Rentals
Run by Terry and his wife Sandy, Anna Maria Island Beach Rentals manages properties on Florida’s Gulf Coast. They bought their first condo in 1995, and since then, have expanded their portfolio to over 45 properties. They were awarded the “Top Rental Property” award for two years running from TripAdvisor and FlipKey.
Terry also mentions that their paid occupancy is 71%, and their ADR is 39% higher than competitors. They use a powerful tech stack for dynamic pricing and revenue management that helps them achieve these results for their clients.
Services offered
- License and permit assistance
- In-house revenue management
- Accounting
- Reporting and taxes
- Transparent updates with automatic notifications
How does it fair against our checklist?
- Website: The website is very user-friendly with eye-catching photography, dynamic map, easy property search, and live chat for guests—plus useful information for owners.
- Wide channel distribution: They partner with 100+ largest booking websites like Airbnb, Vrbo, Expedia, and Booking.com.
- Pricing: Anna Maria Island Beach Rentals doesn’t charge property owners any additional or hidden fees—so no linen fees, vendor fees, management fees, or start-up fees. You can also get a free rental property income projection.
Casiola Vacation Homes: Best for global partnerships
Source: Casiola Vacation Homes
Casiola Vacation Homes is a leading vacation rental management company in Miami and Orlando. It was awarded the Best Marketing Campaign Award at the VMRA Excellence Awards 2022 and the Destinationaire Award 2022. Plus, it offers myCasiola, a real-time property dashboard for homeowners so you can follow up on guest reservations, add bookings, and manage bills.
Services offered
- Property care
- Marketing and design
- 24/7 guest support
- Dynamic pricing
- Financial reporting
How does it fair against our checklist?
- Website: Casiola has an impressive-looking website that showcases their services, awards received, and myCasiola—a real-time property dashboard that keeps you updated on the events in your property, lets you follow up with guests, add bookings, and manage documents.
- Wide channel distribution: They partner with the largest booking websites like Vrbo, TripAdvisor, HomeAway, Airbnb, and Booking.com. Plus, Casiola partners with 500,000 travel agents across the globe, running marketing campaigns on social media, search engines, and email marketing.
- Pricing: On the website, Casiola states that it takes a 20% commission fee with no linen fees, vendor markups, or management fees.
10 Stars Property Management: Best for 3D virtual tour of your property
Source: 10 Stars Property Management
Located in Pinellas Park, Florida, 10 Stars Property Management has recently moved into the vacation rental space. It was voted for ‘2022 best property management’ by expertise.com. What sets this company apart is the virtual 3D tour of your property which helps guests experience your properties in a fun, interactive way pre-booking.
10 Stars Property Management is also a member of the National Association of Residential Property Managers, Multiple Listing Service, and the Greater Tampa Association of Realtors.
Services offered
- Full home inventory
- House manual and digital guide
- Cleaning and maintenance supervision
- Owner block dates
- Assistance with taxes and permits
- Local booking team
How does it fair against our checklist?
- Website: The website is very professional and provides a thorough breakdown of its house rules and policies, but it’s geared toward long-term rentals, with the ‘Book here for your next vacation’ button taking the user directly to its Airbnb page.
- Wide channel distribution: 10 Stars advertises your property on Airbnb, Vrbo, and its direct booking website, and it provides custom-written, keyword-focused descriptions to help your listing stand out.
- Pricing: 10 Stars offers complete property management services for $49 per month, and it advertises on its homepage that there are no hidden fees, upcharges, or lock-in contract.
Magical Stays: Best guest support
Source: Magical Stays
Magical Stays is ideal for condos and homeowners across Orlando, Kissimmee, Davenport, and near Disney. The company provides pet-friendly vacation rentals, offers round-the-clock guest support to respond to new reservation inquiries, and uses automation to respond to standard inquiries immediately.
Services offered
- Cleaning and inspection
- Pest control
- Pool cleaning and maintenance
- Landscaping
- Property maintenance
- Administration
How does it fair against our checklist?
- Website: Filled with colorful imagery of young families enjoying Orlando’s theme parks, the website is focused on selling unforgettable experiences and offers tons of insights into the attractions, restaurants, and shopping alongside user-friendly search and booking for guests.
- Wide channel distribution: Magical Stays markets your properties across major listing sites like Airbnb, Booking.com, Expedia, TripAdvisor, and Vrbo. They also run frequent email and Facebook campaigns across their database of over 10,000 past guests to drive repeat bookings.
- Pricing: Magical Stays states that there are “no monthly management fees,” “no cleaning fees on company bookings,” and “no monthly escrow payments,” and you can fill in an online form to receive a “free rental evaluation.”
Or, manage your vacation rental independently with automation
So, when should you hire a short-term rental management company? If you’re looking for a hands-off approach or don’t have the time to manage your rental, these companies are ideal. But property management companies charge a percentage of your rental income, ranging from 10% to 40% or more, depending on the services they provide.
If you want to cut out those commissions, a property management system (PMS) can help you navigate tasks easily and maximize your revenue.
For example, Hostfully’s booking pipeline manager and digital guidebooks improve your guest experience by giving visitors recommendations and tips, while its features for automation save you time and eliminate human error.
Source: Hostfully
Here’s how Hostfully can help automate your vacation rental business process:
- Booking pipeline. You can get visibility into your bookings and lead status, assign them to team members, and automate the guest journey.
- Digital guidebooks. You can create browser-based guidebooks to upsell services, answer guest questions, provide recommendations, and improve the contactless experience.
- Channel manager. Hostfully’s channel manager gets your vacation rental properties visibility on multiple platforms, including your direct booking website, for maximum exposure.
- Booking engine. Drive direct bookings with intuitive websites using readymade templates or embed the direct booking widget on your existing website.
- Automated messaging. Set up automated messaging with message templates and triggers to minimize the time you spend on guest and staff communication.
- Accounting and reporting. Hostfully integrates with QuickBooks and Ximplifi so you can sync your expenses and payments and monitor your financial health in one place.
What’s right for your vacation rental: Property management company or PMS?
Scaling your vacation rental business in Florida isn’t just about owning a beautiful property — it’s about finding the right management solution.
Property management companies can take care of every aspect of running your rental, from collecting rent to guest screening and maintenance. But you won’t have the same control over who stays at your property. Plus you could be charged with hidden costs that aren’t made clear at the time of signing on the dotted line.
Meanwhile, with an end-to-end PMS, you can automate repetitive tasks, create a direct booking site in minutes, and take hours off your weekly workload.
