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Anna Maria Island Vacation Rental Property Management

The premier vacation rental management company in Anna Maria Island. From trusted local property care and maximizing rental income, to transparent communication and 5-star guest experiences—we have you covered.

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Isn’t it time your second home was

Worry-free?, Making money?, 5-star rated?, Well-maintained?, Fully-booked?

SkyRun is the industry’s most trusted team of property managers. With decades of experience behind us, we know what it takes to stay ahead of the curve in the fast-paced vacation rental industry without sacrificing the personal care that homeowners need. When you put your second home in our hands, your vacation rental dreams can become a reality sooner than you think.

30%

Homeowners report earning up to 30% more after switching to SkyRun

2.4x

SkyRun properties are booked 2.4 times more often than the average listing on leading booking channels.

4.8

SkyRun properties average an industry-high 4.8 out of 5 stars in guest reviews

Local Ownership + National Reach

We’re a collective of independently owned and operated vacation rental businesses backed by a team of national experts.

You Don’t Have To Choose

Our unique combination of local ownership and national reach means homeowners no longer have to choose…

  • Between hands-on care and cutting-edge technology
  • Between having a relationship with your manager and strong revenue
  • Between low fees and quality service

The SkyRun Difference

We’re a local business, but we’re not a mom and pop shop. We’re national, but we’re not a mindless profit machine. We’re the best of both worlds.

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Unparalleled reputation
Listing & optimization on leading booking channels
Professional marketing
Efficient tech stack
Local business ownership
Cutting-edge revenue management
Straightforward contract terms
Easy onboarding process
User-friendly owner portal
Quick owner & guest response
24/7 guest support
Local regulatory expertise & guidance
Maintenance
Housekeeping
Premium guest amenities and services
Peace of mind
Skyrun Vacation Rentals
Full
Service
Basic
Service
The Competition
Small
Business
Big
National
Self-
Managed

Be Where the Guests are Looking and Booking

Homeowner Success Stories

Anna Maria: Soul Shine

3-Bedroom House

Bradenton: Sunset Oasis

3-Bedroom House

Bradenton: Royal Poinciana & 11 Palms

2-Bedroom Home & 4-Bedroom Home

Matt was very clear from the start and helped us build real expectations for our investment property. We’re pleased with how easy the process has been.

Paul & ClaireBradenton, FL

The entire process has been incredibly smooth, providing us with a true sense of peace of mind. From property management to timely payments, it’s been hassle-free. We couldn’t be happier with the service provided by SkyRun.

Melissa TaylorW. Bradenton, FL

SkyRun has done an amazing job with my beach condo. They pay attention to every detail and provide incredible service. They are super responsive and go way above and beyond. In just a very short time they have secured a large number of bookings for my unit. Exceptional company to work with and I highly recommend them.

Nan S.Sarasota, FL

Matt gave a realistic number and also hit that number. My properties have been renting solid. He’s been so good that I continue to buy houses to have him run.

NathanBradenton, FL
Your Local Team

Locally Owned and Operated In Anna Maria Island

Each SkyRun Vacation Rentals franchise is locally owned and operated in order to deliver superior service to homeowners and guests while actively engaging in the communities in which we operate. Because we operate a small number of rentals in our own backyard, we’re able to put time and personalized attention into each of them. That kind of service is just not possible with traditional, top-down rental corporations.

  • Enjoy a personal relationship with your manager, who is here to answer any and all questions about your home. We are here to create customized solutions to reach all your goals.
  • We live, work, and play here on Anna Maria Island. Our local team is just a stone’s throw away from your home and we will step in to help in any situation, anytime.
  • Our knowledge of local attractions and hidden gems allows us to provide guests with insider recommendations, enhancing their stay and increasing repeat bookings.

Matt Cooper, Owner

941-799-1128

matt.cooper@skyrun.com

Our Commitment to Homeowners

Cash

Say goodbye to being nickel and dimed, and say hello to more rental income with expert revenue management and powerful marketing. It’s easy to switch and we don’t have any onboarding fees.

Some management companies promise low fees then slam you with incremental surprise charges for lightbulbs, snow shoveling, and linens. SkyRun doesn’t believe in nickel and diming—you’ll get simple, straightforward terms on your contract with us so you’ll always know what to expect.

It doesn’t cost anything to get started with SkyRun. We make money only when you do: when we get your property booked.

We’ve cracked the code when it comes to pricing your property. Using a scientific approach powered by our national data set and local competitive intelligence, we’ll always price for the best returns on your investment, leaving no money on the table. With this approach, SkyRun homeowners report earning up to 30% more after switching to us.

Your property will not only be listed on the leading online booking channels, but will be optimized to perform well against other similar homes. In fact, SkyRun managed properties are booked 2.4 times more often than the average listing on leading booking channels.

Being part of a franchise, each SkyRun location is equipped with a highly efficient integrated tech stack to run our business. This software helps keep our overhead low, a savings we pass along to our homeowners.

We collect and pay your state and local taxes for nightly rentals. We also organize and prepare your year-end tax documents.

Care

As a local business, our reputation means everything to us. We offer 100% owner satisfaction and you are never just a number to us – you’re our neighbor. Plus, your guests will always be taken care of!

Our preventative maintenance approach utilizes proactive inspections, routine service, and smart tech to keep your property in excellent condition. Are you looking to retire in this home? We’ll make sure it is ready when you are.

In between stays, our professional team of housekeepers complete a thorough cleaning and restocking process to leave your home sparkling before the next guest arrives.

Homeowners stay happy with SkyRun because we go above and beyond to meet their needs. If you aren’t satisfied, we aren’t either–and we’ll work to make it right.

There’s no reason why guests shouldn’t feel pampered in a vacation rental. We provide high-quality linens, towels, and amenities and our team will restock all guest disposable supplies in between stays.

SkyRun is committed to taking the worries out of vacation rentals for both homeowners and guests. Ask us about our solutions to keep your property safe and protected from liability while you rent it out.

Happy guests power positive reviews—the #1 most important factor in influencing future bookings. On top of providing 24/7 guest support, we provide local recommendations and discounts to enhance the guest experience. The results? SkyRun earns an industry-high guest rating of 4.8 stars out of 5 across our locations and has over 30 thousand 5-star reviews to date.

Communication

You’ll have an open line of communication to our team when you need us and be able to access your owner portal 24/7. No running in circles, we get right back to you each and every time.

You’ll know your property manager and have a direct line of communication to them when you need them. They’ll live near your home and can be there in a heartbeat should they need to be.

Keep all of your home’s information at your fingertips with our easy-to-use owner portal. From here, you can see, make, and manage your reservations; check your home’s KPIs and customize which metrics you want to track; and view and download your monthly statements, 1099s, and annual reports.

From before the booking all the way through and after checkout, we’re in communication with your guests to ensure they have a smooth and pleasant stay. To make it easy, we’re available to them via phone, email, and text 7 days a week.

We’re experts in local regulations surrounding short term rentals. Things are changing fast, and we know what homeowners need to do to maintain the proper permits and licenses as a vacation rental. We will guide you through the process to ensure your investment property is in full compliance with the law.

Areas We Serve

We serve homeowners within Anna Maria Island, Palma Sola, and Bradenton with short term rental management solutions they can trust.

Frequently Asked Questions

Our local ownership model allows us to provide exceptional hands-on service and care to our homeowners, while our national network empowers us to stay on the cutting-edge of the industry. SkyRun truly is the best of both worlds between the big, impersonal brands and the homespun (often old-school) mom and pop shops.

SkyRun is a collective of local franchise owners who leverage SkyRun’s technology, brand, and overall systems to 1) Own and operate their own vacation rental business, 2) Provide full-service property management for your home, and 3) Deliver an unmatched guest experience for your home’s visitors.

No! You can decide how many days you’d like to spend in your home, and how many days you’d like to rent out. We can adapt to your wants and needs as a second homeowner. The only limits are those imposed by any state or county regulations that may be relevant to your home.

We understand that every property is unique. Contact our team for a free detailed analysis on your home which will show a clear breakdown of all expected revenue and costs. This process allows us to be as straightforward as possible, a policy we pride ourselves on, so our homeowners never feel nickel and dimed.

Here’s how we maximize your property’s revenue: 
  1. Your property will be listed and optimized across every single top booking channel, leading to 2.4 times more bookings compared to average listings. Our expertise in booking channel algorithms ensures top visibility for your property.
  2. We use a data-driven approach to pricing, ensuring your property is always set to capture the highest possible returns. We combine advanced software with local insights and personalized touches to keep your property optimally priced, attracting more bookings.
  3. We deliver five-star guest experiences, from exceptional cleaning standards to 24/7 support. This high level of service earns top reviews and enhances your property’s ranking, enabling us to increase your rates.
As a result, SkyRun homeowners often see up to 30% more revenue after partnering with us.

You’ll have access to an easy-to-use owner portal. Here, you can view, create, and manage your reservations. The portal also provides real-time insights into your home’s key performance indicators (KPIs), so you’re always informed about its performance. Additionally, you can access and download your monthly statements, 1099s, and annual reports.

Call us at 941-241-3054  or email us at kaitlyn@skyrun.com We look forward to unlocking your home’s potential together!

Realtor Partnerships

A vacation rental expert in your back pocket

SkyRun is proud of our relationships with realtors. Leverage our extensive knowledge of the ins- and -outs of vacation rental ownerships to help your clients achieve their dreams, and help you close more deals.

Learn more

Ready to get Started?

Call us at 941-799-1128 or fill out the form at the top of this page, and we’ll send you more information.

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