Siesta Key property management company
More of our rentals are here than anywhere else.
That covers condos and houses. The office is on the mainland at 5774 S. Tamiami Trail, across the bridge, and it's open seven days a week.
Property owners created this company for property owners. We put hospitality first and use advanced marketing and dynamic pricing to maximize owner revenue.
Some owners call us a rental agency and some call us property managers. On Siesta Key it's the same job.
We manage from Lido Key down to Venice.
- Lido Key
- Sarasota Office
- Siesta Key
- Osprey
- Casey Key
- Nokomis
- Venice
Our difference
Every owner gets the same three things from us.
We deliver excellent hospitality, creative marketing, and spotless property care to maximize your revenue.
Hospitality focused
Clean, ready-to-enjoy homes and a responsive team earn us top reviews and more bookings at great rates.
Worry less
We offer peace of mind with detailed inspections, smart technology, and a local team. Your investment is safe and well-maintained.
Earn more
Smart marketing and pricing lead to higher occupancy and more revenue.
Siesta Key rental rules
A house and a condo play by different rules here.
A house
On most of the Key, county zoning lets a house in a single-family zone be rented once every 30 days.
A condo
Condos and other homes in multi-family zones can take shorter stays. A condo association can set a longer minimum of its own.
Inside Sarasota city limits
Part of the Key sits inside the city, where a house needs a city certificate of registration before it's advertised.
State license and taxes
Florida's DBPR licenses vacation rentals. Stays of six months or less carry 7% state sales tax plus the county's 6% tourist tax.
Where the place sits matters for income too. The Key has three beaches (Siesta, Crescent, and Turtle), and exact location is one of the things that moves what a rental earns.
Both go into your forecast.
Checked against county, city, and state sources in November 2026.
Siesta Key vacation rental management
A Key rental comes with a long to-do list.
As a Siesta Key property management company, we instantly list your properties on more than 30 sites and use more than 85 booking channels.
We're owner focused, and that makes you more.
- Professional website for your property
- Guest communications and problem resolution
- Guest vetting
- Cleaning between guests
- Light maintenance
- Coordination of skilled maintenance
- 24/7 customer service
- Exceptional guest service
- All required tax registration and rental permits
- HOA coordination with guests (as needed)
- Strict booking agreements
- High rental rates in season
- Typically higher occupancy out of season
- 30+ sites and through 85+ booking channels
- Owner and operators who care
- Professional care for your home
Your listing goes on sites like these.
- Airbnb
- Vrbo
- Booking.com
- Tripadvisor
- Hotels.com
- Marriott Bonvoy
- Hopper
One stay on the Key
Every stay on the Key sets off the same list.
It gets worked through without you flying in.
For owners off the Key
Your Key rental stays in view while you're away.
The owner portal
It's open 24/7 and shows what's happening at your place.
Inspections
Each guest stay ends with a careful inspection.
Locks and monitoring
We use WiFi locks and other monitoring technology on the homes we manage.
Homes we manage
This is how we hand a place to guests.
Each home is cleaned and inspected before the next arrival. Every rental we manage is on our booking site.
See the rentals
Features and benefits
We only make money when you do.
Commission on each rental is how we're paid. Monthly fees aren't part of it, and light maintenance is free. We don't nickel and dime.
Market leading income
- Dynamic pricing adjusts for supply and demand on Siesta Key.
- iTrip properties convert lookers to bookers 5X more often than other rentals.
- See your property on 30+ sites and through 85+ booking channels.
- Extensive digital marketing and behavioral re-targeting increase bookings.
- We get 5 star reviews. Guests willingly pay more for 5-star properties.
Pampered property
- Attentive maintenance and diligent cleaners.
- We keep your home in top shape.
- 24/7 access to what is happening with your home.
- Rental property management is our only business.
- WiFi locks and additional monitoring technology.
- Hotel linens, guest amenities and careful property inspections.
- Guests arrive to a sparkling clean, fully functioning home.
Your property, your rules
- You set the guidelines for occupancy, etc.
- You can control minimum and maximum prices per season.
- Use your Siesta Key, FL property when you want (as long as it's not booked).
- Careful inspections after each guest stay.
Low fees
- You will not only gross more with us, you will net more.
- Competitive rental commission rates.
- Owners are not a source of revenue for us, renters are.
- Free light maintenance.
- No surprises or monthly fees.
How it works
The forecast comes first.
A minute with our simple form shows how we can boost your revenue.
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Fill out our form
Take a quick minute to provide us some basic information about you and your property by clicking the button below. Please make sure your contact information is accurate, including the address of your property.
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Wait for our feedback
If needed, we'll contact you for any additional details and answer your questions. Factors such as amenities, precise location, minimum stay requirements, and decor can influence your earning potential.
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Receive a revenue forecast
You'll receive a revenue forecast that shows exactly how much more you could earn from your property by listing with our property management company, iTrip Sarasota & Venice.
It's honestly that quick and easy!
I'm interestedOwner reviews
Read what our clients have to say about us.
Siesta Key owners said this.
stars based on 1,513 reviews
My wife and I have multiple vacation rental properties on Siesta Key. We have worked with other management companies and iTrip is far and away the best. Not only did they increase our revenue but our places are always in “tip top” shape. They don’t “nickel and dime” us with the small stuff either, which is a relief.
We own a condo on Siesta Key and this company has managed it for almost 7 years. They have exceeded their projections every year and manage so well they make it easy for us.
They are on point and responsive to guests. Take their advice on what your property should need to make guest stays more enjoyable!
Property management questions
Owners on the Key ask us these.
Can you manage my Siesta Key condo?
Yes, and houses too. One owner wrote that we've managed their condo here for almost 7 years.
I own more than one rental. Can you take them all?
Yes. One of the owners quoted on this page has several here.
What will my Siesta Key rental earn?
Nobody can tell you without the address. Send it and we'll work up a revenue forecast. Amenities, exact location, minimum stays, and decor all move the number.
Who cleans between guests?
Our cleaners do, and we inspect after them. The next guest arrives to hotel linens.
How do I know what's going on at my place?
You can watch it through the owner portal at any hour. WiFi locks and monitoring are part of the setup.
Is Siesta Key the only place you manage?
No. We also manage in Sarasota, on Lido Key and Casey Key, and in Osprey, Nokomis, and Venice.
Sarasota and Venice are covered too.
