Your Anna Maria Island Property Deserves a Manager Who Actually Lives Here

Since 2016, we've combined 85+ international booking channels with a local team that knows every neighborhood on the island, from local code enforcement to seasonal tide patterns. The result: more revenue, less stress, and a property that's cared for like it's our own.

Maximize Your Rental Income While We Protect Your Home

Receive a Comprehensive Proposal

Current Rental Status

Currently renting on my own

Currently using a property manager and exploring

Currently not renting but looking at options

Professional vacation rental management designed to protect your home, grow your income,

and give you real peace of mind.

Hundreds of properties managed with transparent reporting

Trusted by homeowners and real estate professionals

Focused on long-term income, care, and property value

Professional vacation rental management designed to protect your home, grow your income,

and give you real peace of mind.

Hundreds of properties managed with transparent reporting

Trusted by homeowners and real estate professionals

Focused on long-term income, care, and property value

Your Second Home is Our First Priority

iTrip is a full-service property management company focused on helping homeowners turn their properties into high-performing rentals, without the stress of having to manage it themselves.

Our local team treats your home like it’s our own, focusing on what matters most:

Strong, consistent rental income
Proactive care and maintenance
Exceptional guest experiences that protect your property

You’ll always know what’s happening with your property. We believe in clear communication, honest guidance, and long-term relationships built on trust.

Real people. Local expertise. Powerful technology.

Here's What Sets iTrip Apart

Exceptional local home care and powerful technology work together, to protect your home, grow your income, and give you peace of mind.

Exceptional Home Care

Your home is proactively cared for through detailed inspections and ongoing oversight. This level of care protects its condition, preserves long-term value, and support consistently strong guest experiences.

White-Glove Housekeeping

Five-star cleaning standards ensure every stay begins spotless and well-prepared. This leads to better reviews, repeat bookings, and pride of ownership.

Advanced Marketing & Distribution

iTrip’s innovative technology and marketing systems give our listings priority placement across top booking channels. Increased visibility means stronger demand, more bookings, and higher revenue for our owners.

24/7 Guest Support

Guests have access to local support around the clock for questions or issues. This helps prevent small problems from becoming big ones.

Dynamic Pricing Strategy

Rates are continuously optimized based on demand, seasonality, and local trends to maximize revenue without sacrificing occupancy.

Local Ownership with National Backing

Your property is locally owned and managed with the support of a proven national vacation rental network built over more than 20 years.

When your municipality has questions about your rental, we’re the local point of contact.

“To my surprise and financial enjoyment, my property grossed over $200,000 in one year. The level of professionalism and financial reporting was second to none.”

– Anna Maria Island Homeowner

Here's What Sets iTrip Apart

Exceptional local home care and powerful technology work together, to protect your home, grow your income, and give you peace of mind.

Exceptional Home Care

White-Glove Housekeeping

Five-star cleaning standards ensure every stay begins spotless and well-prepared. This leads to better reviews, repeat bookings, and pride of ownership.

Advanced Marketing & Distribution

24/7 Guest Support

Guests have access to local support around the clock for questions or issues. This helps prevent small problems from becoming big ones.

Dynamic Pricing Strategy

Rates are continuously optimized based on demand, seasonality, and local trends to maximize revenue without sacrificing occupancy.

Local Ownership with National Backing

Your property is locally owned and managed with the support of a proven national vacation rental network built over more than 20 years. You get personal attention paired with the strength and reach of a trusted brand.

Your Second Home is Our First Priority

iTrip is a full-service property management company focused on helping homeowners turn their properties into high-performing rentals, without the stress of having to manage it themselves.

Our local team treats your home like it’s our own, focusing on what matters most:

Strong, consistent rental income
Proactive care and maintenance
Exceptional guest experiences that protect your property

You’ll always know what’s happening with your property. We believe in clear communication, honest guidance, and long-term relationships built on trust.

Real people. Local expertise. Powerful technology.

About Us

Todd Wahl brings 30+ years of property management experience to every decision we make for your property. His background spans multi-family residential management, technology solutions, and operations leadership, including roles as President at Resident Interface and VP of Sales & Operations at Pierce Hamilton & Stern. He holds a BS in Finance from Penn State. His focus: maximizing efficiency and driving revenue growth for every property in our portfolio.

Nicole Wahl brings customer care and client relations expertise honed in real estate title services. Her focus: making sure every guest gets personalized service, and every owner gets less stress.

Together, Todd and Nicole launched iTrip Anna Maria Island in 2016 and also operate iTrip Bradenton-Sarasota, giving them deep coverage across Manatee and Sarasota counties. Whether your property is a beachfront bungalow on Anna Maria, a condo in Holmes Beach, a villa on Longboat Key, or a home in Lakewood Ranch, we have the local knowledge and vendor relationships to deliver five-star service.

About Us

Founded in 2008 by short-term rental owners, iTrip® was created to provide a higher level of service for both property owners and guests. Today, iTrip has grown to over 100 locally owned franchise locations managing 4,000+ properties across North America.

Our dedicated local property managers deliver boutique-style, hands-on support while leveraging powerful marketing across major booking platforms and 80+ listing websites. This approach helps owners maximize revenue through direct bookings and partner sites, while guests enjoy a consistent, professional, and worry-free experience every time they stay with an iTrip property.