Billi Gartman

Billi fell in love with Anna Maria Island during a visit for her best friend's wedding. She left just long enough to pack up her big city life and make the move to this small island town! She knew in her gut this was the place to grow roots. Since that time, she has built a career, a life, and a family here on Anna Maria Island. Over the past 10 years she has been honored to work with so many wonderful people, and build thriving businesses on the island through networking and personalized face-to-face relationship building. The island is her home and she has a constant finger on the pulse of the community, vacation rentals and the local market

Matt Lyndon

Amy Smith

I moved to Florida in 1999 from Long Beach Island, NJ where I grew up. I had come here on vacation and loved it so much I drove home, packed my bags and I have been here ever since. My daughter, who is 20 and awesome, has lived on the island for many years. Like so many others, I love the beach and catching as many sunrises and sunsets I can. After working with the same vacation rental company for 12 years on the island, it was time for a change. I only sent my resume out to one opportunity I saw online and fortunately it was with Coastal Cottages, which is now Anna Maria Life Vacation Rentals. Billi and I hit it off right away and we dug in and went to work. It’s been exciting to watch our hard work transpire into something so great.

Cheryl Shih

Hello! It's me, Cheryl Shih. I am originally from Rochester, NY, but have called Florida home since 1996. I have a 17 year old son, Erik, and a sweet pup named Hank, my pit mix, who rescued me in March 2019. He's the first dog of my life and we are deeply in love. I have worked in the hospitality industry for nearly 30 years and love working with our guests to plan the perfect vacation. A few of my favorite things are; yoga, reading a good book, spending time with family and friends, and floating in the sea while working on AMI. I also love to ride my bike, Angel, and explore the island. Everyone should rent a bike while on the island, it's an amazing way to get around and see everything. My goals; finish the book I started writing in 2016, get into full pigeon pose during yoga, see a dolphin, and make vacay dreams come true!

Dana Fasciglione

After 25 years of living in New York, I decided it was time to switch things up a bit! With many relatives living on Anna Maria, I've vacationed here since childhood. After my most recent visit, I packed my car and headed South. I have worked various jobs, but never quite knew where my career path would lead me. I am so grateful for the stepping-stones that led me to Anna Maria Life, and my wonderful group of colleagues. With the combination of my experience in customer service and my Bachelors in Psychology & Communications, guest services is where I belong!

Brian Shoemaker

I am Brian Shoemaker. Originally from Kentucky. My wife & I would vacation in Florida once or twice a year. We decided to move to Florida 7 years ago so she could be closer to her family. My mom & sister are still in KY, but we hope to get them moved down here, too. I worked a few jobs before finding my place with vacation rentals. Once I started working on Anna Maria Island, I knew this is where I belong. I was fortunate to be brought on with this amazing team at Anna Maria Life Vacation Rentals, formerly known as Coastal Cottages. Working on an island & along with a dedicated team has truly been a blessing. When not at work, I'll be on the golf course with my dad. We were able to convince him & his wife to move down from IL a year ago. Getting out on the course with him like I used to growing up is so much better because we can practically play all year long. IF I'm not on the course, I'll be home taking care of our fur babies. 3 dogs & a cat. They are a handful.

Tommy Winkler

Tommy is originally from Indianapolis, and has lived in Florida for eight years. He’s spent 20 years in construction, maintenance, and damage restoration. His vast knowledge and wide ranging skill set allow him to perform tasks well above and beyond those of the average home maintenance professional. Tommy has been with the company since the beginning. He knows this island and our homes inside and out and is a huge asset to Anna Maria Life Vacation Rentals. Tommy and his wife Dorothy have three boys, He loves country music, Colts football, and family time.

Kelsey Moore

Jena Greco

I relocated to Bradenton Florida in 1989 from the Northwest suburbs of the Chicago area with my parents and my older brother. I attended elementary school, middle and high school here. In 2010, I was blessed with my beautiful daughter who is now 13 years old. I love to go fishing whenever I get the chance but most of all, I love spending time with my daughter and my family going out on the boat any chance I get. I have 15+years in the customer service and the property management fields. I am very passionate about providing a seamless property management experience and I am very consistent and committed with all my customers.

Lindsey Lewis

Lindsey Lewis is the Head of Marketing, content creator, and resident computer nerd at Anna Maria Life Vacation Rentals. Among other things, she manages our email marketing campaigns, social media, and most of our website content and upkeep. Lindsey thrives in dancing the line between technical and creative, and loves that her position offers her the opportunity to do just that. Lindsey worked in resort operations and taught customer service for a large vacation company for several years before leaving corporate America to concentrate on marketing full time. Lindsey left her beloved Anna Maria Island in 2017, to raise her two boys closer to extended family. She lives in Indiana but continues to work on the Island remotely. She comes ‘home’ to the Island several times per year to work from the Anna Maria Life office, reconnect with coworkers and friends, and float in the Gulf of Mexico. Lindsey considers herself the evangelist of the virtues of the meandering solo road trip. She loves traveling, outdoor adventures, creative writing, music, and the oxford comma.

Amber Miller

My name is Amber Miller, and I am the Bookkeeper for Anna Maria Life. I am an accomplished college graduate that holds a Bachelor of Science degree. Although numbers are my best friend, I have had the opportunity to explore a multitude of different opportunities, including working with financials at a bank, taking on the role of a tour guide for a brewery, teaching preschool and owning a general contracting construction company. After graduating in 2013 from Drury University in Missouri and vacationing often to the Bradenton/Sarasota area, I decided in 2015 to pack what I could in my car and leave my hometown and all I ever knew. What a great decision that was, as I’m still in this beautiful paradise today. I enjoy any outdoor activity, music and attending concerts, educational adventures, fishing and taunting my Chihuahua, Hot-Rod. My favorite part of being a bookkeeper is being able to work with homeowners and our team to define the details. – Everyone loves the “bean counter”.

Sarah O'Leske

Hello! My name is Sarah O'Leske. I was born and raised in North Dakota and knew very early on that I was meant to live in warmer weather. In college, I moved "south" to Colorado where I spent 17 years in the Fort Collins/Loveland area. My family and I finally decided it was time to find a true warm climate, so we visited Anna Maria Island...as a starting point. We spent only a few days here and knew this was home. Three months later, in 2015, we bought a house here and made this paradise our forever place! I look forward to many more years on Anna Maria Island, and I am excited to help others visit paradise through Anna Maria Life Vacation Rentals!

Colette Fernandez

Born and raised in the sunshine state, Living the dream in paradise every day! I enjoy showing around this beautiful small island I call home, creating new memories with people from all over the world.

Daisy Bueno

Hey There! My name is Daisy Bueno and I am a beach enthusiast who is all about planning the perfect vacation. I am originally from Medellin Colombia, but I call Anna Maria Island my home. Since High school, I've been diving into the world of vacation rentals helping people experience their dream getaways here on AMI. It is such a cool opportunity to welcome people from all over the world to where I grew up . When I'm not busy making vacation dreams come true, you'll find me at home whipping it up in the kitchen, traveling, or at a concert.

Rachael Denzin

My name is Rachael Denzin. I was born in raised in Florida, living across the Skyway Bridge over in St. Pete during my childhood/teen years. I discovered Anna Maria Island and was enamored with its' charm, so I never left! I was lucky enough to land a role in the Vacation Rental space and it changed my life. I met my husband and my very best friends here, and I get to wake up and work in paradise each and every day. I am fortunate to work alongside some of the very best people I know here at Anna Maria Life, getting to share our love of the island to people from all across the world. When I'm not working, you can catch me belting Taylor Swift or musical theatre jams, thrifting, or spoiling the #official Goodest Good Boy in the World, my 80lb lap dog, Cody.

Tommy Kilpatrick

My name is Tommy Kilpatrick but most people call me “Tiki”. I was born and raised in northern Michigan. In 2014 I moved to Anna Maria Island with only my tools and clothes and whatever else I could fit in my jeep. And after a year of living I met a beautiful woman who I would end up marrying. We got married in Las Vegas and yes Elvis walked her down the aisle and we now live in the Cortez fishing village just off the island. Most of my life I worked in almost every aspects of construction and when I arrived here in Florida I started working as a repair man/ maintenance man. And I guess you can say the rest is history…

Alex Wheeler

JP Beaubien

J.P. grew up on Anna Maria Island. He loves spending time with his wife and two boys. He also loves to play music, cook, and travel. “What I really love about my job is not only do I get to work on an island paradise, but I get to work with some of the greatest people that I know!"

Alyssa McKinnon