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.

Michalah Casciani

I am originally from Connecticut but am a firm believer of following the wherever life takes you. I have spent the past five years living in California surfing and kayaking amongst great white sharks, as well as hiking in the redwoods. Being outdoors and near or on water is what keeps me grounded. I have had the pleasure of supporting customers in a wide variety of spaces from Silicon Valley to Emergency Departments and thrive when I am working as part of a team to ensure an excellent customer experience. Over the past 10 years I have visited Anna Maria Island a several times to see my older sister and her family. Last March I came to visit and realized it was time to move when getting on the plane felt like I was leaving home, not going home. I plan on being here for a long time and am excited that this company is part of my new adventure!

Angela Pavan

Hi, I’m Angela! I am originally from New Jersey and have lived in Florida for almost a decade. In my spare time I love going on adventures with my 4 fur babies. I’m currently attending university for my BA in Graphic Arts. Since starting with Anna Maria Life Vacations in February 2022 I have been able to bring my skill set of graphic design to light with a lot of the graphics and ads you’ll see from us! My main role is booking your vacation in paradise!

Alyah McCrea

Hey, I’m Alyah McCrea! I’m a local gal born and raised in Bradenton. I spend most of my free time with my wonderful husband Wyatt adventuring and enjoying all there is to see in Florida! I started with Anna Maria Life Vacations in February of 2022. I enjoy my role in making people’s vacation dreams come true! Can’t wait to welcome you to paradise!

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!

Emily Klodnicki

Emily is a true Florida Native who loves everything the beach has to offer, including the sand! She spends her free time playing with her two little boys, husband, and many pets. Her favorite pastime though is photography. She can literally spend all day at the beach with her loved ones taking pictures, swimming, sunbathing, and gathering shells. When she is not at the beach, you can find her at Anna Maria Life Vacation Rentals working happily alongside her coworkers and friends. She is truly blessed to call Anna Maria her home and wouldn’t have it any other way.

Val Crisp

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.

Tyler Popham

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!

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.

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