Welcome to Anna Maria Island, FL

Why you should book directly with Casiola vacation homes in Anna Maria Island, FL

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Design your own experience

Customize your vacation the way you want. Enjoy the perks of true comfort and luxury with all of our guest services.

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Early check in
Late check out
Hassle free car hire
pool
Heated swimming pool
Extraordinary housekeeping
Ticket service
Grocery delivery

Guests love their stay in Anna Maria Island, FL

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Airbnb Cleanliness rating

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Rich

“Your home was incredibly inviting, comfortable, and the perfect spot for our family’s Disney trip. We spent two of our days resting at your home and soaking in the amenities (pool, lazy river, slides, happy hour). Your property management company was stellar and was the cherry on top of the experience! I was worried as our plane didn’t land till 11:30 p.m. and had an early morning at Disney the next morning. Your property management company allowed for me to have public deliver groceries prior to our arrival and even put the cold items in the fridge. This allowed for my kiddos to have a nice breakfast before a full day at the parks. Thank you! We will certainly be staying there on our next trip!”

Chris I.

We had a wonderful experience at our Vista Cay condominium. The unit was clean and well stocked. Loved the fact that we were next door to the pool and on the first floor with a lovely view of the lake. Would highly recommend.

Kevin A.

We had an exceptional experiencing renting, now our 4th time, with Casiola rentals in Orlando, Florida! Customer service was extremely responsive to each of our requests, including assistance getting us into the rental property early and sending maintenance out in a timely manner for a minor issue which was promptly rectified. The unit was exactly as described and quite spacious. Amenities were exceptional and location superb!

Gale V.

Amazing villa so spacious. Ideal location only a short easy drive to Disney attractions. Staff helpful us Brits not used to posh plastic box next to front door, to put in rubbish thought it was a seat! Washer and drier were easy to use and very useful. Property clean and good air conditioning. Pool well looked after, clear water a bit cool for the adults, even with great weather over Easter period, the grandkids loved it. We all enjoyed barbeque dinners on the patio.Had to queue to get through security gates pass bar codes did not always work, but could press button so guard at another entrance could let you in.

Things to do in Anna Maria Island, FL

Looking for a fun and exciting activity in the Tampa Bay area? We’ve got you covered with the best local experiences!

What’s going on in Anna Maria Island, FL?

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Staying in a vacation home in  Anna Maria Island, FL

Anna Maria Island, Florida, is a picturesque slice of paradise located just off the coast of Bradenton, known for its charming beach-town atmosphere, stunning turquoise waters, and powder-soft white sand beaches. With its laid-back vibe and friendly locals, Anna Maria Island is the ideal destination for anyone looking to escape the hustle and bustle of everyday life. Spend your days relaxing on beautiful beaches like Bean Point, a tranquil spot perfect for swimming, shelling, and unforgettable sunsets. Explore the island on two wheels by renting a bike and cruising along scenic paths, or hop on the Anna Maria Island Trolley to visit quirky shops, galleries, and cozy cafes scattered throughout the island’s three charming towns—Anna Maria, Holmes Beach, and Bradenton Beach. For an adventure, go paddleboarding, kayaking, or even dolphin-watching along the crystal-clear waters surrounding the island, or cast a line at the historic Rod & Reel Pier and try your luck fishing with breathtaking views of Tampa Bay.

When visiting Anna Maria Island, there’s no better place to stay than Casiola vacation homes, offering unmatched comfort, convenience, and style. Rather than squeezing into a crowded hotel room, you’ll enjoy spacious homes with fully equipped kitchens, luxurious amenities, and inviting living spaces just steps away from the island’s pristine beaches. Whether you’re traveling with family, friends, or planning a romantic getaway, a Casiola home provides the perfect setting to unwind, recharge, and soak in the island’s charming coastal lifestyle. After a sunny day of exploring, shopping, or relaxing on the beach, you’ll love coming home to your private, cozy retreat, making your Anna Maria Island vacation unforgettable.

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