Luxury vacation homes inAnna Maria Island, Florida
Our favorites
Discover luxury vacation rentals in Anna Maria Island. All curated by people, not algorithms. Every property is hand-selected, but these are the ones that made us say 'wow'.
Gulf coast tranquility
Experience the laid-back charm of Anna Maria Island, Florida from the comfort of a luxury vacation home. This Gulf Coast barrier island offers pristine beaches, historic fishing villages, excellent restaurants, and Old Florida atmosphere. Whether you're fishing from the pier, exploring Historic Bridge Street, or watching dolphins, premium KEY.co Anna Maria Island vacation rentals provide the perfect island getaway.
Our curated selection of luxury vacation rentals in Anna Maria Island offers something for every traveler - from beachfront cottages with Gulf views to modern properties near local attractions. Each rental home features thoughtful amenities, stylish décor, and the authentic island experience you're seeking. Discover why visitors are enchanted by this unspoiled paradise while enjoying the privacy and comfort of your own vacation home on Anna Maria Island's scenic shores.
Private pool havens
Why KEY
We curate exceptional homes and arrange every detail so you can simply arrive and relax.
Homes that raise the bar
Our portfolio is small on purpose. Every home is professionally managed, design-forward, and vetted for comfort and style.
Services to elevate your stay
After booking your home, complete your stay with tailored services. From pre-arrival groceries and private chefs to in-home massages.
A team who obsesses over every detail
From hand-selecting homes to coordinating logistics, our team makes planning seamless. Your only to-do is to arrive and relax.
Escape beyond Anna Maria Island
Your wanderlust doesn't have to stop here. Discover what other destinations are calling.
Explore Locations
Wherever you're headed, make it memorable with KEY.