Recently Viewed 0
Favorites 0

Anna Maria Island Vacation Rentals

Serving Anna Maria Island for more than 50 years

Rich in old-Florida charm and breathtaking views of the Gulf of Mexico, Anna Maria Island is a vacation destination second to none. It’s a place where many go to escape the stress of everyday life and enter a world of pure relaxation. With more than 7 miles of soft, white sand beaches to explore and no high rises or highways to distract the senses, you can really get away from it all on Anna Maria Island. Wake up to the sound of waves crashing in your Anna Maria Island beachfront rental home overlooking the Gulf, and be just steps away from Bradenton beach, Manatee beach, or a short cruise around Bean Point or Coquina Beach. 

At Island Real Estate, we know just how important being able to relax and enjoy your vacation is. Anna Maria Island is Florida’s hidden gem, and we are dedicated to sharing the experiences and relaxation the island has to offer to all of our guests.  Many of our guests only have one opportunity a year to escape the hustle and bustle of everyday life, therefore we go above and beyond to ensure every single one of our guests enjoys their stay with us. We know how stressful planning a vacation can be, especially when traveling from out of state. That is why our booking process is easy and efficient. Our staff is always available to help our guests find the perfect beachfront rental that fits every need they have. Whether you're looking for a pet friendly vacation rental, a Florida beach rental with private pool, or the best beach resort in Florida our staff can find the perfect property for you.

Our guests love our helpful, kind, and customer service-oriented teams that are always available whenever you need them at our Anna Maria Island rentals. Don’t risk losing your relaxing vacation on the best beaches in Florida by booking a vacation rental through a third party. Our vacation rentals do not have any hidden fees or excessive cleaning costs like third-party vacation rental sites do. Additionally, our 5-star cleaning services ensure every property is spotless before our guests arrive. If any of our guests need anything, our teams are located on the island, which means we can fix any issue quickly and efficiently, unlike third-party sites where the property owner may be thousands of miles away.  When you book your next vacation with Island Real Estate you can rest assured that our 50-plus years of real estate and vacation rental experience will proved you with the best vacation experience in Anna Maria City, Holmes Beach, and Bradenton Beach.  

Contrary to popular third-party vacation rental sites, all of our staff are available to help our guests in person at any time of the day or night. Additionally, all of our staff have lived, worked, and played on Anna Maria Island for several decades. Therefore, we know all the best local spots and experiences to enjoy while on vacation, as well as the best restaurants and beaches. We are just a phone call or text away if you need any travel, restaurant, or activity information. We are always more than willing to recommend and assist you in setting up reservations for any activities or experiences you wish to enjoy on your vacation.  

Our main goal at Island Real Estate is to ensure that all of our guests have the perfect vacation. Our 50 years of expertise in vacation rentals have allowed us to manage tens of thousands of visitors to Anna Maria Island. Let our experts do all the planning and hard work, while you enjoy the best Anna Maria Island vacation rental stay of your life while visiting Florida’s hidden gem.  

If you're looking to buy or invest in our piece of paradise - check out our Anna Maria Island Homes for Sale.

anna maria island vacation rental view

The Island

The Island

The Island

More Details
Discover

Things To Do

Things To Do

Things To Do

More Details
View Our

Real Estate

Real Estate

Real Estate

More Details
Design &

Renovations

Renovations

Renovations

More Details
Our History

ABOUT ISLAND REAL ESTATE

Island Real Estate has been serving Anna Maria Island’s vacation rental and real estate needs since 1970. Quite a bit has changed over the last 50 years, but our dedication to our work has remained the same. The recently reinvented vacation division of Island Real offers one-of-a-kind Anna Maria Island rentals, unique vacation experiences, and unmatched customer service. Whether you’re looking for beachfront rentals overlooking the Gulf of Mexico, or pet-friendly rentals big enough for the whole family, you’ll find the perfect Anna Maria Island rental here. For those looking to make their stay on Anna Maria Island more long-term or permanent, Island Real Estate is here to help. With more than 50 years of real estate experience in Anna Maria City, Holmes Beach, and Bradenton Beach, Island Real is your key to Anna Maria Island. Check out our homes for sale on Anna Maria Island, or browse all MLS listings on the island! From stunning oceanfront mansions to affordable condos, there’s something for every taste and budget here on Anna Maria Island.

You're just a few clicks away from booking a relaxing ANNA MARIA ISLAND RENTAL for your next vacation! Let our Island Real Estate Vacations team help you find your perfect getaway. Our local team has worked, lived, or played on the island for several decades and can help with any questions about the Island including where to stay, where to eat, and anything else to help make your vacation perfect in every way! Island Real Estate has managed tens of thousands of visitors to Anna Maria Island, so let our expertise work for you.

Recent Client Testimonials

Hear what some of our clients have said about us