BEST 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, staying in an Anna Maria Island Rental is a vacation getaway 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 with amazing Anna Maria Island Rentals. 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 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.
View some of our newest properties
Featured Anna Maria Island Rentals
Palm Isle Village 3211
- 1 Bedrooms
- 1 Bathrooms
- Sleeps 4
Palm Isle Village 3215
- 1 Bedrooms
- 1 Bathrooms
- Sleeps 4
Gulfview Townhomes 4
- 2 Bedrooms
- 2 Bathrooms
- Sleeps 6
Sea Pirate 2
- 2 Bedrooms
- 1 Bathrooms
- Sleeps 4
The Villas 3B
- 2 Bedrooms
- 1 Bathrooms
- Sleeps 6
Our History
ABOUT ISLAND REAL ESTATE
Island Real Estate has been proudly serving Anna Maria Island’s vacation rental and real estate needs since 1970. Over the years, much has changed, but our commitment to providing exceptional service has remained steadfast. The reinvented vacation division of Island Real now offers a wide range of unique Anna Maria Island rentals, from beachfront homes with breathtaking views of the Gulf of Mexico to dog-friendly properties perfect for the whole family. Whether you’re seeking a romantic getaway or a spacious family retreat, we offer properties to suit every need.
For those considering longer stays or permanent moves, Island Real Estate is here to help with over 50 years of experience in Anna Maria City, Holmes Beach, and Bradenton Beach. Our deep local expertise makes us the key to unlocking your perfect home. Explore our selection of homes for sale on Anna Maria Island, or browse all MLS listings to find properties ranging from luxurious oceanfront mansions to charming, affordable condos. There’s something for every taste and budget on Anna Maria Island.
Planning a getaway? You’re just a few clicks away from booking your dream Anna Maria Island rental! Let the Island Real Estate Vacations team help you find the ideal vacation spot. Our local team, with decades of experience living, working, and enjoying the island, is ready to answer any questions about your stay. From the best places to dine to insider tips on local activities, we ensure your vacation is nothing short of perfect. With over 50 years of experience managing vacation rentals and hosting thousands of visitors to Anna Maria Island, we’re ready to make your trip unforgettable.
View Some of Our Beautiful Homes & Beaches
Anna Maria Island Photo Gallery
Recent Client Testimonials
Hear what some of our clients have said about Our Anna Maria Island Rental
“"Thanks for the wonderful stay!!!"
Kimberly K
“"Great job!"
Frank S
“Great front desk staff who are very accommodating to our needs. When guest services were required our issues were dealt with effectively and in a timely and efficient manner.
Julie
“"If you want perfect go to island real"
Anne B
“"A great service as usual, all went smoothly as planned."
Philip S
“"Very Nice house with à very Nice pool area. Very close to the beach."
Joakim, M
“"AMI is a great place for a relaxing vacation!"
Peter K
“"Check out was equally quick & easy! WE loved our stay and our dealing with your company were exemplary. I loved the welcome call after our first night to verify that things were going well!"
Susan H
“This has been our third time renting with Island Real Estate and we have enjoyed every stay. Looking forward to returning soon. We are always happy with the service we receive when staying with Island Real Estate. Thanks again!
Kelly J
“ Service was exceptional!
John
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