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 rentals 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
Blue Lagoon 5
- 2 Bedrooms
- 2 Bathrooms
- Sleeps 6
Dodt House 1, 2 and 3
- 6 Bedrooms
- 4 Bathrooms
- Sleeps 12
Hop Skip and a Beach
- 4 Bedrooms
- 4 Bathrooms
- Sleeps 8
Catchin Rays
- 4 Bedrooms
- 4 Bathrooms
- Sleeps 8
Palms Beach West
- 3 Bedrooms
- 2 Bathrooms
- Sleeps 6
BGs Bungalow
- 4 Bedrooms
- 4 Bathrooms
- Sleeps 8
Casa Sierra 203B
- 2 Bedrooms
- 2 Bathrooms
- Sleeps 6
The Villas 3B
- 2 Bedrooms
- 1 Bathrooms
- Sleeps 6
Coconuts 101
- 1 Bedrooms
- 1 Bathrooms
- Sleeps 4
Forget Me Knot
- 3 Bedrooms
- 3 Bathrooms
- Sleeps 6
Flip Flop Inn
- 3 Bedrooms
- 3 Bathrooms
- Sleeps 6
Blue Water Getaway
- 3 Bedrooms
- 2 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
“We had a wonderful time. The house was perfect location fantastic ! Would recommend!
Stacy S.
“The beds were extremely comfortable, plenty of beach towels, loved having the bathroom out by the pool.
Christina D.
“We would rent this property again. We have been renting on Anna Maria for 20 years and really loved this property and all the furnishings.
Lisa B.
“The house was very clean and furnished with everything you need for a wonderful vacation on AMI. We honestly liked everything with the house.
Tihomir G.
“Great location and cozy home. We rented a golf cart and had a blast cruising around and dining out. We did leave a fishing pole and some tackle in the closet with the bike. Enjoy!
Jason W.
“The place was perfect! The hurricane was a terrible thing but the upgrades and finishes made after that are wonderful. We would absolutely stay here again.
Debbie H.
“It is a wonderful location and great place to stay. Unit is decorated so beautiful with the beach atmosphere and very clean with everything you need to have a great vacation. The pool is wonderful also.
Marcella R.
“This was our 4th time in this house and we were all impressed with the improvements following the hurricane. Booked already for next year.
Sue W.
“We LOVE Catchin Rays!! Beautiful home, decor cozy and feels like home, everything we could possibly need was at our fingertips. Lovely kitchen and dining area, easily seats 8.the bedding / mattresses were high quality and perfect for sleeping. The heated pool / spa was a daily must and was awesome! Location is perfect, walk out the door and 3 minutes to the beach. Perfect location with dining and shopping close. We highly recommend Catchin Rays!
Diane B.
“Great location, close to beach, quiet area and lovely accommodations. Easy key entrance for arrival and our coming and going. Plus felt safe. Many thanks, we will be back!
Marti H.
Quick Links
Contact Us
Stay In Touch
Copyright © 2026 Island Real Estate. All Rights Reserved. Website Design by InterCoastal Net Designs