Featured Properties

Anna Maria Island isn’t a place where you go to the beach. When you are on Anna Maria Island you are at the beach.

Imagine lying on a pristine stretch of powder white sand, shaded by swaying palms from the balmy Florida sunshine. A pod of dolphins plays in the sparkling water nearby. There are no high rises or large resorts, just Old Florida charm and a laid back vibe.

This daydream becomes reality on Anna Maria Island, a slice of paradise beloved by snowbirds looking for a winter getaway and beach bunnies in the summer. Named American’s #1 Beach Vacation Destination by TripAdvisor in 2014, it’s not difficult to see why this island beach is on so many traveler’s bucket lists. A real estate agent and traveler’s dream alike, the island is home to hundreds of vacation properties, with some of the most popular condo rentals and house rentals located right along the popular gulf beaches.

At Anna Maria Island Rentals, we offer a wide range of professionally managed, modern vacation rentals that allow you to experience this wonderful island at your own pace. With beach condos and beach cottages just steps from the ocean, guests enjoy amenities such as private pools, wifi, gulf views, and more. Check-in is made simple with our property management system, so guests have peace of mind from start to finish.

Families and couples alike will appreciate the endless beautiful beaches, such as Bradenton beach and Holmes beach, that stretch the length of the seven mile barrier island. Take a gulf drive up historic Pine Avenue to see some of the most luxurious bayfront rental properties the area has to offer. Exploring the island is easy with a free trolley service and rental shops for bicycles and golf carts, or take a stroll on the beach at your leisure.

Discover specialty boutiques and local art galleries in the north end of the city of Anna Maria before sampling fresh-caught local seafood at one of the beachfront restaurants. While Anna Maria beach is the most well-known on the island, head to Manatee public beach for a more family-friendly vibe, or explore one of the hidden golden sand beaches along the gulf coast shore.

In the evening, watch the fiery sunset light up the Gulf of Mexico from local favorite Coquina Beach while you share a bottle of bubbly with your loved ones. Return to your beach house at the end of a long day and relax in your private cabana or heated pool under the stars. With Anna Maria Island Vacation Rentals, your dream vacation home is waiting for you at the end of the day.

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Sandy – Hamilton

Couple kissing on the beach at sunset.

We booked this condo last minute and are so glad we did! Our vacation was everything we had hoped for and more. My husband and I are avid walkers and we enjoyed walking miles along the beach every day. There are many excellent restaurants within walking distance of the condo which was especially nice not having to drive. Free trolley that takes you anywhere on the island, wow!

Sandy - Hamilton

Brittany – Toronto

Woman in leather jacket and hoodie.

This was the best vacation we have ever had. This condo is absolutely beautiful. Everything is new, and very clean. Wonderful view of the Gulf. We had a amazing experience and will recommend this condo to all of our friends and family!

Brittany - Toronto

Anna Maria

Couple sitting on a pier and embracing.

First of all I have to say, Terry is just awesome to work with. The return calls, the follow up is second to none. I live in Florida and have stayed just about everywhere in the state. Anna Maria is wonderful! After every place I’ve been in the state, AMI is tops. Siesta key is a close second. The condo is perfect, everything you need to accommodate all your needs. The pool is great, beach is pristine. If you’re looking for the perfect vacation…make sure you look up Terry White!

Zero Complaints

Parents and child standing in beach surf.

We stayed at this condo for 10 perfect days. The condo was great, clean with great appliances, comfortable king sized master suite etc. One minute to an amazing beach! The condo pool was perfect in the evenings. The free Trolley is right outside to take you to a great grocery store next to any “spirits” you need. Lots of restaurants. The sunsets over the gulf is almost indescribable it’s so wonderful. Zero complaints, it’s heaven…..go for it

Perfect Getaway!

This condo was perfect for your family of 4. Terry was a great help before and during the trip. We had a wonderful time! Thanks Terry!

Submitted: Nov 3, 2017 | Stayed: October 2017

Maggie Joos

Stephan Hoeft

The condo is awesome. There is a nice pool and the gulf is only a minute to walk. Around the condo you find many fantastic restaurants. We had a great vacation there!

Stephan Hoeft