Anna Maria Island Vacation Rentals

Compare 188 vacation rentals. Enter your trip dates to get started.
USA > Florida > Anna Maria Island

Make Anna Maria Island your next getaway—choose from 188 great vacation rentals

Ready for an escape to Florida's tropics? Your perfect Anna Maria Island vacation rental awaits! Anna Maria Island is a quaint, 7-mile long gem in the Gulf of Mexico. It’s an island of vibrant contrasts: blue skies, white beaches, fine dining restaurants, and even a few dive bars. Anna Maria Island truly has something for everyone.

Explore Anna Maria Island condo rentals, house rentals, duplexes, and more

housing_type_condo.jpg

Condo rentals

View 63 Condo rentals
housing_type_house.jpg

House rentals

View 60 House rentals
housing_type_duplex.jpg

Duplexes

View 23 Duplexes

Anna Maria Island vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Island Outpost 3D Tour
3 Bed | 2 Bath | Sleeps 8

Island Outpost - Anna Maria, FL

From $353
South Bay Inn 3 3D Tour
1 Bed | 1 Bath | Sleeps 2

South Bay Inn 3 - Anna Maria, FL

From $155
LaRaya Retreat 3D Tour
3 Bed | 2 Bath | Sleeps 8

LaRaya Retreat - Anna Maria, FL

From $295
Anna Maria's Finest 3D Tour
3 Bed | 3 Bath | Sleeps 8

Anna Maria's Finest - Anna Maria, FL

From $306
Coquina Reef 12 3D Tour
1 Bed | 1 Bath | Sleeps 4

Coquina Reef 12 - Bradenton Beach, FL

From $118

View 183 more homes

Recent Anna Maria Island vacation rental reviews

The house was perfect for us. We came to celebrate our 40 year anniversary. The house was clean and we were very comfortable. The pool was amazing. We aren’t technically beach people we just like the beach atmosphere. This was one of our best vacations. Recommend highly. Rick and Angie Taylor
Teresa T. | May 2022
We enjoyed our stay. The backyard was very nice and it was only a short walk to the beach. The house was in good shape and very clean. Owners should replace the carpet in the bedrooms for tile though as it's very worn. The house included enough towels and beach towels and toilet paper. They also had a nice starter pack of soap, detergent, paper towels. We will definitely book again in the future.
Melissa C. | May 2022
From minute one to 3rd day, this beach front cottage was exceptionally equipped, clean, comfortable, convenient and most importantly, just cross one two lane road from front door to beach sand with a remarkable view. The beach, Cortez Beach, was clean and the transparent waters were delicious. What a well kept property. We are eager to book it again.
Antonio H. | May 2022

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning


Find a beautiful Anna Maria Island vacation rental

This charming island draws visitors out to Florida's beautiful beaches and family-friendly activities on the Gulf coast every time of year. Only 60 miles south of Tampa, Anna Maria Island is hidden in plain sight amid the attractions of central Florida.

Where to book a beach house or condo rental on Anna Maria Island

We offer a vast variety of Anna Maria Island vacation rentals, from the town of Anna Maria to Bradenton Beach. The namesake town occupies the northern end of the island, with plenty of local dining, cute cottages, and scenic piers to delight any visitor. Holmes Beach sits a little further south, where you'll find groceries, parks, and the beloved Manatee Public Beach. Drive down the road, and you're in Bradenton Beach—a point of mainland access, and home to some truly cute beach house rentals.

Family activities on Anna Maria Island

Anna Maria Island's picture-perfect beaches are the main attraction for vacation rental guests, so plan to spend plenty of time out in the sand and surf. Explore Leffis Key and test your bird watching skills while taking in the beauty of the wetlands. Skaters of all ages will want to test their chops at the island skate park—just don't forget to wear a helmet! Families looking for a quieter playground should check out Anna Maria Bayfront Park and head to Rod and Reel Pier for lunch afterward.

Beaches near our Anna Maria Island vacation rentals and condos

Of course, we can't blame you for wanting to spend all day at one of Anna Maria Island's gorgeous beaches. Manatee Public Beach is popular for its pristine sands and volleyball nets—an excellent option for a family beach day. Coquina Beach, on the southern end of the island, is also lovely. Check out less-frequented Bradenton Beach vacation rentals for a chance to possibly avoid the crowds.

Come to Anna Maria Island for a taste of the dreamy Florida vacation you've envisioned. You may not be far from the mainland here, but you're worlds away from the stresses of everyday life. Reserve one of our Anna Maria Island vacation rentals and see what it's all about!

Discover Anna Maria Island

The 8 Best Beach Towns Near Tampa for Every Traveler
7 Charming Anna Maria Beach Cottages for a Seaside Retreat
Best Off-the-Grid Vacations for Outdoor Adventurers