Anna Maria Island Vacation Rentals

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Make Anna Maria Island your next getaway—choose from 194 great Anna Maria Island 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.

Anna Maria Island vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Almost Gulf Front 3D Tour
6 Bed | 4.5 Bath | Sleeps 10

Almost Gulf Front - Holmes Beach, FL

From $347
Bay 2 Beach Too! 3D Tour
3 Bed | 2 Bath | Sleeps 8

Bay 2 Beach Too! - Bradenton Beach, FL

From $158
Casa Bonita 3D Tour
4 Bed | 4 Bath | Sleeps 8

Casa Bonita - Anna Maria, FL

From $516
Peaceful Holmes 3D Tour
3 Bed | 3 Bath | Sleeps 6

Peaceful Holmes - Holmes Beach, FL

From $248
East Winds 3D Tour
4 Bed | 3.5 Bath | Sleeps 8

East Winds - Holmes Beach, FL

From $210

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Recent Anna Maria Island vacation rental reviews

The house is so cute and perfect for a family of four!!
Nikki B. | Sep 2020
Living area was perfect, pool area was great and with a short walk to the beach made this vacation one we will not soon forget.
John P. | Sep 2020
This home is close to Bean Point, a short walk from Pine St. where there are many cute shops, restaurants, and dessert options. It is steps away from Rod and Reel pier and the inside of the house is in immaculate condition.
Carlos P. | Sep 2020

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!

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