Anna Maria Island Vacation Rentals

Compare 186 vacation rentals. Enter your trip dates to get started.
USA > Florida > Anna Maria Island

Make Anna Maria Island your next getaway—choose from 186 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.

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

housing_type_condo.jpg

Condo rentals

View 65 Condo rentals
housing_type_house.jpg

House rentals

View 65 House rentals
housing_type_duplex.jpg

Duplexes

View 18 Duplexes

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 $361
The Cove at Sandy Pointe #212 3D Tour
2 Bed | 2 Bath | Sleeps 4

The Cove at Sandy Pointe #212 - Holmes Beach, FL

From $121
The Octagon at Sunbow Bay 3D Tour
3 Bed | 3 Bath | Sleeps 8

The Octagon at Sunbow Bay - Holmes Beach, FL

From $217
Beach Sunset Villa 3D Tour
3 Bed | 3 Bath | Sleeps 8

Beach Sunset Villa - Bradenton Beach, FL

From $150
Sunrise Garden #9 3D Tour
1 Bed | 1 Bath | Sleeps 4

Sunrise Garden #9 - Anna Maria, FL

From $157

View 181 more homes

Recent Anna Maria Island vacation rental reviews

Very comfortable home in a great location near the beach. Home was beautifully decorated and had everything needed, except a couple of reading lamps. Never got access to the garage despite repeated calls. Would stay here again.
Terri W. | Feb 2021
Very clean and as the subject says location is great however WIFI is spotty and the Tv was not reliable. No dishwasher but we were only there for 4 days so no problem for us.
Tracey Y. | Feb 2021
Wonderful vacation home! Would stay again. Only improvements would be sprinklers came on at 3 PM at the pool. Dusk or evening would be better. Beach chairs need replacing. Key pickup is unnecessary as there is a lock box. Very confusing emails and text messages as to key/lock box. Overall 5 stars!
Christine B. | Feb 2021

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