Anna Maria Island Vacation Rentals

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Make Anna Maria Island your next getaway—choose from 205 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

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Condo rentals

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House rentals

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Duplexes

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Anna Maria Island vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Gulf Breeze 3D Tour
3 Bed | 2.5 Bath | Sleeps 8

Gulf Breeze - Holmes Beach, FL

From $218
The Octagon at Sunbow Bay 3D Tour
3 Bed | 3 Bath | Sleeps 8

The Octagon at Sunbow Bay - Holmes Beach, FL

From $206
Almost Gulf Front 3D Tour
6 Bed | 4.5 Bath | Sleeps 10

Almost Gulf Front - Holmes Beach, FL

From $372
Water's Edge 105 South 3D Tour
1 Bed | 1.5 Bath | Sleeps 4

Water's Edge 105 South - Holmes Beach, FL

From $220
Sunrise Garden #8 3D Tour
2 Bed | 1 Bath | Sleeps 6

Sunrise Garden #8 - Anna Maria, FL

From $119

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Recent Anna Maria Island vacation rental reviews

We loved the screened in porch overlooking the mangrove. We got to watch an osprey there every morning. The place is well furnished and comfortable. Master Bath is a little dated and distance from the beach is a little father, but still not a far walk. We hardly needed our car there!
Scott S. | Jan 2021
The place was as shown on the pictures and even better. It has everything you need for a pool and beach getaway. Great place, clean and well maintained, warm pool, 2 minute walk to the beach. Only a minor issue with the keypad lock, but the vacasa team was there next day to address. Definitively recommended.
Alejandro P. | Jan 2021
The best thing about this little house is it is 5 houses from the beach. It is adorable and functional. The house is clean as long as you don't look at windowsills or vents..deep cleaned it is not. And, if you are a light sleeper be sure and bring earplugs as it is on the main road and you will hear cars and golfcarts whizzing by very early but they do seem to die down around midnight. The backyard was great - we did enjoy dinners out there. Beds were adequate. Kitchen was acceptably stocked - but there was NOTHING left by prior guests so be sure and bring your own salt and pepper even! Dont come expecting luxury and you won't be disappointed.
pam g. | Jan 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!

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