Anna Maria Island Vacation Rentals

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Make Anna Maria Island your next getaway—choose from 187 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 house rentals, condo rentals, duplexes, and more


House rentals

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Condo rentals

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Anna Maria Island vacation rentals for every getaway

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

Almost Gulf Front - Holmes Beach, FL

From $373
Gulf Breeze
3 Bed | 2.5 Bath | Sleeps 8

Gulf Breeze - Holmes Beach, FL

From $235
Zen Beach Cottage
3 Bed | 2 Bath | Sleeps 6

Zen Beach Cottage - Anna Maria, FL

From $197
Seahorse Cottage 3D Tour
3 Bed | 3.5 Bath | Sleeps 6

Seahorse Cottage - Holmes Beach, FL

From $205
Beach Sunset Villa 3D Tour
3 Bed | 3 Bath | Sleeps 8

Beach Sunset Villa - Bradenton Beach, FL

From $142

View 182 more homes

Recent Anna Maria Island vacation rental reviews

We loved the central location and the backyard.
Todd B. | Nov 2020
Location is great. Large heated pool. Short minute walk to beach. House is updated and is very nice. Only negative would be the lighting outside. Pool area has no lighting so swimming at night is hard without area being lit up. Stairs to the house have no lighting and the area below where you park has a motion sensor light that doesn’t kick on until you are already at your car. So just bad lighting all around on the outside of the house. Everything else is great.
Robert G. | Nov 2020
We loved Anna Maria Island and we loved staying in this condo! It was very comfortable and amazing beach access. We were impressed with how clean the condo was and the entire property - pool, tennis courts etc. It was our first visit but definitely not our last!
Greg and Beth K. | Nov 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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