Anna Maria Island Vacation Rentals

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Make Anna Maria Island your next getaway—choose from 202 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


Condo rentals

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House 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 $446
The Cove at Sandy Pointe #212 3D Tour
2 Bed | 2 Bath | Sleeps 4

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

From $150
Zen Beach Cottage
3 Bed | 2 Bath | Sleeps 6

Zen Beach Cottage - Anna Maria, FL

From $329
Water's Edge 105 South 3D Tour
1 Bed | 1.5 Bath | Sleeps 4

Water's Edge 105 South - Holmes Beach, FL

From $279
Sunrise Garden #5 3D Tour
1 Bed | 1 Bath | Sleeps 2

Sunrise Garden #5 - Anna Maria, FL

From $151

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Recent Anna Maria Island vacation rental reviews

Beautiful home, perfect location! Beautiful bean point beach was a short 5 min walk. Pine Ave was about a 15 min walk. Pool and hot tub were great! We loved hanging out on the dock too. A few minor signs of wear but really well appointed, clean and we thoroughly enjoyed our weekend stay. Our only complaint was wishing there were extra garbage bags but minor issue and we could have purchased more. Of the 7 or 8 rental homes we have experienced, this one is definitely towards the top of the list. We would definitely love to come back.
Lora R. | Jan 2021
all of it
Phillip M. | Jan 2021
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

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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