Anna Maria Island Vacation Rentals

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Make Anna Maria Island your next getaway—choose from 199 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
Almost Gulf Front 3D Tour
6 Bed | 4.5 Bath | Sleeps 10

Almost Gulf Front - Holmes Beach, FL

From $349
Mermaid Manor 3D Tour
4 Bed | 4 Bath | Sleeps 8

Mermaid Manor - Anna Maria, FL

From $461
The Octagon at Sunbow Bay 3D Tour
3 Bed | 3 Bath | Sleeps 8

The Octagon at Sunbow Bay - Holmes Beach, FL

From $202
The Cove at Sandy Pointe #212 3D Tour
2 Bed | 2 Bath | Sleeps 4

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

From $115
Beach Sunset Villa 3D Tour
3 Bed | 3 Bath | Sleeps 8

Beach Sunset Villa - Bradenton Beach, FL

From $147

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Recent Anna Maria Island vacation rental reviews

The location of this rental was perfect. We could walk out the door and be at the beach in 2 minutes or the Sandbar in 10. The home was comfortable and perfect for 2 couples and would even accommodate a few children in the 3rd bedroom. Be sure to bring any thing you need to cook with like condiments, salt and pepper and coffee filters. The cupboards and fridge are bare.
Christine H. | Jan 2021
This 2 bed/2 bath was perfect for our family of 4. The extra bedroom fit my teenage daughters perfectly. Having a TV in their bedroom was a plus. The open concept was great for being together and family time. We are from snowy Illinois and we were thrilled to be on Anna Maria for 3 weeks in January! We enjoyed the location of this condo. Close to the beach and right next to a Publix, Walgreens, bike rental, ice cream, sandwich and coffee shops. We rented bikes and enjoyed biking everywhere. We played tennis and pickle ball on the public tennis courts. There is a bike lane and it's easy to get around AMI. Stores, shops and beaches all have bike racks for locking up safely. This is a second story unit and we felt very safe in this location. Our dog came with us and was welcome but not a lot of places to potty him. One small patch of grassy area near parking lot was enough for him though. No dogs allowed on public beaches. I would still rent this unit again as it met all of our families needs. I sure will miss sitting on that porch and having my morning coffee! Beautiful place to watch the sunrise. The view over the mangroves is serene. The bird watching is amazing!
carrie k. | Jan 2021
Close to walking distance for everything you need. Very clean, great view and comfortable. Would definitely return
Marie N. | 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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