Anna Maria Island Vacation Rentals

Compare 194 vacation rentals. Enter your trip dates to get started.
USA > Florida > Anna Maria Island

Make Anna Maria Island your next getaway—choose from 194 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.

Anna Maria Island vacation rentals for every getaway

Dog-friendly Hot tub Internet
Sunset Glow 3D Tour
4 Bed | 3 Bath | Sleeps 8

Sunset Glow - Holmes Beach, FL

From $161
Bay 2 Beach Too! 3D Tour
3 Bed | 2 Bath | Sleeps 8

Bay 2 Beach Too! - Bradenton Beach, FL

From $124
Almost Gulf Front 3D Tour
6 Bed | 4.5 Bath | Sleeps 10

Almost Gulf Front - Holmes Beach, FL

From $299
Key Royale Splendor 3D Tour
4 Bed | 4 Bath | Sleeps 10 (8 Adults Max)

Key Royale Splendor - Holmes Beach, FL

From $184
La Casa Poulos 3D Tour
3 Bed | 3 Bath | Sleeps 6

La Casa Poulos - Holmes Beach, FL

From $240

View 189 more homes

Recent Anna Maria Island vacation rental reviews

Rented out both units A, and B, with a group of friends. Entry instructions were clear, both places were clean, and restrooms were labeled as sanitized. Soap and small shampoo, and conditioner was provided. Pan's, microwave, toaster, propane grill, oven, refrigerator/freezer, cooking equipment, utensils, plateware, dish detergent, new sponges, etc. Were provided on site and propane grill, made full use of all of them! 7 minute walk to all our favorite spots, including the beach(!), and 10 minute drive to Publix. This place is not as high end as some of the other new fancier 2-story places around, but it was affordable, a great location and therefore perfect for us, and we'd definitely stay here again!
Nadia R. | Sep 2020
Location on Anna Maria Island was great!! Beautiful view of the bay from this 2nd floor unit, and only blocks from the gulf side. Very roomy, light, clean and comfortable - such an enjoyable place to hang out, I didnt want to leave! Loved having such a nice kitchen to prepare meals when not eating out. Pool onsite was awesome bonus. Can rent bicycles nearby, choice of restaurants and shops was great (highly recommend the SandBar). So many places to rent in this area, but would definitely return and stay in this unit again. Great value!
William K. | Sep 2020
Such a cool house. I don't want to understate how great the layout is, and how special they've made it with a ton of unique design and functional touches. It looks just like the pictures, and it really feels like a beach escape away from home. But my absolute favorite part was the location. This house is on a private street that is literally a 5 minute walk down a small pathway to what feels like your own private slice of beach (where we saw dolphins diving out of the water very nearby). 100% would seek out this house and especially its location over and over again, for a family vacation. Highly recommended.
J Drew F. | Sep 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!

Discover Anna Maria Island

The 8 Best Beach Towns Near Tampa for Every Traveler
7 Charming Anna Maria Beach Cottages for a Seaside Retreat