Anna Maria Charms
Florida
Our top properties
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APRIL Mid Week, SPECIALS! Cortez Boat Resort by AMIsland White Sand Beaches
- 10 guests
- 3 bedrooms
- 3 bathrooms
- Swimming pool
- Free WiFi
- Kitchen
- 4.85 ★
- 4.85 ★
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MAY & JUNE SPECIALS! IMG Lake & Beach Home with Pool White Sand Beaches
- 7 guests
- 3 bedrooms
- 2 bathrooms
- Swimming pool
- Free WiFi
- Kitchen
- 4.90 ★
- 4.90 ★
- 4.90 ★
- 4.90 ★
- 4.90 ★
- 4.90 ★
- 4.90 ★
- 4.90 ★
- 4.90 ★
- 4.90 ★
LAST MINUTE SPECIAL NOW! Beautiful Blue Beach House Kids & Pets OK
- 9 guests
- 4 bedrooms
- 3 bathrooms
- Free WiFi
- Kitchen
- Air conditioning
Escape to Anna Maria Island, a piece of "Old Florida" paradise.
Expect a laid-back, unhurried pace—perfect for unwinding. Our seven-mile barrier island bans high-rises to preserve its intimate, charming character. Days are spent on sugar-sand beaches like Bean Point, paddleboarding the turquoise Gulf waters, or shell-collecting. The island life is all about getting around on golf carts or the free trolley to explore Pine Avenue's boutiques and Bridge Street's historic pier and eateries. Expect stunning Gulf sunsets that are a nightly tradition, fresh local seafood, and the occasional dolphin sighting! Get ready for genuine "Island Time" bliss where the only rush is the tide.
Beyond the beautiful beaches, a few unique attractions capture the spirit of the island. Take a serene trip to the northernmost tip to experience Bean Point Beach, a secluded gem known for its breathtaking panoramic views where the Gulf meets Tampa Bay. For nature lovers, Leffis Key Preserve offers boardwalk trails winding through mangroves, leading to stunning elevated views of Sarasota Bay. Be sure to explore our historic fishing heritage at the Cortez Historic Fishing Village (just across the bridge), the oldest working fishing village in Florida. Finally, you can't miss a stroll down one of the historic piers, like the Anna Maria City Pier or Rod & Reel Pier, for fishing, sight-seeing, and maybe a casual meal over the water.
The culinary scene is focused on freshness and waterfront ambiance. Here are four essential tastes to look for on your trip:
Fresh Grouper Sandwich: A Florida staple! Look for it blackened, grilled, or fried at nearly any seafood spot, like The Sandbar Seafood & Spirits (where you can literally dine with your toes in the sand).
Duffy's Tavern Burger: This cash-only, no-frills local landmark is famous island-wide for serving one of the best and simplest burgers you'll ever have, paired with an ice-cold beer.
The Donut Experiment: A beloved morning stop where you customize your own fresh cake donut with a wide variety of icings and toppings, from maple bacon to key lime.
Key Lime Pie: You are in Florida, so you must have a slice! Try it at one of the upscale waterfront spots, or grab a slice from a local bakery like Hometown Desserts for an authentic island treat.