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FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay

Experience life 4 blocks from the Gulf, ½ mile to Siesta Key — America’s #1 Beach. With effortless access to Sarasota’s dining & arts scene, Siesta’s white sand beaches, St. Armand’s, & Gulf Coast adventure! 2BR boutique bungalow • Sleeps 6 • 4 beds Situated in the coveted Coastal District (‘West of Trail’) — chef kitchen, beach gear, Smart TVs, marble spa bath, laundry, fast Wi-Fi. Grill lobster under stars, unwind in your tropical garden, & walk palm lanes to cafes, and waterfront sunsets.

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

Welcome to the Paradise Fun House, the ultimate spot for your dream bash! Our Airbnb oasis is packed with tons of fun and activities for an epic stay. Cruise around on free bikes or kayaks, fish with top-notch gear, challenge friends to mini-golf, chill in the hot tub, or enjoy our game collection. Golf clubs and beach gear are ready to roll. Our spacious layout is perfect for partying all night long. Book now for the ultimate fun or relaxing experience! Boat/Dog-sitting/cleaning are available

Beach Escape & Pool, steps to Beach & restaurants

One block from beautiful beach & waterfront dining. Newly renovated Villa in quaint quiet condo building close to everything on Anna Maria Island. Pickleball across the street. Pool literally out your back door. Perfect for a small family or a romantic getaway. *Min. renter age 25. Two minute walk to beach, trendy Bridge Street shops, marina, restaurants, bars, boat tours, mini golf and more. Brand new beds, furniture & appliances. Kitchen has everything you need. Beach supplies in hall closet.

AMI Dock of the Bay - "On the Water" 1st Floor

AMI Beach + Bay Home with Fishing Pier + Heated Pool on Sarasota Bay - "Dock of the Bay" / Entire 1st floor of Duplex called "On the Water" • Unbelievable views of water + birds + wildlife + night lights! • Relax with fish jumping and birds flying along 1 of only 34 coveted docks/piers south of Cortez Bridge! • Fish off dock and rod holders! • Heated pool w/ spa jets/benches only 10 ft from Bay! • Walk 2 blocks to Bridge Street/Key West-style restaurants, bars. • Live Music heard on dock!

Carissa A | Beachside Duplex | Golf Cart | Pool

Welcome to Carissa Loft A, your completely private half of a beachside duplex on AMI! The duplex is designed back-to-back, meaning you have your own private indoor and outdoor spaces, entrance & pool-No shared amenities! Loft A includes: 3 beds, 2 baths, full kitchen, 2 separate living areas, balcony, heated/cooled cocktail pool, & garage w/golf cart! Ideal for up to 6 guests. Need more space? You can book both sides of the duplex for larger groups while still enjoying separate living areas.

Bradenton Beach Sunsets 3, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with a queen pull out couch make this a great location for, solo guest, business travelers, and families. . Beach chairs/umbrellas/etc. provided. 3 blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

Anna Maria retreat house

Elevated home with all the amenities. Walking distance to the beach, chairs and towels provided. Relax in the backyard patio, including pool with waterfall . The shaded balcony overlooks the pool if you need to escape the sunshine. There’s a free trolley that runs all day in AMI if you don’t want to take the car out. The house is located across the street from Bimini Bay, enjoy a jog through these side streets in the morning. Local shops and restaurants that will not disappoint .

New! Resort-Style Pool + Hot Tub + Beaches + IMG!

🌴 Welcome to Palm Days – Your Private Luxury home Near IMG & Anna Maria Island 🌊 🏝️Escape to a fully renovated tropical retreat where every day feels like vacation! This stunning home combines modern luxury with a resort-style backyard designed for pure relaxation and fun. 💦 Enjoy the expansive Heated Pool and Hot Tub ☀️Sunny oversized sun shelf - perfect for relaxing or for the little ones to play! ⚽️ 3.4 miles IMG Sports Academy 🏖️ 5 miles Anna Maria Island Beaches

The Riverview Nook in Downtown!

Stylish 2 bed, 2.5 bath cottage, walking distance to the beautiful Manatee river and historic downtown Bradenton. Only a 20 minute drive to Anna Maria Island and neighbors major cities, Tampa and Sarasota. A cozy house, with stunning professional interior design. Clean-ability was highly prioritized with this home, with virtually every surface, from the couch covers to the duvet inserts being washable, or bleach-able. Be advised the third bed is a pullout bed in the living room!

KING Bed + Anna Maria Island Beaches + Beach Gear!

⚓️🦩Welcome to the Coastal Flamingo! Your nautical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this coastal escape!

Casa Bella-5BR/Waterfront/Pool/Spa-9 Min AMI

Beautifully renovated 5 bedroom home. Located 3 minutes from beach access and 9 minutes to Anna Maria Island. A massive waterfront patio with string lights and heated pool and spa encompass this house. Master bedroom with walk-out to spa. Custom double walk-in shower in master suite. Family room with 86" television, decorative fireplace, and 15' ceiling. Roku TV’s in every bedroom. Outdoor propane grill. Beach chairs, umbrella, and cart. We welcome you to Casa Bella.

Relaxing 3BR Retreat+ Hot Tub + Pool +Beaches +IMG

🌴Welcome to Beachway Haven! This 5-Star ⭐️ hideaway is just mins from Anna Maria Island's Pristine Beaches & the Gulf of Mexico. Dive into relaxation with your own Heated Saltwater Pool & Spa Hot Tub, nestled in a tropical oasis. Only a skip away from Golf Courses, Nature Parks, IMG Academy, & Palma Sola Causeway's Beach Access – your gateway to Horseback Riding, Kayaking, & endless sandy adventures. Shopping & dining are only a few mins away too!