Cottage holiday rentals in Anna Maria

Anna Maria Island Tree House

Escape to the AMI Tree House, your elevated island retreat in Bradenton Beach! This peaceful two bedroom, 1 and 1/2 bath, restored home offers a modern coastal feel, a full kitchen, and is perfect for families or small groups. You're just a short walk from private Gulf beaches and the serene Anna Maria Sound. Enjoy the best of island living with all the comforts of home, including free Wi-Fi and on-site parking. Pet Friendly! Automatic discounts applied for stays longer than 7 days and 30 days!

Pass-a-Grille Historic Cottage Unit 2

PASS-A-GRILLE HISTORIC COTTAGE UNIT 2 A fully renovated historic beach cottage located in beautiful Pass a Grille, Florida. Steps from the Gulf of Mexico and Boca Ciega Bay. This is a duplex; Unit 2 - 2 bedroom/1 bath. Household linens, towels, cookware & dishes provided. Appliances include; dishwasher, washer/dryer, flat screen TVs and wi-fi. Vintage-style tiled bathroom and shower. High end window shades on all windows. Front and back patio area w/ BBQ grill. Private parking for 2 vehicles.

Ty's Canal Cottage

"Welcome to Ty's Cottage in Historic Cortez Fishing Village, which is one of Florida's last working fishing villages. Located within walking distance to well known Starfish, Swordfish, Tide Tables Restaurants and Tyler's Homemade ice cream. A short 1.3 mile walk to Anna Maria Island with gorgeous beaches. Short driving distance to beautiful golf courses such as IMG Academy Golf and Manatee County Golf Course. Local fishing charters for outstanding fishing. Outdoor sitting area on canal."

Modern Coastal Hideaway –Patio & Hammock by Beach.

Sandy Toes Cottage is a fully renovated beach home just 2 minutes from Indian Rocks Beach. Enjoy modern furnishings, a bright kitchen, spa-style bath, free Wi-Fi, and a backyard with fire pit and hammock. Walk to local dining and shops—your perfect coastal getaway! **NEW AIRBNB PRICING UPDATE** Starting mid-October 2025, Airbnb will show all-in pricing—including an increase fee of 15.5% Airbnb service fee (charged directly by Airbnb to me the host), cleaning fees, and pet fees if applicable!

Waterfront Retreat•Pool•PingPong•Near AMI Beaches

Relax at this cozy waterfront cottage with a private pool, & a short drive to Anna Maria Island’s white-sand beaches. 2BR/2BA with two living areas include a bright Florida room overlooking the canal. Enjoy ping pong and a putting green ⛳. Start your mornings with coffee on the dock, watching fish jump, or cast a line right from the dock. Fast WiFi, workspace, beach gear, and a kitchen with cooking essentials. Perfect for beach days, family getaways, or a relaxing coastal escape.

Walk to Downtown and Waterfront - Private Yard

Steps to Main Street and minutes to beaches, yet tucked away. Private yard with grill in a prime location. Walk to restaurants, breweries, shops, and live music. Stroll to stunning waterfront sunsets or drive minutes to award-winning beaches such as Honeymoon Island, Caladesi Island & Clearwater Beach. Designer decor. Sleeps 6. Two king bed suites and a luxury couch that sleeps 2 more. Fully loaded for kids, pets and sunny beach days! Treat yourself and book this Dunedin favorite today.

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes IRB! Welcome to Mango, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem radiating a whimsical, small-town charm that evokes nostalgic memories of carefree childhood summers by the shore. Just ✌🏽 blocks away, the Gulf of Mexico beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, Mango invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

Cozy Cottage for Lovers

Relax, reconnect and revitalize in this private, intimate cottage that has everything you need to leave the hustle and bustle behind. Surrounded by lush tropical vegetation in the shade of giant live oaks and located in the Gulfport Arts District, you're a short walk or bike ride from excellent urban parks, restaurants, live music, fashion and art boutiques, dancing at the Gulfport Casino, community theater, and a beautiful beach that looks out over sailboats moored in Boca Ciega Bay.

Historic Holly House on Treasure Island

This charming Beach Cottage is located in the Coney Island area of Treasure Island. This unique set of Key West Style beach cottages are on the beach block only STEPS to the beach! This awesome beach cottage, known as The Historic Holly House, has some unique history. In 1961 the New York Yankees rented out all the cottages in this Coney Island area for spring training. This cottage was the one the Home Run King Roger Maris stayed in before he went on to hit 61 home runs that season.

Ground-Floor Beachfront | Walk-Out to the Sand

Walk straight from your door onto the sand. This rare ground-floor, direct beachfront one-bedroom cottage sits right on the Gulf of Mexico with unobstructed water views and effortless beach access — no stairs, no elevators, no roads. Enjoy your private beachfront patio, a cozy and newly remodeled interior, and your own stretch of sand with lounge chairs just steps away. Perfect for couples or longer stays looking for a relaxed, front-row beach experience in Indian Shores.

Private Heated Pool Casita Near Downtown & Beaches

Built in 1925, Casita Verde blends classic vintage charm with modern comforts. This 2-bedroom, 1-bath home features a 55" flat-screen TV with HD cable and fast Wi-Fi. Relax by the private pool or enjoy peaceful evenings on the deck with your favorite drink. Pet-friendly and conveniently located near Downtown Sarasota on Bahia Vista, with an easy drive to Lido Key, world-famous Siesta Key, and I-75 for day trips and longer adventures. 🌴 Cert# VR24-00152

Bradenton Beach Sunsets 2, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three 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.