Cottage rentals near Anna Maria Island

The Magical Mermaid Cottage

Historic Vintage Cottage ideal for Nature Lovers Step back in time at our 1920s pet-free cottage, nestled in a quiet historic neighborhood near the Riverwalk, Anna Maria Island beaches, and Historic downtown. Renovated in 2019, it blends vintage charm with rustic touches from our family farm in Iowa. Surrounded by native greenery and tucked behind our pink bungalow, it’s a peaceful haven for those who love all that nature offers, history, simple living, good people, and whimsical mermaid vibes.

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."

Flipper's @ Mad Beach Cottage

Flipper's at Mad beach is a few steps away from the sugary sands of Madeira Beach, and close by the famous John's Pass Village & Boardwark where shopping and entertainment is always great. Completely renovated with light porcelain tile, nice furniture, queen bed with memory Thempur-Pedic mattress, exquisite modern shower, tall kitchen cabinets with plenty of storage. Huge private paved fenced backyard with gazebo, great for entertainment and outdoor grilling. You will love the beach decor.

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike

Welcome to your island beach escape! This charming coastal abode boasts all the island vibes you need for a relaxing getaway. Enjoy the quaint historic village (5 houses wide) while being just steps away from the most beautiful beach in Florida! Take a stroll through the picturesque streets of Pass A Grille and soak up the old beach charm. The rental home has hardwood floors, a screened-in porch, and a sun patio, 2 bikes to cruise around the area! open-concept kitchen + bar and smart TVs.

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes! Welcome to #MangoIRB, 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, #MangoIRB invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

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.

Ohana Beachside 2 BR Bungalow - 150 ft from beach

Aloha and welcome to Ohana, our island home where guests are treated like family! This updated 2-bedroom, 1.5-bath retreat offers charm, comfort, and convenience. Enjoy a bright, open living space and a well-equipped kitchen perfect for relaxing or entertaining. Just steps from the beach, with access to a shared 3rd-floor deck—ideal for watching stunning Gulf sunsets. Your perfect Anna Maria Island getaway starts here!

Turtle Cottage - Anna Maria Island

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. Spectacular sunrises are just a short walk away at the Rod and Reel Pier, and the sunsets at Bean Point Beach are second to none, just a few blocks away. This great getaway sleeps up to 4.

New Beach Retreat– Hammock, Patio & Steps to Sand

Sandy Feet Cottage is a beautifully remodeled beach retreat just 2 minutes from the sand in Indian Rocks Beach, Florida. Enjoy an open layout, all-new furniture, a spa-style bathroom, and a private backyard with hammocks, fire pit, and patio seating. Walk to local restaurants, beach bars, and shops. Perfect for families, couples, or friends seeking a stylish, relaxing stay on Florida’s Gulf Coast!