Cottage holiday rentals in Anna Maria

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Anna Maria

Guests agree: These cottages are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Cottage in Palmetto

4.96 out of 5 average rating, 103 reviews

1930s Cottage + Pool 12 miles to Beach

Located in the heart of historic Palmetto FL, you will find this adorable cottage. This home has 2 bedrooms & 1 bath in the main home with a pull out sofa, as well as, a pool house with a full bath & daybed. You will love the southern charm of this home while relaxing by the pool or having morning coffee on the front porch. There are many restaurants & shops w/in walking distance as well as local parks & preserves. If you love the beach, this home is just a short drive to FL's beautiful beaches.

Top Guest favourite

Cottage in Dunedin

4.97 out of 5 average rating, 333 reviews

Walk Downtown and Waterfront, Designer Getaway

Experience modern coastal luxury in this stylish, spacious upstairs 2-bedroom cottage with designer decor. Steps from Main Street Dunedin. Walk to restaurants, shops, and breweries or take a short stroll to gorgeous sunsets at Dunedin's waterfront. Make the quick drive to beaches such as Honeymoon Island and Clearwater Beach. This pet-friendly getaway boasts 2 king beds, a sleeper sectional, & serene treetop views. Your sunny, coastal escape awaits—book your getaway at the Barefoot Parrot today!

Top Guest favourite

Cottage in Cove

4.85 out of 5 average rating, 126 reviews

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."

Top Guest favourite

Cottage in Indian Rocks Beach

4.99 out of 5 average rating, 186 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes! Welcome to #CocoPalmsIRB, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem that radiates a whimsical, small-town charm, evoking nostalgic memories of carefree childhood summers by the shore. The Gulf of Mexico beckons just two blocks away, offering pristine fluffy sands and unforgettable sunsets. As the sister cottage of Mango, #CocoPalmsIRB invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect getaway awaits!

Top Guest favourite

Cottage in Madeira Beach

4.93 out of 5 average rating, 138 reviews

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.

Guest favourite

Cottage in Pass-a-Grille Beach

4.88 out of 5 average rating, 178 reviews

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.

Top Guest favourite

Cottage in Tampa

4.97 out of 5 average rating, 221 reviews

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake.Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dog 30lb weight limit, no cats, fee $50.

Superhost

Cottage in Bellevue Terrace

4.92 out of 5 average rating, 131 reviews

Private Heated Pool Casita Near Downtown & Beaches

Built in 1925, Our Casaita Verde 2 Bedroom, 1 Bath home still retains its vintage charm but with modern touches. Enjoy watching the 55 inch flat screen TV with HD cable and stay in touch with the world with WI-FI internet. Lounge by the private pool or take in the beautiful evenings on the deck with your favorite beverage. Pet Friendly! Conveniently located near Downtown Sarasota on Bahia Vista with easy drive to Lido Key, our World Famous Siesta Key or I-75 for longer adventures.

Top Guest favourite

Cottage in Bradenton

4.97 out of 5 average rating, 120 reviews

Coastal Style 2BR cottage near Anna Maria Island

Relax with the whole family at this peaceful place to stay. Located in a mobile home/RV park 6.5 miles from Anna Maria Island, which offers some of the most beautiful beaches on the gulf coast. Centrally located between St. Petersburg and Siesta Key. This kid friendly community offers many amenities such as Pickle ball, swimming pool, shuffle board, horseshoes and gym on site. Stay a few days or a few months! Snow birds are welcome! Only 3.3 miles to Sarasota Airport.

Top Guest favourite

Cottage in Bradenton Beach

4.97 out of 5 average rating, 150 reviews

Darling Old Florida Beach Cottage Steps From Gulf!

Fully Renovated Coastal Gem! Welcome to Cottage By The Sea — a beautifully updated retreat just steps from the sugar-white sands and turquoise waters of the Gulf of Mexico on Anna Maria Island. Tucked away in the peaceful community of Bradenton Beach, this charming escape is one of the few remaining “Old Florida” cottages, lovingly restored with modern touches and cheerful, sun-filled décor. Leave your worries behind and unwind in your own slice of island paradise!

Top Guest favourite

Cottage in Bradenton Beach

4.98 out of 5 average rating, 199 reviews

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.

Guest favourite

Cottage in Bradenton Beach

4.88 out of 5 average rating, 285 reviews

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!