We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Cottage rentals near Anna Maria Island

Find and book unique cottages on Airbnb

Top-rated cottage rentals near Anna Maria Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

A fenced-in outdoor area features a swimming pool surrounded by a red brick patio. Sun loungers are positioned beside the pool, and a pool house is visible in the background, complemented by lush greenery and large trees draped with moss.

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.

A cozy living area features a colorful mermaid-themed couch against a backdrop of textured wooden wall planks. A mounted television sits above a decorative fireplace. Soft lighting from a ceiling fan enhances the open and welcoming atmosphere, accompanied by natural light from the front door and nearby window.

Cottage in Bradenton

4.87 out of 5 average rating, 100 reviews

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.

Top guest favorite

A cozy living area is displayed, featuring a patterned sofa and a wooden coffee table with a small plant. A large television sits on a white dresser, while an air conditioning unit is installed above. The entrance door is visible, along with a wall clock and decorative wall art.

Cottage in Cortez

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 favorite

A round dining table with a dark wood finish is accompanied by four white wooden chairs. The chairs feature a classic design, and the arrangement is set on a light marble floor, with kitchen cabinetry visible in the background.

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.

The cottage features a welcoming exterior with a screened-in lanai, framed by decorative beams and charming window boxes. Lush greenery surrounds the property, and a large tree adds to the tranquil setting. A pathway leads to the front door, enhancing the inviting atmosphere.

Cottage in Sarasota

4.8 out of 5 average rating, 265 reviews

Cozy Cottage by the Bay

Charming and historic decorator cottage near Downtown Sarasota. Located in the highly desirable, quiet, and safe neighborhood of Indian Beach - Sapphire Shores. Just a short drive to some of the nations top rated beaches like Siesta Key Beach. One of the best features of the home is the enclosed lanai at the front of the house. Perfect for enjoying Florida's coveted indoor/outdoor living. It has a private fenced in backyard, with a fire pit. Off street parking for 2 cars in the driveway.

A wooden boardwalk leads directly to the beach, framed by sandy dunes and swaying grass. The clear blue sky meets the calm waters of the Gulf, creating an inviting scene for beachgoers. The soft beach sand stretches out, blending seamlessly into the horizon.

Cottage in Saint Pete 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 favorite

An inviting heated saltwater pool is softly lit in the evening, surrounded by sun loungers. The vibrant mural features a large tropical flower. A close-up shows a decorative pillow with the word 'SUNSET.' The living area offers a cozy seating arrangement with colorful cushions and a decorative coffee table.

Cottage in Indian Rocks Beach

4.96 out of 5 average rating, 158 reviews

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!

Top guest favorite

A vibrant blue exterior is complemented by white shutters and railings. Tall palm trees sway in the background under a clear blue sky. A shaded wooden seating area invites relaxation, with the entrance visible through glass doors leading into the cottage.

Cottage in Bradenton Beach

4.97 out of 5 average rating, 207 reviews

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.

A private pool is surrounded by a paved area, featuring two lounge chairs positioned near the water. Green foliage adds a natural touch, while a white fence encloses the space, creating a secluded atmosphere. The clear blue water reflects the sky, inviting relaxation.

Cottage in Sarasota

4.92 out of 5 average rating, 132 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.

Cottage in Bradenton Beach

4.88 out of 5 average rating, 286 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!

A private outdoor space featuring a heated pool and spa, surrounded by palm trees and lounge chairs. The vibrant blue cottage is visible in the background, complemented by carefully arranged landscaping. A pathway of stepping stones leads toward the entrance of the cottage.

Cottage in Anna Maria

4.96 out of 5 average rating, 250 reviews

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.

Top guest favorite

An open-concept kitchen and dining area features modern fixtures and wooden accents. A large island bar is surrounded by high-backed chairs, with a dining table visible in the background. Light blue walls and stylish light fixtures create a bright atmosphere.

Cottage in Indian Rocks Beach

4.98 out of 5 average rating, 158 reviews

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!

Popular amenities for cottage rentals near Anna Maria Island

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Top guest favorite

Cottage in Safety Harbor

4.96 out of 5 average rating, 192 reviews

Harbor Oasis | Hot Tub | Private | Lush Backyard

Top guest favorite

The outdoor pool area features a clear water pool surrounded by lounge chairs and vibrant umbrellas. A bright blue building is visible in the background, complemented by colorful accents along the poolside. Lush greenery adds to the relaxed atmosphere.

Cottage in Dunedin

4.91 out of 5 average rating, 125 reviews

Sunny - Key West Vibe Cottage - Pool - Walkable

Top guest favorite

A coastal-style duplex is framed by lush tropical landscaping, featuring palm trees and colorful flowering plants. The exterior showcases light-hued siding, a spacious front porch with railings, and two garage spaces below. A clear blue sky enhances the inviting atmosphere of the property.

Cottage in Holmes Beach

4.94 out of 5 average rating, 64 reviews

Close to the Beach+ Private heated pool and spa!

A charming coastal cottage is depicted, featuring a welcoming front porch with rocking chairs and vibrant seating. Lush plants in decorative pots frame the entrance. The exterior is painted in soft grey tones, complemented by white shutters and a serene pathway leading to the door.

Cottage in Palm Harbor

4.85 out of 5 average rating, 99 reviews

Happy Camper Cottage | Cozy Oasis with Hot Tub

Top guest favorite

A bright and airy seating area features a hanging chair and a cozy sofa, adorned with colorful cushions. Natural light floods in through large windows, complemented by light-toned wooden flooring and a textured pink area rug that adds warmth to the space.

Cottage in Largo

4.98 out of 5 average rating, 66 reviews

Family FUN~Pool, GameRoom+Bikes, Near Beach/Trail

A bright studio space features a spacious king-size bed and a cozy sofa in soft blue tones. Natural light filters through window treatments, highlighting white walls and wooden beams that add warmth. A mirror and wall decor complement the relaxing atmosphere, while a TV is mounted nearby.

Cottage in Siesta Key

4.91 out of 5 average rating, 67 reviews

Cozy Cottage 1 block from Beach

Top guest favorite

An open living area features tiled flooring and soft lighting, with comfortable seating arrangements including a sofa and armchairs. A dining area is visible, showcasing a wooden table with chairs. Decorative touches such as artwork and a side cabinet enhance the space's charm.

Cottage in Sarasota

4.99 out of 5 average rating, 96 reviews

Quaint Cottage,150 steps away from Crescent Beach!

A private backyard space features a hot tub with a bubbling water feature, surrounded by a paved patio. A dining table with chairs is positioned nearby, catering to outdoor meals and relaxation. Lush greenery and landscaping enhance the tranquil environment.

Cottage in Bradenton

4.91 out of 5 average rating, 77 reviews

Sandy Cottage w/ Hot Tub, 20 min to Beach + Garden

Pet-friendly cottage rentals

Cottage in Tampa

4.76 out of 5 average rating, 171 reviews

Good Vibes Cozy Cottage on Million $ Row

Top guest favorite

A cozy living room features a tan sofa positioned across from a purple armchair. A round coffee table is centered on a light-colored rug. Colorful artwork adorns the wall, while a floor lamp provides warm lighting. The space is brightened by natural light through a window.

Cottage in St. Petersburg

4.95 out of 5 average rating, 124 reviews

Artsy guest house; near downtown w/ private patio

A serene sunset over the Little Manatee River is captured, with vibrant hues of orange and pink reflecting on the water surface. The dark outline of trees defines the horizon, creating a peaceful natural backdrop.

Cottage in Ruskin

4.92 out of 5 average rating, 123 reviews

Little Manatee River Cottage

Top guest favorite

Cottage in Tampa

4.97 out of 5 average rating, 222 reviews

Bay Lake Cottage

Top guest favorite

A single-story cottage features a pink exterior with large windows allowing natural light. A landscaped garden with decorative stones is visible in the front. White chairs are placed near the entrance, and ample parking spaces are provided in the driveway.

Cottage in Indian Rocks Beach

4.9 out of 5 average rating, 307 reviews

Vintage Florida Beach Cottage B

A charming cottage exterior is highlighted by vibrant blue accents on the door and window frames. Lush palm trees surround the property, and a pathway of red bricks leads to the entrance. Gravel landscaping complements the home, enhancing its welcoming appearance.

Cottage in Indian Rocks Beach

4.7 out of 5 average rating, 218 reviews

Beachy Paradise

Top guest favorite

A welcoming living area features a comfortable blue couch adorned with throw pillows. A wooden coffee table with decorative items sits atop light wood flooring, alongside a woven basket and a pouf. In the background, a bright dining area is visible, accompanied by a modern kitchen.

Cottage in Dunedin

4.99 out of 5 average rating, 344 reviews

Walk to Downtown and Waterfront - Private Yard

Top guest favorite

A row of brightly colored Adirondack chairs is positioned on the sandy beach, facing the tranquil ocean. The hues include yellow, orange, green, blue, pink, and purple. A clear blue sky with soft clouds complements the serene shoreline.

Cottage in Nokomis

4.98 out of 5 average rating, 164 reviews

Staycation Sanctuary

Private cottage rentals

The single-family beach cottage features a light yellow exterior with red accents and three prominent windows. Surrounding the home, palm trees and landscaping provide a lush atmosphere. A paved area holds several designated parking spaces in front of the cottage, with a stone picnic table nearby.

Cottage in Madeira Beach

4.85 out of 5 average rating, 142 reviews

Family Friendly Beach Cottage in Madeira Beach, FL

Top guest favorite

The living room features modern teal leather seating, including a spacious sofa and two armchairs, arranged to encourage conversation. Natural light filters in through two windows, adorned with patterned curtains. A door with clear glass inserts leads outside, enhancing the room's openness.

Cottage in Treasure Island

4.99 out of 5 average rating, 217 reviews

Island Time Stay: Sunrise

A comfortably furnished living area features a neutral sofa adorned with patterned pillows. Two geometric wooden tables are positioned in front, with a single armchair nearby. Light wood ceilings enhance the bright atmosphere, while decorative artwork is displayed on the wall.

Cottage in Holmes Beach

4.97 out of 5 average rating, 38 reviews

Sailfish Gulf Suites #4, Garden Views, Steps from

A bright and airy living space is shown, featuring a contemporary sofa facing a soft beige wall and natural wood accents. A stylish dining area with rattan chairs is visible in the foreground, adorned with dishes and a decorative centerpiece. Large windows allow ample natural light.

Cottage in Bradenton

4.98 out of 5 average rating, 42 reviews

*Fall Special* NEW 3BR | Near AMI, IMG & Beach

Top guest favorite

A family beach house is showcased, featuring a main structure with a covered porch and large windows. Adjacent is a smaller cottage. Both buildings have a light-colored exterior and are surrounded by soft sandy ground and palm trees, highlighting the beachfront location.

Cottage in Indian Rocks Beach

4.96 out of 5 average rating, 27 reviews

Kamp Komfort Historic Family Beach House

Top guest favorite

A cozy dining area is framed by large windows, offering a direct view of the beach and ocean. Two light-colored chairs surround a round wooden table. Outside, lounge chairs are positioned on the sand, with stunning sunset colors reflecting on the water.

Cottage in Indian Shores

4.88 out of 5 average rating, 199 reviews

*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*

A porch area features two wooden Adirondack chairs positioned on a wooden surface. A colorful area rug lies beneath them, and large windows provide a view into the interior. Lush greenery is visible in the background, creating a serene environment.

Cottage in Bradenton

4.89 out of 5 average rating, 9 reviews

Charming downtown cottage

Top guest favorite

An enclosed sitting area features a comfortable daybed adorned with colorful throw pillows against light wooden paneling. A small blue table accompanies the seating, with large windows allowing natural light to illuminate the space while offering views of the surrounding greenery.

Cottage in Osprey

4.97 out of 5 average rating, 66 reviews

Mattie’s Cottage by the Bay

Luxury cottage rentals

The living area features a high, wooden ceiling with a decorative octagonal window, allowing natural light to fill the space. Comfortable seating includes a blue sofa and a floral-patterned chair, positioned near large windows that frame views of the outdoor patio.

Cottage in Indian Rocks Beach

4.78 out of 5 average rating, 36 reviews

Yachtsman Gulf front on sand, Sleeps 6 Heated Pool

A charming cottage is showcased behind a white picket fence, surrounded by tropical landscaping featuring palm trees and green foliage. A gravel driveway leads towards the entrance, and a covered porch is visible, enhancing the welcoming appearance of the home.

Cottage in Siesta Key

4.92 out of 5 average rating, 83 reviews

Location 3 Bed Cottage 1 block to SiestaKey beach

A beachfront view reveals a secluded area with soft sand and lush tropical vegetation leading to a covered patio. Palm trees frame the scene, with the inviting exterior of the cottages visible in the background under a clear blue sky.

Cottage in Indian Rocks Beach

4.5 out of 5 average rating, 10 reviews

3 Palms Beachfront Cottages - Beachfront

The exterior of the cottage is shown, featuring a light-colored facade and a peaked roof. Lush greenery surrounds the front, including tall tropical plants. Large windows allow natural light to enter, while a blue accent decoration adds a touch of color.

Cottage in Clearwater

4.92 out of 5 average rating, 60 reviews

Seashell Cottage

An outdoor entertainment area features wicker seating arranged around a glass-top coffee table. The space includes a dining table and chairs, with a view of the private pool surrounded by lush greenery. Light filters through the open space, creating a relaxing atmosphere.

Cottage in Holmes Beach

4.89 out of 5 average rating, 9 reviews

Updated Home, 5 Houses from the Beach! Private

A serene waterfront view captures the calm water reflecting the blue sky and scattered clouds. Palm trees line the shore, adding greenery to the scene, while wooden posts stand in the water, hinting at nearby docks and boats.

Cottage in St. Pete Beach

5 out of 5 average rating, 21 reviews

Pass-a-Grille Historic Cottage Duplex

A dining table with a circular design is set on a wooden deck, accompanied by four woven chairs. The space overlooks the bay, with calm water visible beyond the railing and greenery in the background, creating a peaceful outdoor setting.

Cottage in Longboat Key

Family Time: 4BR Cottage with Bay Views

Top guest favorite

A private heated pool is framed by lush tropical landscaping, presenting a serene setting. Multiple white lounge chairs surround the pool, complemented by a dining table. Nearby, vibrant greenery enhances the tranquil atmosphere under a clear blue sky.

Cottage in Anna Maria

4.96 out of 5 average rating, 26 reviews

Charming cottage w/heated pool in prime location.

Quick stats about cottage rentals near Anna Maria Island

Total rentals
70 properties
Nightly prices starting at
ﺩ.ﺇ441 before taxes and fees
Total number of reviews
2.8K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
30 properties have a pool

Destinations to explore