Cottage holiday rentals in Bradenton

4.96 out of 5 average rating, 107 reviews

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

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 sparkling pool reflects sunlight, set against a backdrop of lush greenery. Two blue chairs are positioned near a small table on grass, offering a serene view of the adjacent canal. A decorative fence surrounds the backyard, enhancing the outdoor space's privacy.

4.94 out of 5 average rating, 148 reviews

Waterfront Stay•Pool • PingPong • Near AMI Beaches

Your peaceful waterfront escape awaits. This cozy 2BR/2BA cottage offers two living areas. The bright Florida room overlooks the canal. It includes areas for a game of ping pong, a life‑size Jenga set, watching tv, having a bite at the table, and a sleeper sofa. Enjoy morning coffee at the dock watching the fish jump or grab your pole. Relax by the sunny pool or practice on the putting green ⛳. Fast WiFi, a dedicated workspace, beach gear, and a full kitchen make winter stays easy and relaxing.

4.88 out of 5 average rating, 110 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.

4.85 out of 5 average rating, 129 reviews

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 Cove

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."

Cottage in Bradenton Beach

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.

4.97 out of 5 average rating, 226 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.

4.98 out of 5 average rating, 100 reviews

A charming cottage is surrounded by lush greenery, featuring a covered porch adorned with blue rocking chairs and a decorative whale motif. Tropical plants frame the view, while a wooden fence adds to the property’s privacy and character.

Cottage in Gulfport

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.

4.99 out of 5 average rating, 204 reviews

Luxury Beach Cottage | Walk to Dining & Sunset

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

4.98 out of 5 average rating, 102 reviews

Cottage in Cove

Cortez ~ Grouper Cottage. BRING YOUR BOAT!

This waterfront home with private dock and boat slip is the perfect place to get away. Grouper Cottage is an ideal cozy place to unwind and enjoy sunsets and dolphins. You will fall in love with this refurbished historic cottage. Private setting offering tranquility, with picturesque palm trees and mangroves surrounding the property's shoreline. Cortez dockside cottages is nestled on an acre with a compromise of old Florida with the historical background a laid back Island vibe.

A mobile home with a welcoming front porch is surrounded by lush greenery and colorful flowering plants. The structure features a light exterior, complemented by a decorative element above the porch. A carport for vehicle parking is visible, alongside a well-maintained pathway.

4.97 out of 5 average rating, 124 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.

Cottage in Bradenton Beach

4.9 out of 5 average rating, 192 reviews

Ohana Gulfside C Historic 1 Bed - 250 ft. to Beach

COMPLETELY REMODELED! Aloha and welcome to our bit of old Florida. Ohana Hale Gulfside is 250 feet to the white sand beaches and turquoise water. Come join us for your vacation in the sun. The ideal bungalow for a couple or small family. This one bedroom, one bath with kitchenette is made for your best vacation memories. This unit is only one block to the beach and one block to the Bridge Street shopping district and the pier! This unit is one-pet friendly.

4.9 out of 5 average rating, 377 reviews

Serene Suite*Walk 2 Dwtn/Riverfront/Dining*AMI*IMG

Our private, old Florida, suite located in historic downtown Bradenton with spacious back deck, king bed, sitting area, kitchen, fast FREE WiFi & parking. Walk to the Riverfront where you will enjoy dining, shopping and some amazing waterfront views. Just minutes to AMI beaches, shops, and endless fun. Walkable to local museums, Planetarium, IMG and other local favorites. Nestled in a quiet neighborhood this suite makes for an enjoyable, peaceful stay.

Cottage in Bellevue Terrace

4.93 out of 5 average rating, 138 reviews

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. 🌴

Popular amenities for cottage rentals in Bradenton

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.98 out of 5 average rating, 42 reviews

Beachy Keen Cottage A only steps to the Beach

4.88 out of 5 average rating, 149 reviews

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

Sunny - Key West Vibe Cottage - Pool - Walkable

4.91 out of 5 average rating, 105 reviews

A private hot tub is positioned on a wooden deck, outfitted with two black chairs and a small table. The cottage features a light blue exterior with a white door framed by two towels. A pergola with climbing plants is visible in the background.

Cottage in Safety Harbor

Heart of Safety Harbor | Hot Tub | Luxe Comfort

Cottage in Clearwater Beach

The exterior view of a charming blue cottage is presented, featuring white accents and shutters. Two light-colored lounge chairs are positioned on the paved front area. Lush greenery surrounds the property, enhancing the inviting beach house vibe.

4.79 out of 5 average rating, 168 reviews

Corner Cottage Sleeps 5, Steps to Beach, Pets OK.

4.99 out of 5 average rating, 72 reviews

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

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

4.89 out of 5 average rating, 44 reviews

Cottage in Palm Harbor

Cozy Cottage Near Beach | Hot Tub • Pet Friendly

The exterior of the cottage displays a vibrant yellow wall and white siding. A wooden deck extends from the property, surrounded by greenery. An outdoor light fixture is visible next to the door. The backdrop includes a taller building with a tiled roof.

5 out of 5 average rating, 17 reviews

Beachside Historic Cottage "Dunes" – Steps to Sand

Superhost

4.9 out of 5 average rating, 79 reviews

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

Pet-friendly cottage rentals

Cottage in Bayshore Beautiful

A comfortable seating area features two light-colored sofas with throw pillows, arranged around a rustic wooden coffee table. A decorative screen provides partial division from other spaces, and a textured rug is laid beneath the furniture, enhancing the warm ambiance of the room.

4.78 out of 5 average rating, 188 reviews

Gasparilla Bayshore Good Vibes cottage

Superhost

The front view of the bungalow features a welcoming entrance framed by tall palm trees. The light blue exterior contrasts with the lush greenery surrounding the property. A driveway leads to the entrance, inviting visitors to explore the charming cottage just steps away from the beach.

Cottage in Sarasota

4.89 out of 5 average rating, 9 reviews

Charming 2BD Bungalow Close to Crescent Beach!

4.83 out of 5 average rating, 135 reviews

Coral Sands I -2/2 Porch, Pool Tbl, Best Location!

4.91 out of 5 average rating, 23 reviews

A cozy deck is featured with two chairs and a hammock, overlooking the peaceful landscape. Strings of lights enhance the space, while the sky transitions from blue to dusk. Nearby, views of open fields can be seen, creating a tranquil outdoor retreat.

Cottage in Myakka City

New Country Cottage on Lake Manatee Lakewood Ranch

An aerial view highlights the river house set amid lush greenery, featuring a large wooden deck and fenced yard. The property is bordered by the Braden River, with its tranquil waters reflecting the surrounding trees and homes.

4.96 out of 5 average rating, 53 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

A wooden deck extends from the cottage, featuring a sturdy chair positioned for relaxation. The light blue exterior of the house contrasts with the greenery surrounding the space. Steps lead up to the deck, enhancing accessibility to the entrance.

4.87 out of 5 average rating, 70 reviews

Cozy Cottage

4.86 out of 5 average rating, 381 reviews

A cozy interior space features a neutral color palette with a striped bedspread. A serving tray holds two white cups beside a small dish of candy. Natural light fills the room, highlighting a kitchenette in the background, complemented by white cabinetry and a subtle decor.

Cottage in Dunedin

Cozy up in a French Country nest NEAR EVERYTHING

5 out of 5 average rating, 36 reviews

A cozy living area features a light grey sofa adorned with throw pillows, complemented by two round coffee tables. A floor lamp and a potted plant add warmth. Natural light floods the room through large windows, enhancing the welcoming atmosphere.

Cottage in Holmes Beach

Hibiscus Villa by Beach Boutique Rentals

Private cottage rentals

4.85 out of 5 average rating, 151 reviews

A spacious heated pool is visible, reflecting sunlight under a clear blue sky. Surrounding palm trees and lounge chairs are arranged around the pool area, with umbrellas providing shade. The beach is noticeable in the background, creating a relaxed coastal ambiance.

Cottage in Madeira Beach

Family Friendly Beach Cottage in Madeira Beach, FL

4.94 out of 5 average rating, 51 reviews

Cottage in Sarasota

Historic Cocoanut Art Cottage

4.75 out of 5 average rating, 164 reviews

A spacious saltwater pool is surrounded by lounge chairs on a paver deck. Palm trees offer shade in the background, and a bright blue sky is overhead. The multi-story building can be seen in the distance, providing a backdrop to the leisure space.

Cottage in Sarasota

Drift Inn A Heated Pool & Private Beach Access!

The exterior of a modular home is showcased, featuring a covered porch with two chairs under a sloped roof. Lush plants and palm trees surround the entrance, and a paved driveway leads to the home. Clear blue skies provide a bright backdrop.

4.94 out of 5 average rating, 78 reviews

Cheerful 2 bedroom , plus bunk room vacation home.

The charming cottage features a white picket fence leading to a front porch adorned with floral details. Lush greenery surrounds the home, with small rock pathways and a mix of trees offering shade. A comfortable seating area is positioned on the porch.

4.96 out of 5 average rating, 28 reviews

Artsy 1930s Cottage - walk to LECOM & waterfront

4.93 out of 5 average rating, 54 reviews

The exterior of a brightly colored cottage features a pale blue facade with navy blue shutters and a welcoming front porch. A U.S. flag is displayed on the porch, while lush greenery surrounds the home. A driveway provides access to an open carport.

Cottage in Palmetto

Aqua Breeze Cottage - Winter retreat 2 bd, 2 ba

An inviting front entrance features light green siding and a modern white door. Two comfortable chairs with decorative cushions are placed beside the entrance, while natural light is welcomed through the large windows. A doormat with the word 'hello' is positioned at the doorway.

4.98 out of 5 average rating, 49 reviews

Stylish Cottage Near IMG & Beach

A wooden deck is positioned near the beach, surrounded by soft sand. A palm tree stands nearby, providing shade. The structure features large windows, allowing light to fill the space. A view of the Gulf of Mexico is visible, with gentle waves lapping at the shore.