Cottage holiday rentals in Bradenton

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.

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.

4.87 out of 5 average rating, 102 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.

4.96 out of 5 average rating, 164 reviews

A spacious backyard is featured, bordered by a wooden fence for privacy and lined with tropical plants and trees. A concrete patio area is included, which features a grill covered for protection. The lawn is open and well-maintained, providing a serene outdoor space.

Cottage in Gulfport

The Pelicans Roost / Gulfport

The Pelicans Roost is a remodeled home, with a new fully stocked kitchen with all your cooking and entertaining needs. All new furnishings, a screened in back porch and a patio with an outside table and grill. The yard is completely fenced and lined with tropical plants and trees for your privacy. This spacious and comfortable home is clean and in a quiet neighborhood just 5 blocks from all that downtown Gulfport has to offer- the Marina,Beach,Restaurants, Shops, Fishing, Galleries and more...!

Cottage in Seminole Heights

4.95 out of 5 average rating, 406 reviews

Lovely Loft Close to Everything in Tampa

A perfect balance between suburban serenity & urban convenience in this historic Tampa neighborhood. Central air, Roku, strong Wi-Fi, coffee, tea, snacks. Easy self-check-in. The ideal home base for your Tampa adventures. Quick 10 min drive to TPA Airport, Busch Gardens, Fla Amphitheater, Raymond James Stadium, Aquarium, Cruise Port, USF, UT, Ybor City, Armature Works & Downtown. 35 min to countrys best beaches, 70 min to Orlando. Plus great restaurants & breweries within walking distance.

4.99 out of 5 average rating, 135 reviews

The cottage features a welcoming front porch adorned with vibrant flowers and lush greenery. A stone pathway leads to the entrance, framed by well-maintained landscaping. Large windows allow ample natural light, enhancing the charm of the remodeled exterior.

Cottage in Tampa

Wonderful 2-Br, 2 Bath Cottage near the river.

Welcome to my little cottage in the city. The house was built in 1926 but has been fully remodeled with modern style, while keeping the charm of an older home. Even though it's close to everything Tampa has to offer, it still has the feeling of that little, quiet neighborhood near the river. This is my get away home. I love the front porch to sit on with a cold beverage and watch neighbors stroll by walking their dogs. The river park is very close by which is a nice walk from the cottage.

Cottage in Euclid Place - St. Paul

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.

4.95 out of 5 average rating, 125 reviews

Artsy guest house; near downtown w/ private patio

This uniquely decorated guest house is a private oasis with a lovely, private patio. The house is decorated with Latin American art from the owner's collection & travels. Only 11 blocks to downtown and very close to grocery stores, art galleries and all the night light life St. Pete offers. The home has a full kitchen and a very comfortable bedroom for one or two people. A perfect location for those that want to experience a comfortable and relaxing place. Only 12 block walk to Tropicana.

Superhost

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 Indian Beach-Sapphire Shores

4.8 out of 5 average rating, 268 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 circular pool is surrounded by a landscaped area featuring vibrant plants and red stones. Lounge chairs offer seating nearby, while a shaded umbrella provides relief from the sun. Inflatable rings float in the clear water, and a view of the canal can be seen in the background.

4.94 out of 5 average rating, 136 reviews

Waterfront+Pool+Putting Green+Beach Gear! 2BR/2BA

• Perfect for couples, families, or remote work escapes • Unwind by the water • Fish from dock • Well equipped kitchen (no food items) • Starter supplies: coffee, tea, paper goods & toiletries • 2 bd / 2 ba • Selfie Wall • Keyless Entry • Pool • Putting Green *Tap the 🖤 in the corner to save this listing and find it faster later* • 10 miles to beach, *Award Winning Ana Maria Island • 7 miles to IMG Academy • 11 miles to SRQ Airport • 2 miles from Pittsburgh Pirates Training Camp

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, 215 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.

Cottage in Bellevue Terrace

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.

4.93 out of 5 average rating, 135 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.

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, 121 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.

4.9 out of 5 average rating, 366 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.

Popular amenities for cottage rentals in Bradenton

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

The entryway features warm wooden floors and natural light streaming through large windows. A vibrant blue door adds a pop of color, while a stylish desk and lamp provide a functional workspace. A wooden cabinet with glass doors showcases decorative items and greenery.

4.94 out of 5 average rating, 49 reviews

Charming Home w/ Hot Tub, 20 min to Beach + Garden

4.96 out of 5 average rating, 195 reviews

A spacious outdoor deck is shown, featuring a hot tub covered with a protective lid. Blue and white lounge chairs, along with bright cushions, are arranged for relaxation. The cottage's vibrant turquoise exterior is complemented by a cheerful yellow door and lush surrounding greenery.

Cottage in Safety Harbor

Harbor Oasis | Hot Tub | Private | Lush Backyard

4.94 out of 5 average rating, 65 reviews

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

Close to the Beach+ Private heated pool and spa!

Superhost

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.

Cottage in Clearwater Beach

4.78 out of 5 average rating, 162 reviews

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

4.98 out of 5 average rating, 66 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

4.91 out of 5 average rating, 69 reviews

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

Cozy Cottage 1 block from Beach

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.

4.99 out of 5 average rating, 97 reviews

Quaint Cottage,150 steps away from Crescent Beach!

An aerial view captures the expansive Siesta Key coastline, showcasing a stretch of sandy beach meeting calm blue waters. Nearby buildings and lush greenery punctuate the landscape, highlighting the serene environment just minutes away from the cottages.

4.78 out of 5 average rating, 144 reviews

Siesta Key Cottages Crescent 1B Beach/Pool/Hot Tub

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.

4.76 out of 5 average rating, 173 reviews

Cool Breeze Cottage by the Bay in South Tampa

5 out of 5 average rating, 20 reviews

A bright living area features terracotta tile flooring and large windows allowing natural light to fill the space. A round dining table is set for four, while a comfortable seating area includes a light green sofa and a decorative side table. Tropical decor enhances the ambiance.

Cottage in Holmes Beach

Palm Villa by Beach Boutique Rentals

4.94 out of 5 average rating, 18 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

Cottage in Indian Rocks Beach

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.

4.7 out of 5 average rating, 218 reviews

Beachy Paradise

4.93 out of 5 average rating, 87 reviews

A cozy living space features a dark leather couch and a decorative wooden coffee table. Natural light streams through large windows adorned with blue patterned curtains. A flat-screen TV is mounted on the wall, and a wooden cabinet displays nautical-themed decor.

Cottage in Riverview

Alafia River Cottage

4.99 out of 5 average rating, 280 reviews

The cottage exterior features a light teal facade with white trim and multiple windows allowing natural light. A welcoming front porch includes a central entry door flanked by two large windows. The address is displayed prominently above the door. Lush greenery surrounds the base of the structure.

Cottage in Gulfport

Gulfport Art District - One Block From Beach!

Cottage in Indian Rocks Beach

A spacious living area features a large sectional sofa in a neutral tone, accented by coastal-themed artwork on the walls. Light wood flooring complements the room, which includes a dining table and two bar stools, allowing for casual seating options. Bright natural light floods the space.

4.91 out of 5 average rating, 129 reviews

ALL NEW! Coral Sands II ~Coastal Modern 2/2 IRB

Cottage in Bradenton Beach

A two-story elevated property is shown with a wooden exterior painted in light tones. A spacious deck with blue accents overlooks the ground level, which features a sandy area bordered by greenery. Steps lead up to the entrance, providing access to the living space.

4.85 out of 5 average rating, 101 reviews

AMI Tree House

Private cottage rentals

Cottage in Indian Beach-Sapphire Shores

A screened lanai is presented with light-colored wicker furniture, featuring green striped cushions. A small coffee table is positioned between the two seating areas, and a bicycle can be seen tucked in the corner, complementing the lush garden views visible through the screens.

4.8 out of 5 average rating, 66 reviews

Walk to Bay light filled private Cottage King bed

4.96 out of 5 average rating, 72 reviews

A welcoming porch area features a small round table and two chairs under a shaded awning. A hanging planter with vibrant flowers adds color. Lush greenery lines the perimeter, and a path of natural mulch leads away from the entrance.

Cottage in Tampa

Tranquil Guesthouse Hideaway (Near MacDill AFB)

The living room features a spacious sectional sofa and a central round coffee table. A ceiling fan is present above, and natural light enters through large windows adorned with patterned curtains. A desk and chairs provide workspace, while art and decor enhance the inviting ambiance.

4.93 out of 5 average rating, 42 reviews

Historic Cocoanut Art Cottage

The entrance features a charming porch with a white front door framed by tall windows on either side. A simple welcome mat lies in front of the door, and colorful landscaping with plants and red foliage completes the inviting exterior.

4.98 out of 5 average rating, 83 reviews

Central Quiet Bright Cottage, near Skyway Bridge.

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.

4.91 out of 5 average rating, 45 reviews

Aqua Breeze Cottage - Winter retreat 2 bd, 2 ba

Superhost

A charming beachfront bungalow features a mint green exterior with a vibrant door, surrounded by well-maintained landscaping. The front yard is enclosed by a white picket fence, with tropical plants and decorative stones enhancing the inviting atmosphere.

4.58 out of 5 average rating, 12 reviews

Chic Peaceful 3BD Cottage - Walk to Siesta!

4.97 out of 5 average rating, 31 reviews

A bright living area features a comfortable seating arrangement with a light-colored sofa and armchair, complemented by decorative pillows. A coffee table sits centrally, and a television is mounted on a white console. Natural light flows in through large windows, with views of the outdoor patio visible.

Cottage in Holmes Beach

Sailfish Gulf Suites #2, Beachfront, Steps to the