Cottage vacation rentals in Bradenton Beach

4.96 out of 5 average rating, 106 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.

4.85 out of 5 average rating, 127 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."

4.85 out of 5 average rating, 147 reviews

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

Family Friendly Beach Cottage in Madeira Beach, FL

Mad Beach Cottage is a single family home in the Surf Song Resort on Madeira Beach 60 flip-flop steps to SAND! No streets, boardwalks or stairs! You'll enjoy a heated pool, 3 Weber grills, shuffleboard and sundeck with lounge chairs for gazing at spectacular sunsets every night. It's located across from famous John's Pass Fishing Village Boardwalk for shopping, dining, ice cream, coffee, live music, brew pubs, dolphin/fishing/sunset/pirate boat cruises, wave runner/kayak rentals. 5* LOCATION!

Cottage in Indian Rocks Beach

A vibrant tropical mural featuring large flowers adds a pop of color to the room, while a cozy seating area includes a sofa adorned with decorative pillows. A small dining table with tropical-patterned chairs provides a space for meals. The outdoor area showcases a lit pool, creating a serene evening ambiance.

4.99 out of 5 average rating, 196 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!

Cottage in Indian Beach-Sapphire Shores

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.

4.8 out of 5 average rating, 275 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, 144 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 Indian Rocks Beach

A sandy path leads from a grassy area to the shoreline, flanked by light vegetation. The vibrant blue sky is dotted with clouds, while the gentle waves of the ocean are visible in the distance.

4.76 out of 5 average rating, 117 reviews

#5 Beach Front Cottage w view- Indian Rocks Beach

LOCATION, location! Closest beach cottage to the water at Indian Rocks beach, view of the water from your porch & easy access to grass for pets. Perfect couples getaway. Enjoy some of Florida’s best beaches. Minimalistic living. *Kitchen recently updated* Shared gazebo & picnic table next door. Shared Washer & dryer takes quarters. Walking distance to local restaurants and bars. Minutes away from Clearwater beach, tourist attractions and mini golf. Property located next 2 public access.

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.

Cottage in Bradenton Beach

4.97 out of 5 average rating, 158 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!

4.91 out of 5 average rating, 369 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 Bradenton Beach

A vibrant yellow cottage is surrounded by a sandy area with palm trees. Colorful adirondack chairs in pink, blue, and green are positioned on the white gravel. A covered outdoor seating area is visible to the side, enhancing the beachside environment.

4.99 out of 5 average rating, 219 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.

Cottage in Bradenton Beach

4.88 out of 5 average rating, 293 reviews

One Block to Beach - Ohana Hale Beachside 2 BR

COMPLETELY REMODELED February 2025! Aloha and welcome to our Island Home Ohana Hale AMI! Our home is designed for the ultimate beach vacation experience, featuring 2 cozy bedrooms and 1.5 baths. The open kitchen and living area create a spacious, inviting atmosphere, perfect for relaxation and fun. Be sure to check out our amazing 3rd-floor shared deck—it's the perfect place to watch stunning sunsets over the Gulf of Mexico.

Popular amenities for Bradenton Beach cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Indian Rocks Beach

4.98 out of 5 average rating, 42 reviews

Beachy Keen Cottage A only steps to the Beach

4.94 out of 5 average rating, 68 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!

4.91 out of 5 average rating, 103 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.

4.78 out of 5 average rating, 164 reviews

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

4.99 out of 5 average rating, 69 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

4.99 out of 5 average rating, 98 reviews

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

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.

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 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.

4.77 out of 5 average rating, 179 reviews

Cool Breeze Cottage by the Bay in South Tampa

5 out of 5 average rating, 5 reviews

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

Charming 2BD Bungalow Close to Crescent Beach!

Cottage in Independence Square

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.

4.76 out of 5 average rating, 37 reviews

Yachtsman Beachfront Cottage w/ Heated Pool

4.96 out of 5 average rating, 167 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

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, 129 reviews

Artsy guest house; near downtown w/ private patio

5 out of 5 average rating, 15 reviews

Cottage in Siesta Key

House with pool 1 block to village, 3blks to beach

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, 48 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

4.95 out of 5 average rating, 215 reviews

Cottage in Dunedin

Perfect Location Cottage in Delightful Dunedin

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.

4.81 out of 5 average rating, 68 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)

5 out of 5 average rating, 8 reviews

The cottage exterior features a light blue facade with a centered front door, flanked by two large windows. A small porch with a bench is present, along with potted plants. A single-car garage is visible, and a manicured lawn surrounds the home.

Cottage in Sarasota

Cottage & Tree ~ by the Sea

5 out of 5 average rating, 15 reviews

A welcoming living area features a light-colored sectional sofa with decorative pillows and a contrasting green area rug. Large windows provide views of the outdoor patio, while a flat-screen TV is mounted against the wall. Lush plants and modern decor complete the space.

Cottage in Holmes Beach

Sailfish Gulf Suites #1, Beachfront, Steps to the

4.98 out of 5 average rating, 83 reviews

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.

Cottage in Palmetto

Central Quiet Bright Cottage, near Skyway Bridge.

4.92 out of 5 average rating, 49 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

A spacious screened lanai features comfortable seating options, including wicker chairs and a sofa with striped cushions. Natural light fills the area, creating a bright ambiance, while plants and decorative accents enhance the setting. A wide pocket sliding door connects the lanai to the family room.

4.95 out of 5 average rating, 57 reviews

Discover Hidden Cove #2 - Water Views with Privacy

The exterior of a light blue house is framed by a manicured lawn featuring lush greenery and colorful plants. Two wooden chairs sit on the porch, providing a welcoming space to relax. Large windows allow natural light to fill the interior.