Guesthouse vacation rentals in Bradenton

Guesthouse in St. Petersburg

A private patio area is surrounded by wooden fencing adorned with greenery. Two blue chairs are positioned at a round table, creating a serene space for relaxation. Natural light filters through the nearby trees, enhancing the inviting atmosphere of the outdoor setting.

4.97 out of 5 average rating, 239 reviews

Cozy Guesthouse Near Downtown (Non-Toxic)

Come relax in this calm, newly renovated guest suite. Clean, natural, & chemical free - diffusers and oils available on site. Amenities like central a/c, laundry, private patio, full kitchen, Netflix & Hulu. A short 5 minute drive from downtown - near tons of local restaurants, entertainment, and beaches. St. Pete loves the local vibe, be sure to check out our visitors guide for suggestions on spots to see while you’re here. It doesn’t get any better than St Pete! Book your stay with us today!

A private stock tank pool is surrounded by a wooden deck and lounge chairs. An umbrella provides shade over the pool area. Colorful towels and a stylish table with refreshments are visible, set amidst a landscaped courtyard with lush greenery.

4.99 out of 5 average rating, 236 reviews

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

A spacious bedroom features a king-size bed adorned with a blue and white textured coverlet. Soft natural light filters through the window, illuminating the room, which includes a nightstand, dresser, and a comfortable bench at the foot of the bed.

4.97 out of 5 average rating, 287 reviews

Sarasota guest house only 8 miles to Siesta Key

Our Florida-themed guest house has everything you need to enjoy your vacation in beautiful Sarasota, Florida. It is a very comfortable, clean and private one bedroom and one bathroom guest house. It is a completely separate space and has it's own private entrance. It is conveniently located in a quiet, safe neighborhood near Interstate I-75, Shopping, Dining, Twin Lakes Park, Serenoa Golf Course, Myakka River State Park and just 8 miles from the #1 beach in the U.S. - Siesta Key Beach.

A charming entrance features a white trellis adorned with vibrant pink bougainvillea, offering a welcoming touch to the greenery surrounding the cozy cottage. A stone pathway leads to the front door, enhancing the inviting atmosphere of this secluded garden.

4.93 out of 5 average rating, 198 reviews

1920s Cottage in a Private Tropical Wooded Setting

Your perfect Sarasota getaway! This lovely little cottage is very private & isolated but just minutes from downtown. Modern conveniences & comfort nestled in a charming and cozy period cottage. You will make yourself at home in this tranquil, cozy, and quaint 1920's Old Florida Guest House. Nestled under a canopy of ivy-covered oaks, pines and the tallest of palms - where the flowers are always in bloom! This captivating cottage is your woodsy home base for all your Sarasota adventures!

A spacious living area features a billiard table, a sectional sofa, and a kitchen area with wooden cabinetry and modern appliances. Natural light is provided by ceiling lights and side windows, set against a neutral grey wall.

4.84 out of 5 average rating, 458 reviews

Spacious guest suite near the bay, IMG, Anna Maria

This condo is attached to my home but is totally independant with private access. The condo is upstairs and accessible by a spiral staircase ( avoid large suitcase, may be challenging for some people) A large bedroom with a queen bed, an equiped kichen ( combined microwave/ oven), a bathroom ( large shower) and a living room with high ceiling. We follow cleaning recommendations. You can arrive anytime after check in time.PARKING is in the dead end street in front of my garden

Guesthouse in Gillespie Park

An outdoor area is shown with a walkway made of red pavers leading to a yellow building. A dining set with an umbrella is situated on a gravel surface, surrounded by potted plants. Decorative stones and landscaping enhance the inviting outdoor space.

4.91 out of 5 average rating, 150 reviews

Perfect Florida location: Craftsman Carriage House

Beautiful, recently built accessory dwelling in downtown Sarasota designed to match and complement our historic 1920s bungalow main house, which can be booked separately on AirBnB. The 1BR/1BA carriage house apartment has all modern amenities, with a dedicated garage parking spot and a lovely outdoor porch. The carriage house features Craftsman-style details and is available for short- or long-term stays. Locally-based property management team on-call to ensure a pleasant stay.

Guesthouse in Bradenton Beach

A vibrant yellow cottage is depicted with a landscaped area featuring palm trees and a gravel yard. Colorful adirondack chairs in pastel shades of pink and blue offer seating options, creating a casual outdoor space. Nearby cottages are visible, enhancing the beachfront setting.

4.99 out of 5 average rating, 191 reviews

Bradenton Beach Sunsets 1, 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.

A light blue bedroom features a spacious bed with a floral-patterned blanket and a ceiling fan overhead. Double glass doors provide a view of the pool area outside. Storage options include a white dresser and closet, while a small table and chair are positioned nearby.

4.99 out of 5 average rating, 142 reviews

Maggie's Hideaway

This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!

The cozy living room features a comfortable sofa and a sleek armchair, complemented by a decorative rug. A glass coffee table sits in the center, while a wall-mounted TV displays a scenic beach view, enhancing the serene atmosphere.

4.89 out of 5 average rating, 137 reviews

Secluded Retreat 25 min from the best beaches!

Escape to our charming getaway, nestled more than 1000ft off the main road. This private home is just 25-30 minutes away from the stunning Gulf Coast beaches from Anna Maria Island all the way down to Siesta Key Beach. You'll also find yourself close to popular destinations such as IMG Academy, Freedom Factory, St. Armands Circle, and a variety of local amenities and great dining, making it ideal for both relaxation and exploration.

A modern living area features a dark sofa draped with a light throw blanket, paired with a wooden table displaying decorative items. Natural light filters through sheer curtains, accentuating the neutral tones on the walls and tiled floor.

4.93 out of 5 average rating, 181 reviews

The Enchantment, Cozy guesthouse,7mi to the beach!

Enjoy the beach in style! We welcome you to the private studio on the West side of Bradenton. Beautiful beaches like Cortez Beach, Coquina Beach, Holmes Beach, and Anna Maria Island may be reached in about 20 minutes. Sarasota Airport, IMG, art galleries, Lido Key, Longboat Key, museums, theaters, 2 hours from Disney World Orlando, Marie Selby Botanical Garden, and Marina Jacks are all within 20-30 minutes!

A charming outdoor patio area features a wooden pergola overhead, providing shade. Potted plants and herbs are arranged thoughtfully around the space. Two sets of double doors lead inside, complemented by white garden furniture, inviting relaxation and connection with nature.

4.98 out of 5 average rating, 281 reviews

Casita Lantana, a 1925 cottage in a Tropical Oasis

Welcome to my original 1925 Casita, built in the heyday of the John Ringling era. We are centrally located between Sarasota, Lakewood Ranch, and Bradenton, making it an ideal place to explore all the area offers. Getting around is easy since we are located very close to the Ringling Museum of Art. Plus, it is only a short 15-minute drive to downtown Lido Beach and St. Armands Circle.

A spacious bed with a soft headboard is centered against a light-colored wall. Two pillows are arranged neatly on the bed, complemented by a cozy blanket. A bedside table holds a lamp and a small plant, while wall-mounted shelves display additional greenery.

4.94 out of 5 average rating, 108 reviews

Peaceful Paradise

Kick back and relax in this calm, stylish space. Our one bedroom, one bath guesthouse has a private entrance, and separate fenced area. The neighborhood is safe and quiet. Four miles to IMG (Bradentons premier sport's school) and just 6 miles to the beautiful sandy beaches of Anna Maria Island. A perfect location for professionals, traveling singles and couples looking to get away.

Popular amenities for Bradenton guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guesthouse in Central Oak Park

A private backyard features a heated pool surrounded by lush tropical plants and trees. The pool has a gentle curve and is accompanied by stone steps leading into the water. A small seating area is partially visible in the background, set amongst vibrant greenery.

4.98 out of 5 average rating, 220 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

4.78 out of 5 average rating, 115 reviews

A sleeping area features a spacious bed adorned with multiple pillows and a decorative bolster pillow. A collection of framed artwork is displayed on the wall above. A bedside lamp and a wooden nightstand are positioned nearby, adding functionality to the space.

Guesthouse in Tampa

Sonia's Little House

A welcoming living space is visible through an opening, featuring a comfortable blue chair and a wall-mounted TV. Natural light filters through a window, illuminating the white walls and partially covering a cozy bed with blue and white bedding in the adjacent area.

4.88 out of 5 average rating, 226 reviews

Supercute Beach Themed Retreat Free Parking Wi-FI

4.96 out of 5 average rating, 190 reviews

An outdoor tiki hut porch is illuminated by soft string lights. Comfortable seating creates a cozy gathering area, surrounded by lush greenery. A wooden dining table sits in the center, offering a relaxed space for meals or conversation.

Guesthouse in Dunedin

Tiki Hut Cottage

Superhost

An outdoor seating area is sheltered by a wooden pergola adorned with string lights. A cozy couch is positioned on a decorative area rug, complemented by a small table. Lush greenery surrounds the space, providing a tranquil environment for relaxation.

Guesthouse in Dunedin

4.84 out of 5 average rating, 126 reviews

Guest House in prime location!

4.95 out of 5 average rating, 325 reviews

A charming guest house exterior is showcased, featuring a sloped roof and large glass doors. The inviting solarium area displays comfortable seating arrangements. Lush green plants are positioned beside the entrance, and the space is surrounded by well-maintained artificial grass, enhancing the outdoor atmosphere.

Guesthouse in Tampa

Tiny House Oasis Blue Vatican . Near MacDill Base

Guesthouse in Tampa Heights

A bright bedroom features a spacious bed with layered bedding, complemented by decorative pillows. Two comfortable armchairs are positioned beside a small table, and large windows provide natural light, showcasing a floral wallpaper pattern and hardwood flooring.

5 out of 5 average rating, 129 reviews

Newly Built Above-Garage Apartment near Downtown

Guesthouse in Greater Woodlawn

A spacious living and dining area showcases a large wooden dining table with four chairs. Comfortable seating consists of a brown couch and a decorative area rug. A fireplace adds charm, with natural light filtering through multiple windows.

4.95 out of 5 average rating, 256 reviews

C'est La Vie [RENOVATION COMPLETED JUNE 2020]

Guest house rentals with a patio

Guesthouse in St. Petersburg

A hot tub is surrounded by lush greenery and vibrant red flowers, creating a serene atmosphere. A tall palm plant is visible beside the tub, complementing the tropical landscape. A large umbrella is positioned nearby, providing shade on bright sunny days.

4.96 out of 5 average rating, 120 reviews

Cozy Tropical 2BR Casita + Hot Tub • Near Downtown

5 out of 5 average rating, 112 reviews

A charming guesthouse is seen from the front yard, featuring a green exterior with white trim. A welcoming porch is adorned with two chairs, and gentle landscaping with shrubs compliments the space. The surrounding grass is well-kept, enhancing the inviting presence of the home.

Guesthouse in Tampa

Stylish☀Mini Mint Bungalow☀10 mins from downtown

Guesthouse in Apollo Beach

A bright sleeping area features light wood flooring and a wooden ceiling. A spacious bed is paired with bedside tables and a small dining table for two. Wall-mounted lighting provides soft illumination, and an air conditioning unit ensures comfort.

4.96 out of 5 average rating, 113 reviews

Waterfront Studio Home in Paradise

4.86 out of 5 average rating, 114 reviews

An exterior view of a well-lit garage with a modern stone façade. The white garage doors are flanked by tall, symmetrical planters with neatly trimmed shrubs. Soft illumination from the overhead lights enhances the clean lines of the architecture, creating a welcoming entrance.

Guesthouse in Seminole

Luxury Guest House close to the beach

A white gate opens to a well-maintained outdoor area, featuring a concrete patio with lounge chairs and a small table. Lush greenery surrounds the space, contributing to a serene outdoor setting. The pink exterior of the building is visible in the background.

4.92 out of 5 average rating, 131 reviews

Have a great time

Guesthouse in Historic Kenwood

The kitchen area features granite countertops and stainless steel appliances. An oversized kitchen island with two stools offers a space for meals. A door leads to the outdoor area, while a washer and dryer are conveniently situated to one side.

4.95 out of 5 average rating, 147 reviews

Oasis historic cottage w/Tropical Patio/Parking

Guesthouse in St. Petersburg

The bright living area features a green sofa with a decorative pillow, a white coffee table, and a dining table with four chairs. Vibrant wall art enhances the space, complemented by large windows allowing natural light. A doorway leads to the private side yard.

4.98 out of 5 average rating, 144 reviews

Relaxing & Charming Hideaway

4.93 out of 5 average rating, 124 reviews

A private outdoor deck is shown with a mix of seating areas. A cozy sectional sofa is paired with square coffee tables, surrounded by decorative chairs. A large umbrella provides shade, while a tree adds a natural element to the space, creating an inviting area for relaxation.

Guesthouse in Seminole

Beachy Bohemian Bungalow with all the perks!

Guest house rentals with a washer and dryer

Guesthouse in Crescent Heights

A light-colored cottage is highlighted, featuring a welcoming red door. A paved outdoor area with a round glass table and four chairs is situated under a pergola with string lights, providing an inviting space for relaxation.

4.95 out of 5 average rating, 115 reviews

Crescent Heights Cottage

4.86 out of 5 average rating, 148 reviews

A sandy beach stretches out under a clear blue sky, featuring colorful umbrellas dotting the shoreline. Beachgoers are seen relaxing on towels and enjoying the sun. Two pool noodles lie on a striped beach mat in the foreground, contrasting with the sand.

Guesthouse in Uptown

Pool & Close to dtwn w/2 Bikes

Superhost

An outdoor patio area is enclosed by a wooden fence, featuring a fire pit surrounded by two white adirondack chairs. Lush greenery and small shrubs border the space, which is accentuated by a stone path and grassy patches under a clear blue sky.

Guesthouse in Bayshore Beautiful

4.84 out of 5 average rating, 255 reviews

La Casa Azul - Private Detached Guest House

Guesthouse in Seminole Heights

The spacious open room features a queen-sized bed with light linens, complemented by bedside tables and lamps. A small dining area with a distressed table and chairs adds charm, while natural light filters through the windows, illuminating the soft, neutral color palette.

4.97 out of 5 average rating, 204 reviews

Coastal in the Heights

Guesthouse in Historic Kenwood

The exterior of a newly built garage apartment is presented, featuring a modern design with light green siding. A single-car garage is visible, flanked by two small windows above. Natural light illuminates the gravel driveway and surrounding landscaping.

4.98 out of 5 average rating, 122 reviews

2 bedroom guesthouse in hip Grand Central District

Guesthouse in Forest Hills

A cozy sleeping area features a spacious bed adorned with neutral-toned bedding and decorative pillows. An inviting seating area with a sectional sofa is visible, accompanied by a mounted television. Natural light streams through a window, enhancing the overall ambiance of the suite.

4.94 out of 5 average rating, 284 reviews

Cozy Suite

Guesthouse in Historic Kenwood

The living area is furnished with a brown sofa and a matching loveseat, featuring colorful patterned cushions. A coffee table is centrally placed on a patterned rug. The open kitchen showcases dark cabinetry and modern appliances, with a small dining set of two tall stools at the counter.

4.98 out of 5 average rating, 123 reviews

Guesthouse in Downtown St Petersburg