Guesthouse holiday rentals in Bradenton

A heated swimming pool, shaped organically, is nestled within a screened enclosure, providing a serene escape. Surrounding planters filled with vibrant flowers add color to the outdoor space, while comfortable lounge seating creates an inviting area for relaxation.

4.94 out of 5 average rating, 126 reviews

Near Anna Maria Island Beach-Studio on Wares Creek

This place delivers ample living space,latest amenities, and quick,easy access to Coastal Water,Anna Maria Island Beaches,and city Down Town. Spacious,bright,and tastefully furnished,with great screened porch,cozy gazebo,sparkling heated swimming pool . We supply 2 kayaks and everything that you might need to spend a day at the beach or on the water.We also supply fishing rods(adults and kids) and bait bucket. We can take you on a coastal trip in our boat if you wish (extra charges will apply )

ValueFamilyKitchen

A cozy living area features a light blue wall, with a comfortable white sofa arranged around a neutral-toned rug. In the foreground, a wooden dining table with four chairs provides seating. Natural light enters through a doorway that leads to an outdoor space.

4.98 out of 5 average rating, 103 reviews

Serenity Lake

Keep it simple at this peaceful and centrally-located place. 15 minutes from beaches this lovely apartment sits on a pond full of fish with a dock. Large pool ready for swimming and sunning. Charcoal and gas grill available. Beautiful upper deck to sit and enjoy the large mango tree and view over the lake. Golf cart available for evening rides. There is a large driveway for a boat. Swim and fishing accessories available. Minutes from I-75 - also near the famous Lakewood Ranch downtown.

FamilyLocationPets

4.95 out of 5 average rating, 347 reviews

Siesta Breeze, adorable New Beach Style Studio !

Stay at our renovated beautiful beach styled studio furnishing with a queen size bed as well as a full pull out couch bed. There’s a mini fridge, a two burner electric cooktop, a microwave, a toaster, a tea pot with complementary tea bags, coffee pot with complementary coffee and keurig with complementary Starbucks k cups. Free wifi and a 50 inch tv facing the bed. 2 minutes away from the air port, 10 minutes away from IMG Academy , 30 minutes from Anna Maria Island and siesta key .

LocationValueCondition

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, 509 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 king 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

LocationValueRiver

The living area features a comfortable seating arrangement with a light-colored sofa and two armchairs, adorned with decorative pillows. A stone fireplace is centered against a wall, complemented by wood beams overhead. Natural light filters through sheer curtains, creating a cozy ambiance.

4.99 out of 5 average rating, 138 reviews

The Cottage (In the Country) Cozy, Quiet Retreat

Relax, unwind and unplug at this cozy Old Florida-style country cottage! Here you are away from it all in peaceful bliss... but if you want to go out for dinner, it's an easy drive into town! Located on a beautiful 5 acre plot, this guest home is the perfect spot for your Florida getaway! Just 30 minutes from Siesta Key and 6 minutes from the entrance to Myakka State Park, you can see the best of Florida, both the swamps and the beaches, all in one day!

ValueFamilyComfort

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.

5.0 out of 5 average rating, 241 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.

ValueFamilyBathroom

A comfortable sleeping area is featured, showcasing a queen-sized bed with light beige striped bedding. Two bedside tables with lamps are positioned on either side of the bed. A wall-mounted television is visible, and a door leads to the bathroom area.

4.96 out of 5 average rating, 115 reviews

Modern-Fully Equipped Near Beaches, Downtown & IMG

Vacation in comfort with this Modern Farmhouse. Complimentary private parking spot, private fenced patio and outdoor seating. Fully equipped guesthouse with fridge, ductless AC, comfortable queen sized bed, high speed wifi and smart TV. Complete kitchen with stove, microwave, coffee maker and cooking utensils. Located in a quiet and established neighborhood. Minutes away from Beaches, Anna Maria Island, Bradenton Downtown, IMG, LECOM and SRQ Airport.

LocationValueSleep quality

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, 159 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!

FamilyValueBackyard

4.9 out of 5 average rating, 163 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.

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Guesthouse in South Bradenton

4.92 out of 5 average rating, 208 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!

FamilyValueCleanliness

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, 302 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 has to offer. 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.

LocationValueTV

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, 181 reviews

Peaceful Paradise Guesthouse

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.

FamilyValueBeach

Popular amenities for Bradenton guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

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, 317 reviews

Magical Guesthouse 1 mi from SRQ airport

LocationFamilyQuiet

Guesthouse in South Sarasota

A spacious sleeping area features a comfortable bed with white bedding, accompanied by a leather couch. A mounted television is positioned on the wall, and decorative plants add a touch of nature. A side table with a lamp complements the warm decor.

4.94 out of 5 average rating, 106 reviews

The Getaway

ValueFamilyCheck-in

A serene outdoor area features a pool with a curved shape, surrounded by a gated enclosure. Lush greenery and tall trees provide shade, while a light-colored building with a metal roof stands nearby. The setting offers a tranquil atmosphere for relaxation.

4.93 out of 5 average rating, 101 reviews

Amazing Location West of the Trail

ValueLocationCleanliness

A spacious room features a king size bed with coordinating pillows and light bedding. A chic chandelier hangs from the ceiling, illuminating the space. Natural light enters through the window, while a comfortable seating area with decorative pillows and a coffee table complete the inviting environment.

4.86 out of 5 average rating, 427 reviews

The Cottage, very close to Siesta Beach!

LocationFamilyTV

Superhost

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.

4.88 out of 5 average rating, 166 reviews

Perfect Florida location: Craftsman Carriage House

LocationFamilyTV

4.85 out of 5 average rating, 143 reviews

Private Guesthouse in St. Pete w/ Pool & Jacuzzi

ValueFamilyBackyard

4.96 out of 5 average rating, 142 reviews

An inviting view into the living area is framed by a decorative arch. A vibrant green plant adds a touch of nature, while a cozy brown couch and accent chairs are arranged around a circular coffee table. Colorful artwork decorates the walls.

Guesthouse in Gulfport

Gulf Guesthouse - king bed, 3 blocks to downtown.

LocationValueBarbecue

Guesthouse in Sarasota Springs

A well-appointed bedroom features a spacious bed with decorative pillows. Soft natural light filters through the window, which is adorned with brown and beige curtains. A vintage mirror adds an elegant touch, while a bedside table with a lamp provides functional lighting.

4.92 out of 5 average rating, 224 reviews

Cozy Guesthouse in central Sarasota!

ValueFamilyCleanliness

Guesthouses with a patio

4.95 out of 5 average rating, 166 reviews

Downtown Garden Studio close to everything

ValueLocationSleep quality

Guesthouse in Historic Kenwood

A warm living room is presented, featuring a light-colored sectional sofa and a dark blue armchair. A coffee table is centered on an area rug, adorned with decor. Two large windows allow natural light to fill the space, complemented by framed artwork on the wall.

4.99 out of 5 average rating, 119 reviews

Kenwood Retreat - 1BR carriage house

ValueFamilyAmenities

A charming yellow cottage is framed by lush palm trees and tropical plants, featuring a welcoming front door at the end of a paved walkway. Sunlight filters through the greenery, creating a bright and inviting atmosphere near the entrance.

4.91 out of 5 average rating, 182 reviews

St Pete Casita Studio with Salt Water Pool & Yard

ValueFamilyTV

Superhost

A bright kitchen area features white cabinetry and modern appliances, including a washer and dryer. A central table with four chairs is set for dining. A textured rug lies under the table, and a ceiling fan provides air circulation. Natural light filters through a nearby window.

4.84 out of 5 average rating, 167 reviews

Adorabe 1-bedroom effeciency with free parking

ValueLocationAir conditioning

A well-designed fire pit area is surrounded by vibrant landscaping, featuring five blue adirondack chairs positioned around a stone circle. Lush palm trees provide a tropical ambiance, and a gravel path leads to the space, inviting relaxation in the private backyard.

4.85 out of 5 average rating, 429 reviews

NEW Luxury Casita w/Hot Tub, Fire Pit, Backyard🏝☀️🏖

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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.

4.95 out of 5 average rating, 131 reviews

Waterfront Studio Home in Paradise

LocationFamilyParking

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.

4.93 out of 5 average rating, 177 reviews

Oasis historic cottage w/Tropical Patio/Parking

ValueLocationCondition

A modern living space is presented with light-colored tile flooring and large glass doors providing access to the pool area. Soft blue curtains frame the doors, while a grey sofa and sleek entertainment unit add to the contemporary design. A ceiling fan circulates air in the room.

4.99 out of 5 average rating, 158 reviews

Villa Splash, 1 room pool suite

LocationValueBathroom

Guest house rentals with a washing machine and dryer

An outdoor common area features a decorative umbrella over a bistro table, surrounded by potted plants. A wooden deck leads to a staircase, with warm lights illuminating the setting. A grill is positioned nearby, creating an inviting outdoor space for relaxation.

4.97 out of 5 average rating, 526 reviews

Coolest Downtown Neighborhood - Ebikes, Beach Gear

LocationValueParks

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.

4.94 out of 5 average rating, 209 reviews

1920s Cottage in a Private Tropical Wooded Setting

FamilyLocationBathroom

4.99 out of 5 average rating, 367 reviews

The interior of the cottage features wooden walls and a spacious layout. A comfy sofa is positioned next to a well-equipped mini kitchen, which includes cabinets and countertop space. Large windows allow natural light to fill the space, complementing the warm wood tones.

Guesthouse in Osprey

Cozy Cottage by the Bay

FamilyValueAir conditioning

Guesthouse in Historic Kenwood

4.97 out of 5 average rating, 381 reviews

Charming apartment in Historic Kenwood

LocationFamilyTV

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.

4.94 out of 5 average rating, 276 reviews

C'est La Vie [RENOVATION COMPLETED JUNE 2020]

ValueFamilyCleanliness

Guesthouse in Historic Old Northeast

A light-filled living area features a comfortable beige sofa adorned with patterned throw pillows. In the background, two bikes are parked beside a well-equipped kitchenette with navy cabinetry and a wine fridge. Sunlight streams through an open door, illuminating the space.

4.9 out of 5 average rating, 347 reviews

Beautiful Guest House in Historic Old Northeast

FamilyValueLong stay

4.96 out of 5 average rating, 238 reviews

A modern kitchen space features a marble countertop with two bar stools. Colorful wall art adorns the light-colored walls. Pendant lights hang above, casting a warm glow over the dining setup with turquoise dishes and a fruit bowl in view.

Guesthouse in Seminole

Quiet & Cozy Guesthouse minutes to the beach.

FamilyValueHiking

A cozy living area features a beige sofa adorned with bright orange pillows, inviting relaxation. A white coffee table sits in front, while a wall shelf displays decorative items. Natural light filters through two windows, brightening the space. A door leads to the outside.