Guest house holiday rentals in Bradenton

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

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!

Downtown Garden Studio close to everything

Welcome to my brand new guest house! The original building has been rebuilt and completed in December 2024 to offer a more comfortable experience for my guests. Peaceful and centrally located, ideal for relaxation and easy access to explore historic Sarasota and the beaches. A quick drive, bike or a short walk to downtown Sarasota, Selby Botanical Garden and Pineapple Street antique shops. 1.5 miles to Sarasota Bay. 3.5 miles to St Armands Circle and Lido Beach. 6.5 miles to Siesta Key.

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

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.

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.

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!

Entire Guest House near Tampa airport

Welcome to our charming guest house! Located just 12 minutes away from Tampa Airport, 20 minutes from Raymond James Stadium, and a quick 35-minute drive from Clearwater, our entire guest house offers you convenience and comfort. With a private entrance, you'll have all the privacy you need. Whether you're here for a game, a beach getaway, or to explore the city, our cozy space is your perfect home base. Book now for an unforgettable stay!

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!

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.

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.

Cozy Private Estudio • Near IMG, Beach & Airport

Cozy tropical retreat just 4.6 miles from Sarasota Airport and 7 miles from the beach. Perfect for two! Enjoy a private stock tank pool, fully equipped kitchen, comfy bed, fast Wi-Fi, and free parking. Relax in your own peaceful outdoor space and feel the tropical vibe. Ideal for a romantic escape, a beach weekend, or simply to unwind in a unique and private setting.