Family-friendly holiday rentals in Bayshore Gardens

The Lovely Family House

Your family will be close to everything when you stay at this centrally located place. Walk to IMG and SCF. Near beaches(Anna Maria,Holmes Beach,Coquina,and more). Screened in pool and patio. Plenty of places in the house to be together with others and have personal quite space too. Sleeps 11 comfortably. RV or trlr parking available. 4-5 car driveway. Grill, bikes, outdoor toys, beach gear, fooseball table, and more. 3 bedrm and 2 ba w/ sofa sleeper. Max 1 Dog. No cats. No indoor smoking

Pickleball/Heated Pool/Golf Front/Putt Green/BBall

Welcome to my 4B/2BA luxurious coastal home on a golf course, minutes to the beach, airport, downtown areas, and IMG. • 🏓 Pickleball court • 🏝️ Pool • ⛳️ Putting green • 🏌️‍♂️ Backyard on the golf course, acclaimed Sara Bay Country Club • 🏀 Professional Basketball Hoop • 🏖️ Minutes to the beach • 🌇 Minutes to downtown Sarasota and Bradenton • ✈️ <10 min to the Airport • 🎾 10min IMG • 🖼️ Serene, quite, safe neighborhood • 📶 High speed Wi-Fi • ⭐️ Top community *Whitfield Estates*

Waterfront Retreat• Private Pool• Golf• Ping Pong!

Dive into the ultimate summer getaway! Relax at this cozy waterfront cottage with a private pool, & a short drive to AMI’s white-sand beaches. 2BR/2BA with two living areas include a bright Florida room overlooking the canal. Enjoy ping pong and a putting green ⛳. Start your mornings with coffee on the dock, watching fish jump out of the water. Fast WiFi, workspace, beach gear, and a kitchen with cooking essentials. Perfect for beach days, family getaways, or a relaxing coastal escape.

Art and Design in Bradenton Villa

Art & Design at the Magic Bollettieri. The first U.S. address of The Magic Collection Retreats, this distinctive lifestyle villa marks our coastal debut beyond Europe. Nestled in sunlit Bradenton, Florida, it captures the spirit of the collection: characterful, intimate, and deeply design-led. A curated blend of Italian aesthetics and relaxed, athletic living, the villa is designed for those who move through life with purpose. Here, design meets vitality, and every detail tells a story.

Garden Home/Heated Pool/King-Bed/20 min Beach/Pets

Nestled beneath towering trees, this cozy 3-bedroom, 2-bathroom home offers a peaceful getaway. The screened-in heated pool and patio provide a quiet spot to relax and enjoy nature’s beauty in privacy. With new beds and many thoughtful amenities, it’s a comfortable retreat for your stay. Whether you're swimming, grilling, or simply enjoying the surroundings, this home offers a calm atmosphere to unwind and share time with family or friends in complete comfort. Message us with questions.

Private Heated Pool~Yacht Rental~BBQ~Near Water

You’ll instantly feel at home at Solara Oasis, a light-filled 3-bed, 2-bath Sarasota retreat with a stunning backyard paradise. Start your day lounging by the private pool, unwind by the fire pit, and enjoy spacious, stylish interiors designed for total comfort. With flexible sleeping arrangements, a fully stocked kitchen, and fun extras like board games and a smart TV, this home is your perfect getaway — just minutes from Siesta Key, Lido Beach, and downtown Sarasota.

Cozy For Two Getaway - Bradenton FL

Welcome to Cozy for Two Getaway in Bradenton! 🩷 Perfect for a couple, this small but charming space can comfortably accommodate our guests (ideally a couple and 2 small kids if pushing for 4 guests since the couch is small, but lays out). Enjoy the privacy of your own gated parking area. Located just 25-30 minutes from the beautiful Lido/Siesta Key Beach and Anna Maria Island, you can spend your days soaking up the sun and exploring the vibrant local scene here!

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.

Florida Living

This House has 3 bedrooms, 2 bathrooms, kitchen, living & dining, Pool, GAME ROOM (Pool Table, Fossball ,Bar ) 65 inchTV, wireless internet. It is conveniently located near local attractions, yet secluded and quiet. If you are looking for a private escape in a peaceful setting with comfortable furnishings and a lot of fun games this property is for you and your family .

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.

Heated Pool • Arcade • MiniGolf • Near IMG/AMI/SRQ

Unwind in this NEWLY RENOVATED spacious 4-bedroom, 2-bathroom oasis that comfortably sleeps up to 11 guests. Perfect for families, friends, or group vacations, this home offers a seamless blend of relaxation and fun with its heated pool, indoor arcade and outdoor amenities. All while minutes from IMG Academy, Bradenton and Sarasota.

*Kid Friendly w/Heated Pool* Close to Beach*

Welcome to ☀️Sarasota Sunshine☀️! This family friendly, beautifully designed property is centrally located and offers a one of a kind experience. Sleeping up to 9 guests, this luxurious space offers comfort, amenities and is close to downtown Sarasota as well as numerous beaches.