Family-friendly holiday rentals in Bradenton Beach

Charming 2BD/2BR with Big Water Views on the beach

Our charming 2 BR/ 2 Bath condo has wonderful unobstructed views of Anna Maria Sound. It was totally remodeled in 2020. The property is in the Bradenton Beach area of Anna Maria Island. The Beach is right across the street with deeded access. The pool is the largest heated pool on the island. Bikes and kayaks are included. A free trolley stop is right in front of the property. There is a washer/dryer in the unit. The 2nd bedroom has both a queen bed and a bunk bed for larger parties.

Ice Cream Escape | Heated Pool+Hot Tub+Game Room

Splash into Sweet Memories! 3BR, 3BA ice cream-themed luxury escape with a heated saltwater pool, hot tub, game room & backyard oasis featuring a one of a kind custom tavern. Spacious living, vibrant decor & endless entertainment make it perfect for families and friends with plenty of fun for the little ones. Sleeps 10+ comfortably and just under 7 miles from Anna Maria Island’s world-renowned breathtaking beaches. Create your lasting sweet memories—book now for your dream Florida getaway!

Absolute Beach on Anna Maria Island

Welcome to your perfect Anna Maria Island getaway. This charming 3-bedroom, 2-bath beach retreat offers a relaxed and comfortable space just steps from everything you come to the island to enjoy. From the moment you arrive, you’ll feel right at home. Leave your car parked and enjoy the convenience of being just a short 0.1 mile stroll to the beach access—only a couple minutes on foot. The free island trolley stop is just as close, making it easy to explore all of Anna Maria Island ...

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

Playa Esmeralda Home! And add a golf cart!

Our beach home rental boasts 5 bedrooms, 5 1/2 bathrooms we Accommodate up to 12 P, hot tub, bar, play area, full kitchen, and an amazing rooftop with ocean views! Located only two blocks from the beach and just one block from restaurants and shops, this vacation rental has everything you need for a relaxing and fun getaway. Whether you're planning a family vacation, a girls' trip, or a reunion with friends, this beach house has plenty of space to accommodate everyone comfortably.

Resort Style Retreat, Pickleball, Htd Pool, Play.

- FREE POOL HEAT, private pool - PICKLEBALL COURT in our back yard. - 2 King Beds, Queen sleeper sofa, 2 bunk beds - Close to Anna Maria Island - 7.3 miles to IMG Academy - Large back yard fully fenced - BBQ Grill - Outdoor TV - Corn toss - Ping Pong - Boardgames - Outdoor dining table - 1 mile from Robinson Preserve: kayak rentals, nature hiking, running, and playgrounds - Beach chairs, beach towels, cooler, umbrella provided. - pack n play, high chair - Smart TV in every room

New! Pool + Rooftop+ 2 Min Walk to Beach & Bay!

🌊💫Welcome to Beachside Blessings—A Coastal retreat perfectly positioned between the Gulf beaches and the Intracoastal Bay—both just a 2-minute walk away! 🌅 Enjoy sunrise walks by the bay and sunset views of the Gulf, then relax in your private backyard oasis featuring a brand new heated pool and fire pit. ☀️This 3-bedroom, 3-bath beach house offers open living spaces, a rooftop lookout with outdoor areas designed for easy island living. 🏖️ Beach gear provided!

4 BR Pool Home | Sand Volleyball | Near AMI & IMG

Escape to Two Palms, a spacious 4-bedroom, 3-bath retreat in Bradenton, Florida. Perfectly located just minutes from the sugar-sand beaches of Anna Maria Island. Designed with comfort and relaxation in mind, this home offers everything you need for a memorable getaway. Step inside to an open-concept living space filled with natural light and plenty of space to unwind. Outside, enjoy a private salt-water pool and a beach sand backyard featuring a sand volleyball court.

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!

Less than a 2 min WALK to the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. Large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with bathrooms on opposite ends of the house (a pocket door adds privacy). Private heated saltwater pool sits amidst the tropical yard. Hop on the free trolley and explore Florida's gorgeous Anna Maria Island.

Casa Bella-5BR/Waterfront/Pool/Spa-9 Min AMI

Beautifully renovated 5 bedroom home. Located 3 minutes from beach access and 9 minutes to Anna Maria Island. A massive waterfront patio with string lights and heated pool and spa encompass this house. Master bedroom with walk-out to spa. Custom double walk-in shower in master suite. Family room with 86" television, decorative fireplace, and 15' ceiling. Roku TV’s in every bedroom. Outdoor propane grill. Beach chairs, umbrella, and cart. We welcome you to Casa Bella.

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.

Relaxing 3BR Retreat+ Hot Tub + Pool +Beaches +IMG

🌴Welcome to Beachway Haven! This 5-Star ⭐️ hideaway is just mins from Anna Maria Island's Pristine Beaches & the Gulf of Mexico. Dive into relaxation with your own Heated Saltwater Pool & Spa Hot Tub, nestled in a tropical oasis. Only a skip away from Golf Courses, Nature Parks, IMG Academy, & Palma Sola Causeway's Beach Access – your gateway to Horseback Riding, Kayaking, & endless sandy adventures. Shopping & dining are only a few mins away too!