Holiday houses in Bradenton Beach

Walk to it all! Restaurants + Heated Pool +Beach!

🌊🏖️Welcome to Making Waves on Anna Maria Island-where you are steps from the beach and centrally located to it all, footsteps to the trolley stop! Escape to paradise and experience the ultimate beach getaway at this stylish beach house with heated pool, nestled in the heart of Anna Maria. Walk outside the door to the pristine beaches, renowned local restaurants, and the vibrant Bridge Street with live music, restaurants, bars, and shopping. Our beach retreat promises an unforgettable vacation!

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.

AMI Ohana Beach Resort B with fabulous salt pool!

The location with Heated Pool is perfectly situated on the island with quick access to the beach (3 minute walk from door to shore without crossing Gulf Drive), Publix grocery store, Walgreens, Manatee Public Beach, shopping, restaurants and more. The free trolley stop is steps away offering an affordable way to explore the whole island. Ohana Beach Retreat is a newly renovated triplex in Holmes Beach on Anna Maria Island. Come enjoy our heated salt water pool in an oasis of palm trees.

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 ...

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.

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!

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.

Blue Water Escape by Duncan Real Estate

The beautiful Blue Water Escape! Experience its panoramic rooftop deck views with a location in the heart of Bradenton Beach around the corner from Bridge Street! This three-story duplex begins with a walk up to the first floor above a garage stocked with beach equipment for your use during your stay. The first level features an open living area complete with a full kitchen and dining area, a balcony with a gulf view, a dual twin bedroom and a full bathroom.

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.

NEW! Sideways~Heated Pool and Spa! Steps to Beach!

🌊 Sideways is a beachside retreat perfectly set between the Gulf and the Intracoastal Waterway 🌴. Just a 1-minute walk to the beach, this home features a private heated pool & spa, rooftop deck with panoramic water views, screened porch with TV, and BBQ grill. Dog-friendly with approval, close to dining and shopping, and parking for up to four cars—Sideways offers the perfect blend of comfort, views, and island relaxation ☀️🏖️🍹

Private Beach Access • Largest Pool • Pickleball

Dan’s Florida Condos presents Sea Dream, your serene island retreat in the award-winning Runaway Bay complex. Steps from private beach access, enjoy the island’s largest heated saltwater pool, tennis/pickleball, bocce, shuffleboard, gym, and fishing pier. Relax on the screened terrace with peaceful lagoon views or stream your favorites on smart TVs—comfort, charm, and island fun all in one.

Barefoot Boho- Breezy Bungalow on the Beach!

Brand NEW Listing— recently remodeled! Chic boho style meets island comfort at Barefoot Boho. This charming bungalow sleeps 4 and has walking beach access to beautiful Coquina Beach and the Instracoastal Waterway. Relax at the tropical pool, grill fresh seafood or stroll to local restaurants. Perfect for a beachy getaway, where every detail inspires relaxation and barefoot bliss.