Vacation rentals with a pool in Bradenton Beach

Beach Escape & Pool, steps to Beach & restaurants

One block from beautiful beach & waterfront dining. Newly renovated Villa in quaint quiet condo building close to everything on Anna Maria Island. Pickleball across the street. Pool literally out your back door. Perfect for a small family or a romantic getaway. *Min. renter age 25. Two minute walk to beach, trendy Bridge Street shops, marina, restaurants, bars, boat tours, mini golf and more. Brand new beds, furniture & appliances. Kitchen has everything you need. Beach supplies in hall closet.

Beautiful ground level with heated pool!

Escape to this cozy cottage on Holmes Beach, just a block from the beautiful shoreline! Perfect for families or couples, this inviting retreat features a comfortable living space and a fully equipped kitchen. Step outside to your private pool, perfect for cooling off after a day at the beach. Enjoy the tropical landscaping and outdoor seating area for relaxation. With the beach so close, you can easily indulge in sunbathing, swimming, and seaside strolls. Experience the charm of island living!

Bougie Bungalow at the Beach

This newly renovated, completely private, comfortable Anna Maria Island bungalow is super clean & very comfortable. It has an open, split floor plan, 2 king bedrooms, each with private baths, separate dining and Florida room & is only 3 houses from the amazing white sand beach, the bay & Pier. Only 1 block over is Historic Bridge Street with cool restaurants, mini golf, quaint shops & bars with live music. Once here, you never need to drive -everything is within a block walking distance!

Beachy Chic! 1st Floor Condo-Pool-Close to Beach

Enjoy this NEWLY RENOVATED FIRST FLOOR 2-bedroom 1 bath condo just a short easy 2-minute walk to the BEACH. The New Key West vibe includes a Custom White Kitchen w/ SS appl, Shiplap, luxury plank flooring, & W/D combo. The pretty modern bath was updated with custom quartz top vanity. Relax at the pool directly next door & enjoy morning coffee on the little covered patio. The 2nd bedroom can be made up as 2 twins or a King. Walk to wonderful restaurants & shops. Gas Golf Carts permitted.

TOES IN THE SAND!

Waves Edge South is one of two very unique homes situated directly on the sugar white sands of Anna Maria Island. Welcome to a dreamy island which oozes the charm of ‘old’ Florida and will remind you of yesteryear when you were young and the pace was a little slower. A place where visitors and residents are as likely to use a bicycle or a golf cart as hop in a car. An Island where the warm waters will soothe your soul and you will leave longing to return once more.

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.

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI

Enjoy Florida sun in a stunning, newly renovated 4/2 pool home! We have provided almost everything we could think of including five 4k TVs w/ Netflix and cable, wifi, heated (optional) salt water pool w/ 7' privacy fencing, adult bikes, beach gear, Pack & Play, office, board games, relaxing lounge chairs, stocked kitchen, washer & dryer, garage parking, dog crate, all in a quiet and safe neighborhood. Oh, and of course it's just 5 miles to world renowned beaches.

Luxury 3/3 Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features one of the best unobstructed water views of Anna Maria Sound and Tampa Bay in the community. The unit features a gourmet kitchen, high-end mattresses, furniture and electronics. The unit comes with bikes and plenty of beach gear. Come enjoy one of the best units in the only luxury development in the area. Skip the hassle of a trip to the off-site management office with keyless entry.

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!

Gulf Watch 204 by Duncan Real Estate

Gulf Watch #204 is a 2 bedroom/2 bath condo across from the stunning white sand beaches of Anna Maria Island! The condo has a screened balcony with views of the Gulf, a great place to enjoy your morning coffee. Living room with views of the Gulf, also has plenty of seating with large flat screen and open plan dining area with seating for 4. The kitchen is fully equipped and has an extra eat in area with a small dining table and seating for 4.

Casa Spoonbill in Bradenton, FL

Welcome to "Casa Spoonbill"—a stylish 3-bedroom, 2-bath waterfront retreat featuring a private pool (heated during winter months), canal-front dock, and direct Gulf access. Just 2 miles from the sugar-sand beaches of Anna Maria Island and minutes from kayaking the scenic waterways of Robinson Preserve—right from the house—this peaceful escape offers the perfect blend of luxury, nature, and seclusion.

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.