Vacation rentals with a pool 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!

Private Pool + Walk 2 blocks to Beach! King Beds!

☀️Welcome to Bayberry Beach Cottage B on Anna Maria Island! Just +/- 400 feet (2 min walk) to the beach! With a Heated private pool, fenced backyard, outdoor games, & grill, it’s the perfect spot for fun-filled days and relaxing nights! 🌴This recently renovated beach cottage has 2 king bedrooms, 1.5 baths. 📍You’re just a 2-minute walk to Salt, a trendy restaurant and craft cocktail bar with live music. More local favorites and beach bars are nearby, & lively Bridge Street is only 1 mile away

Bradenton Beach 2BD - Pool, Tennis Beach Access

Enjoy laid-back island living at this beautifully updated lake-view condo, just steps from the Gulf and minutes from everything Anna Maria Island has to offer. Designed for couples or small families, this bright coastal retreat features two king bedrooms, two full bathrooms, an open living space with serene lake views, and access to fantastic community amenities. With a dedicated 5-minute beach path, community pool, tennis courts, and bocce ball, this condo offers the perfect blend of relaxation

The Florida Rooms

NEW POOL/SPA. Just 10 minutes from the beach, The Florida Rooms is a 3BR, 2BA retreat with NEW RESORT POOL & SPA, outdoor dining and living space, premium beds, rain showers, a full kitchen, and dining for 8. Extra sleeping includes a queen sofa bed and Pack ’n Play. Enjoy a pool table, ping-pong, board games, outdoor string lights, and a fire pit. We include beach gear—chairs, towels, umbrella, and wagon—for easy fun in the sun. Comfort, charm, and convenience await! Pool/spa heating included!

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!

New! 4BR Villa + Crosswalk to Sand + Beach View!

Location ‼️ Location ‼️ 🌟🌴Welcome to Starfish Villa East, this Beachside home offers a private pool, putting green, & balconies with partial Gulf views. 🏖️Unwind across from the beach and fishing pier, and blocks from Bridge Street fun! ⛱️ Beach supplies included: wagon, 8 chairs, umbrella, cooler, and towels – everything you need for a perfect beach day 💃 Walking distance to Bridge Street, where you’ll find restaurants, shopping, bars, live music, attractions, ice cream, & mini g

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 ...

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.

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.

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.