Holiday rentals with a pool in Bradenton

1930s Cottage + Pool 12 miles to Beach

Located in the heart of historic Palmetto FL, you will find this adorable cottage. This home has 2 bedrooms & 1 bath in the main home with a pull out sofa, as well as, a pool house with a full bath & daybed. You will love the southern charm of this home while relaxing by the pool or having morning coffee on the front porch. There are many restaurants & shops w/in walking distance as well as local parks & preserves. If you love the beach, this home is just a short drive to FL's beautiful beaches.

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

Welcome to the Paradise Fun House, the ultimate spot for your dream bash! Our Airbnb oasis is packed with tons of fun and activities for an epic stay. Cruise around on free bikes or kayaks, fish with top-notch gear, challenge friends to mini-golf, chill in the hot tub, or enjoy our game collection. Golf clubs and beach gear are ready to roll. Our spacious layout is perfect for partying all night long. Book now for the ultimate fun or relaxing experience! Boat/Dog-sitting/cleaning are available

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!

Serenity Lake

Keep it simple at this peaceful and centrally-located place. 15 minutes from beaches this lovely apartment sits on a pond full of fish with a dock. Large pool ready for swimming and sunning. Charcoal and gas grill available. Beautiful upper deck to sit and enjoy the large mango tree and view over the lake. Golf cart available for evening rides. There is a large driveway for a boat. Swim and fishing accessories available. Minutes from I-75 - also near the famous Lakewood Ranch downtown.

{The Mod Mango} Pool & Fire Pit, Near AMI Beaches

Beach days. Poolside afternoons. Evenings by the fire under the string lights. Welcome to The Mod Mango—a private, family-friendly retreat 6 minutes from Bradenton Riverwalk, 15 minutes from Anna Maria Island, and 12 minutes from IMG Academy. This spacious 3-bedroom home sleeps up to 8 and features a pool, in-pool spa, fully fenced backyard, shaded seating, propane BBQ grill, and smoker. Enjoy a fully stocked kitchen, Smart TVs, fast Wi-Fi, a dedicated workspace, and parking for a boat or RV.

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.

NEW Saltwater Pool + Spa | Mins to AMI Beaches/IMG

Spend your days playing in the pool and soaking up the sun at this coastal escape! The huge screened lanai includes a pristine heated saltwater pool with a spillover spa and sun ledge, and large covered outdoor living and dining space. The updated 3 bedroom, 2 bath interior is bright and spacious, with a lot of natural light and nearly every room flows out to the pool. Located in a quiet neighborhood with quick access to AMI beaches, IMG, walking trails, parks, shopping & restaurants!

Heated Pool Retreat Near IMG & Anna Maria Island

Private Heated Pool Retreat Near IMG + Anna Maria Island Private heated pool with water badminton 🎾, tiki bar 🍹, and fenced backyard just 2.2 miles to IMG Academy. Sleeps 6 comfortably with 2 king bedrooms, bonus queen futon, and a full-size pull-out sofa. Less than 15 minutes to Anna Maria Island beaches. 🏖️ Note: To keep the property in excellent condition, our pool is serviced on Monday's and Friday's, and lawn is serviced on Monday's. Vendors access through the side gate.

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.

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.

The Wabi House

Our home is a one-of-a-kind Wabi Sabi-inspired retreat, designed to a create a warm, peaceful atmosphere. Every space has been carefully curated with natural wood tones, custom accent walls, ambient lighting, and modern furnishings to help you truly unwind. Enjoy a private screened pool, relaxing indoor-outdoor living, and stylish spaces. Whether you’re sipping coffee by the pool in the morning. This home was designed to make your stay memorable.