Holiday rentals with a pool in Bradenton Beach

An aerial view captures a heated private pool surrounded by tropical landscaping. Deck chairs and a lounge chair provide seating options, and stone pathways lead to the pool. The pool curves gracefully, inviting relaxation in a serene outdoor setting.

4.98 out of 5 average rating, 114 reviews

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!

4.96 out of 5 average rating, 112 reviews

Condo in Holmes Beach

Steps to the beach! Condo with pool at The Terrace

Just 200 steps from the white sands of Holmes Beach, this beautifully updated 2BR/2BA condo has everything to offer! Our unit features high-speed internet, Keurig , balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, bicycles, SUP, cart). This unit sleeps 6 (1-King, 1-Queen, & Full size sofa bed). LOCATION, LOCATION! You'll be just steps from restaurants, cafés, shops, and the free island trolley!

Adirondack chairs in soft blue are positioned on the sandy beach, offering scenic views of the ocean and coastline. The sun reflects off the water, enhancing the tranquil atmosphere, while a distant figure strolls along the shore. Lush greenery borders the sandy area.

4.94 out of 5 average rating, 198 reviews

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.

Townhouse in Bradenton Beach

A refreshing pool is surrounded by lounge chairs and tropical greenery, offering a relaxing outdoor space. The vibrant blue exterior of the condo stands out against the palm trees, while beach access is visible in the background, ensuring proximity to the sandy shores.

The Perfect Beach Escape: Just a 1-Minute Walk!

Immerse yourself in our Gulf Coast paradise. Second floor, 3 BR unit of two unit condo with pool shared between only the two units. The heated pool area is an oasis! Each unit has its own private outdoor seating/grill area. One car garage & 2 car spaces, ideally located 1/2 block to the white sands and azure waters of Bradenton Beach and two blocks to the Bay with access for kayaks, picnic area, playground, basketball court and two new pickleball courts. The beach sunsets are spectacular!

4.97 out of 5 average rating, 100 reviews

Bungalow in Bradenton Beach

A tranquil outdoor space features a wooden dining table surrounded by eight chairs set on a tiled patio. A small, curved swimming pool is framed by lush tropical plants, and umbrellas provide shaded areas. The vibrant greenery creates a serene atmosphere.

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!

4.91 out of 5 average rating, 128 reviews

4.96 out of 5 average rating, 51 reviews

~Hot Dates, Cool Prices – Beach Access - Lrg Pool~

🌅Breathtaking Sunsets welcome you combined with a Powder Soft Sandy Beach & Aqua Blue Water which makes AMI your memorable and desirable Vacation Destination! Your Condo is in between the Beach & the Bay! It's your ideal location for everyone including Families, Couples, Friends etc. You can Walk to Restaurants, Bars, Live Music, Shopping, Water Sports, Boating, Cruises, Fishing etc. What you'll love the most...you don't have to drive...you can Walk, Bike, or use the Free Trolley.

5.0 out of 5 average rating, 28 reviews

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

A two-story yellow condo is highlighted against a clear blue sky. Palm trees line the pathway leading to a fenced pool area. The entrance features a covered balcony with white railings, offering a welcoming view of the surrounding tropical landscape.

4.92 out of 5 average rating, 128 reviews

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.

4.79 out of 5 average rating, 34 reviews

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.

4.77 out of 5 average rating, 150 reviews

Cute 1Bedroom Beach condo, only steps from beach!

Enjoy beautiful Bradenton Beach in our newly refurnished vacation rental. We invite you to lounge by our crystal blue pool, swim in the calm gulf waters, or walk along AMI's sugar sand beaches. 2 guests are ideal in our 1 bedroom queen apartment, but we have a double height 24 inch queen air mattress to accomodate up to 4 guests. The kitchen is fully equipped and features full sized fridge, stove, oven & coffee maker. The unit has high speed wifi, smartTV, Netflix, cable, & DVD.

Townhouse in Bradenton Beach

1-Min Walk to Beach | Anna Maria Island

Welcome to your dream getaway in Bradenton Beach on Anna Maria Island! This stunning 3BR/2.5BA home is just a 2-minute walk from the beach. Enjoy a heated communal pool with a spa for relaxation. Located under a mile from Historic Bridge Street, explore shops and entertainment easily. Unwind on two balconies with breathtaking sunset views over the Gulf. The fully stocked kitchen and provided beach essentials ensure a hassle-free stay. Experience the ultimate beach vacation!

5.0 out of 5 average rating, 29 reviews

A heated saltwater pool is surrounded by lush tropical vegetation, creating a serene atmosphere. Poolside seating is offered by several lounge chairs, alongside a shaded area with an umbrella. Sunlight reflects off the water's surface, enhancing the tranquil setting.

4.98 out of 5 average rating, 205 reviews

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.

Popular amenities for Bradenton Beach rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Two bright turquoise adirondack chairs are positioned on a pebbled shoreline, facing a calm canal. Lush palm trees and greenery surround the area, while distant houses line the opposite bank under a clear blue sky.

4.96 out of 5 average rating, 129 reviews

Waterfront Pool Home Steps to Beach

4.94 out of 5 average rating, 104 reviews

Home in South Bradenton

Stylish Pool Home • Near IMG & Beaches • Top Rated

A private pool area is surrounded by palm trees and shaded by umbrellas. The inviting water reflects blue skies, while a colorful float adds a playful touch. Comfortable seating is arranged around the pool, creating a relaxed outdoor atmosphere.

4.89 out of 5 average rating, 192 reviews

Swim. Soak. Play. | Beaches | 5mi 2 IMG | Dine

5.0 out of 5 average rating, 111 reviews

Home in Anna Maria

Bean Pt. Bungalow - Half duplex w/private pool

A spacious patio is highlighted by a heated pool, surrounded by a decorative stone border. Comfortable outdoor seating is arranged nearby, beneath string lights that create a soft glow. A serene water view and lush greenery are visible in the background, enhancing the outdoor ambiance.

4.96 out of 5 average rating, 152 reviews

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

4.98 out of 5 average rating, 107 reviews

A well-maintained front yard features lush green grass and a large agave plant. The house, showcasing a contemporary design, is flanked by palm trees. A driveway leads to a two-car garage, with additional landscaped areas adding to the outdoor appeal.

Home in Cortez

Dockside Dreams - Pool, Spa & Waterfront Dock

A large heated saltwater pool is enhanced by colorful floating rings. A waterfall feature adds a calming effect while lounge chairs are positioned nearby. The patio area is visible, furnished with multiple seating options, and surrounded by lush greenery and sunny skies.

4.99 out of 5 average rating, 103 reviews

Heated Pool | Game Room | Arcade | Sleeps14 | BBQ

An inviting exterior view of Sunrise Villa showcases a well-maintained landscape featuring lush greenery and vibrant plants. A spacious driveway leads up to a garage, with decorative stone detailing accentuating the garden area. The home is framed by palm trees, contributing to the tropical ambiance.

5.0 out of 5 average rating, 134 reviews

Sunrise Villa - Tropical 3 bedroom home with pool

Condo rentals with a pool

A balcony offers a serene view of the Gulf of Mexico, featuring a lounge chair positioned for relaxation. The space is framed by a white railing, with sandy beach and greenery visible in the distance under a bright sky dotted with clouds.

4.85 out of 5 average rating, 121 reviews

Oceanfront Condo for Beach Lovers

4.98 out of 5 average rating, 258 reviews

Condo in Longboat Key

Island Time: Open Columbus Day Weekend!

4.98 out of 5 average rating, 110 reviews

Condo in Longboat Key

Beach Condo with Quiet, Private Beach

4.94 out of 5 average rating, 143 reviews

A serene outdoor pool area is surrounded by lush tropical landscaping. The well-maintained pool is framed by the charming two-story buildings of the Palm Cay complex, with lounge chairs positioned nearby for relaxation. Palm trees sway gently in the warm sunlight.

Condo in Holmes Beach

1/1 STEPS to Beach w/ Heated POOL - Sleeps 4

Superhost

5.0 out of 5 average rating, 3 reviews

Beachfront Studio on Anna Maria Island

A spacious living area is featured, showcasing a light-colored sofa and a coffee table with glass top. A television is mounted on the wall, with natural light streaming in from the sliding glass doors. A view of the screened terrace and lagoon can be seen in the background.

5.0 out of 5 average rating, 17 reviews

Largest Pool • Private Beach Access • Pickleball

A spacious heated pool is illuminated in a calming blue hue, surrounded by lounge chairs and tropical landscaping. The backdrop features the condo buildings, creating a serene ambiance for evening relaxation.

5.0 out of 5 average rating, 50 reviews

AMI Perfect Experience

4.94 out of 5 average rating, 51 reviews

2BR 250 Ft to Beach Heated Pool

Other holiday rentals with a pool

Apartment in Bradenton Beach

A cozy studio space is depicted, featuring a spacious king bed adorned with fresh linens. A comfortable sofa sits nearby, complemented by a decorative pillow. A blue side table and an upholstered ottoman add color to the room, which is illuminated by natural light through the sheer curtains.

Coconut Vacation Rentals/Studio/Steps to Beach!

4.98 out of 5 average rating, 48 reviews

4.98 out of 5 average rating, 42 reviews

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

Townhouse in Holmes Beach

A sandy beach extends towards a calm ocean, where turquoise waters meet a clear blue sky. Colorful umbrellas provide shade for beachgoers, who are relaxing on vibrant towels. The shoreline features soft white sand, inviting visitors to enjoy the peaceful environment.

Getaway Family Beach Townhome w/Pool!

4.95 out of 5 average rating, 73 reviews

Apartment in Bradenton Beach

Bayfront 2BR | Heated Pool | Walk to Beach

5.0 out of 5 average rating, 20 reviews

4.94 out of 5 average rating, 63 reviews

Beach Bungalow- 2 min walk to beach! Heated Pool

Townhouse in Bradenton Beach

Bay & Gulf Views. Waterfront+heated pool+AC

4.91 out of 5 average rating, 11 reviews

4.98 out of 5 average rating, 86 reviews

Townhouse in Bradenton

Nautic Star - Large pool & Free dock and kayaks