Holiday rentals with a pool in South Bradenton

A spacious living area features a large sectional sofa, offering ample seating. A contemporary chandelier hangs from the ceiling, while a light-colored coffee table sits at the center. In the background, a modern kitchen is visible, accentuated by sleek cabinetry and bright lighting.

4.96 out of 5 average rating, 114 reviews

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

An inviting outdoor lanai is shown, featuring comfortable seating with colorful cushions. A wooden coffee table holds glassware, while a heated pool glistens in the background, surrounded by lush greenery. The screened area offers a seamless connection to the tranquil outdoor environment.

5 out of 5 average rating, 109 reviews

Heated Pool-Game Room-EV-Near AMI Beaches/IMG!

Enjoy easy living in this updated tropical home! Your private screened lanai is perfect for seamless indoor/outdoor relaxing, with a heated pool and covered dining/lounge area with a 58" outdoor TV! The interior of the home is bright and open with cheerful coastal decor and plenty of room to spread out. We provide everything you need with a well-stocked kitchen, gas grill, game room, beach gear, towels, EV Charger! In a quiet neighborhood with quick access to AMI beaches IMG, parks, and trails!

A screened lanai offers a peaceful retreat with a view of the pond and trees reflecting on the water. Comfortable seating is provided, accompanied by a small table. Natural light flows in, enhancing the serene atmosphere of the space.

4.97 out of 5 average rating, 129 reviews

A&A's Paradise near IMG & Anna Maria beaches

Conveniently located just 12 minutes drive from the beaches, close to IMG Academy and all amenities, this second floor corner condo has much to offer. Its picturesque lake view, modern upgrades, and spectacular open-concept design combine to enhance your vacation experience. Facilities at Shorewalk Palms include heated swimming pools, hot tubs, tennis court, basketball court, shuffle board court, pool table, ping pong table, BBQ area and a kid's playground. All are available for your enjoyment

A comfortable living area is furnished with a gray sofa and decorative pillows. A large beanbag sits on the textured rug, while a medium-sized TV is positioned on a light-colored console. Natural light fills the space through sliding glass doors, adorned with sheer curtains.

4.95 out of 5 average rating, 122 reviews

Waterfront View Mins To AMI Beaches

Luxurious lakefront 2 bedroom, 2 bathroom condo, located just 10 minutes from Bradenton Beach & Anna Maria Island. Located in the Shorewalk Resort in West Bradenton, the condo is also just minutes from the white sandy beaches of Anna Maria Island, Siesta Key, Longboat Key, Lido Key & St. Armands Circle. Whether you’re looking for a family friendly vacation, winter getaway, IMG Academy visit, romantic retreat, or you just want to relax and enjoy the Florida sun, this place is perfect for you!

The enclosed Florida room features comfortable outdoor furniture, with colorful cushions adorning the seating. A wooden coffee table is positioned in the center, and large windows provide views of the pool area outside, allowing natural light to fill the space.

4.94 out of 5 average rating, 156 reviews

Private Heated Pool | Bradenton Vacation Home

Welcome to your private Bradenton pool oasis! . This heated pool house is well situated and well-maintained in a cul-de-sac and is central to the beach (15 minute drive to Anna Maria Island), IMG Academy, The Bradenton Country Club, famous Riverwalk, downtown and numerous restaurants and shopping options. Enjoy your own private oasis with plenty of space for your family and friends with 3 bedrooms that can sleep 8 guests and a fourth bonus room that can sleep 2 additional guests

The outdoor area features a spacious swimming pool surrounded by lush tropical plants and shaded by a screen enclosure. A hot tub is positioned beside the pool, and the bright blue water reflects the clear sky above.

4.91 out of 5 average rating, 114 reviews

Exquisite modern home with pool - 10 min to beach

A beautiful modern home 10 min to Anna Maria Island and the beach with breathtaking amenities in Bradenton Florida. This 3 bedrooms, 2 bathrooms property is appointed with exquisite finishes and furniture throughout, heating and cooling pool, hot tub, large patio with lounge chair, complimentary bicycles and beach chairs, sonos system, outdoor BBQ and much more. Additional Housekeeping can be provided at an extra cost. Please contact the Property Manager for more information.

A serene backyard features a heated pool surrounded by lounge chairs and shaded areas. Tropical plants and flowers add color, while the setting sun casts a warm glow. Umbrellas provide shade over the seating, creating a welcoming space for relaxation and outdoor enjoyment.

4.97 out of 5 average rating, 113 reviews

Orange Oasis: Clean, heated pool, near beaches.

Enjoy your little slice of paradise at the beautifully decorated Orange Oasis! 3 bedrooms & 2 baths, plus a daybed with trundle. Heated Pool. High speed wifi & 4 TV's all with Hulu, Apple TV, Disney+, & ESPN. Vaulted ceiling, rainfall walk-in shower, washer & dryer, large fenced backyard, pool, garage parking, Weber grill, & a quiet safe neighborhood. The home comes fully stocked with Ziploc bags, cooking/kitchen essentials, coffee, beach essentials, & outdoor/indoor games.

4.96 out of 5 average rating, 132 reviews

A mobile home with a welcoming front porch is surrounded by lush greenery and colorful flowering plants. The structure features a light exterior, complemented by a decorative element above the porch. A carport for vehicle parking is visible, alongside a well-maintained pathway.

Cottage in Bradenton

Coastal Style 2BR cottage near Anna Maria Island

Relax with the whole family at this peaceful place to stay. Located in a mobile home/RV park 6.5 miles from Anna Maria Island, which offers some of the most beautiful beaches on the gulf coast. Centrally located between St. Petersburg and Siesta Key. This kid friendly community offers many amenities such as Pickle ball, swimming pool, shuffle board, horseshoes and gym on site. Stay a few days or a few months! Snow birds are welcome! Only 3.3 miles to Sarasota Airport.

A clear, inviting saltwater pool is surrounded by lush tropical palms. A large deck area offers seating with an umbrella, while a colorful inflatable floats on the water's surface, adding a playful touch to the serene outdoor space.

4.98 out of 5 average rating, 206 reviews

Sunshine Oasis with heated saltwater pool

3 bedroom 2 bath home just minutes from beautiful Anna Maria Island. Just 15 minutes from Sarasota airport and 5 minutes from IMG Academy. Very close to Robinson Preserve The house has WIFI and cable TV. Security camera monitors driveway. Fully stocked kitchen: Pots, pans, utensils, new stainless steel appliances, coffee maker, Keurig, etc.). saltwater pool and privacy fenced in back yard. Beach equipment provided Two stall garage for parking.

A cozy lanai features a view of the tranquil lake, with vibrant turquoise chairs arranged around a patterned rug. Potted plants add greenery, while large glass doors provide natural light and an outdoor connection.

4.96 out of 5 average rating, 203 reviews

The Seashell Cottage with peaceful water views!

Hello and welcome to my beautiful Seashell Cottage! I have completely renovated and remodeled this townhome for you! It has a new kitchen and bathroom, new vinyl plank flooring upstairs, new furniture and bedding throughout, and is freshly painted. Decorated in a turquoise beachy decor, it gives you a sense of peace and tranquility the moment you step inside! There are gorgeous water views of the lake from both the first and second floor.

4.97 out of 5 average rating, 120 reviews

[Kids Favourite] Family Fun Oasis | Heated Pool, H

Welcome to your family-friendly getaway! Enjoy a heated pool*, hot tub, swing set, sand box, fire table, BBQ, and fun arcade games for all ages. Relax in cozy king beds and kid-friendly bedrooms designed for easy stays. Located just minutes from the zoo, beaches, and great restaurants, there’s always something to explore. Whether you’re relaxing at home or out adventuring, this is the perfect place to make lasting family memories.

4.98 out of 5 average rating, 137 reviews

A spacious living room features a large grey sectional sofa with teal accent pillows, a wooden coffee table, and a light blue area rug. Large glass doors provide access to an outdoor area, while a vibrant seascape painting adorns the wall.

Apartment in Bradenton

Sweet Retreat at Shorewalk!

Bring the whole family to this great place with lots of room for fun. A spacious 2 bedroom, 2 bathroom condo on the second floor, newly renovated and fully equipped, is within walking distance of supermarkets, restaurants, the cinema, and bowling. Whether you are a single family on vacation, a couple enjoying a weekend getaway, or a sports team in training, we have you covered. Stay with us and enjoy all the comforts of home!

Popular amenities for South Bradenton rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 23 reviews

The Ultimate Escape-Swim Spa Home - Bradenton, FL

A bright and spacious retreat features a heated pool within a screened enclosure, allowing for outdoor enjoyment. The living area showcases modern decor with ample natural light. The kitchen offers sleek cabinets and countertops, while a cozy sleeping area presents a well-dressed spacious bed for comfort.

4.94 out of 5 average rating, 63 reviews

Pets Are Welcome/ Heated Pool/ Close to AMI

The living room showcases a light-colored carpet, a gray sofa, and a television on a white shelving unit. Two decorative wall hangings are displayed above the couch, and a side table with a lamp is positioned nearby. Sliding glass doors lead to a patio area.

4.9 out of 5 average rating, 39 reviews

Warm and cozy Florida townhome.

4.85 out of 5 average rating, 100 reviews

Pool • RV Park • Pets OK • 500 MB WiFi • IMG & AMI

5 out of 5 average rating, 4 reviews

IMG Lake & Beach Home with Pool White Sand Beaches

A spacious dining area features a dark wood table surrounded by four chairs, complemented by a neutral-toned area rug. Bright pendant lights hang above, illuminating the space. A modern kitchen with white cabinetry and stainless-steel appliances is visible in the background, alongside a cozy seating area.

4.96 out of 5 average rating, 69 reviews

3BR/Bungalow w/ Heated Saltwater Pool Near IMG/AMI

The outdoor space is highlighted by a shimmering private pool surrounded by a smooth concrete patio. Cozy lounge chairs are positioned nearby, with a hammock hanging in the shade. The tranquil house sits in the background under a colorful sunset sky.

4.93 out of 5 average rating, 44 reviews

Coastal Haven w/pool in Bradenton

A spacious backyard is showcased with a freshly renovated salt-water pool at the center. Comfortable lounge chairs are positioned near the pool, with a tiki bar visible in the background. Lush greenery and a putting green enhance the inviting outdoor space.

4.83 out of 5 average rating, 252 reviews

Backyard Oasis With Pool Tiki Bar Near IMG

Condo rentals with a pool

A bright bedroom features a spacious bed with light bedding and a wicker nightstand on either side, each topped with a lamp. A chair rests in the corner, and a large window offers views of greenery outside, bringing in ample natural light.

4.83 out of 5 average rating, 107 reviews

Palms Villa: Cozy & Minutes from Anna Maria Island

4.95 out of 5 average rating, 62 reviews

A spacious living area features a light-colored sofa with patterned cushions, complemented by a wooden coffee table. A ceiling fan hangs overhead, while natural light illuminates the room through an adjacent doorway. A dining area is visible in the background, enhancing the open layout.

Condo in South Bradenton

Shorewalk “A Little Piece of Paradise”

4.92 out of 5 average rating, 49 reviews

A spacious living area is illuminated by natural light, featuring a comfortable sofa and a sleek coffee table. A dining table with chairs complements the space, and sliding glass doors provide access to a balcony with outdoor seating.

Condo in South Bradenton

Luxury Condo, Free Wifi,Pools,Tennis, Beaches - 2

A fire table is positioned near large glass windows that frame a stunning sunset over the water. The reflection of the vibrant sunset is visible in the water, while the outdoor landscape is softly illuminated by the fading light.

4.97 out of 5 average rating, 203 reviews

Luxury 3/3 Margaritaville Resort

4.86 out of 5 average rating, 105 reviews

The exterior of the condo displays a modern design with a light color palette. Palm trees are positioned around the landscaped area, and two garages are visible, along with a walkway leading to the entrance. The sunny sky enhances the welcoming appearance of the property.

Condo in Siesta Key

Comfy Siesta Key Condo

4.88 out of 5 average rating, 132 reviews

Condo in Longboat Key

Sunset and beach view from your balcony Unit 403

The inviting living area features a brown leather sofa paired with a teal accent chair. A circular mirror is positioned above a coffee table, which holds magazines. A patterned rug sits beneath, and natural light filters through the sliding glass doors.

4.96 out of 5 average rating, 153 reviews

Cozy 2 bed/2.5 bath townhome

4.98 out of 5 average rating, 105 reviews

Condo in Madeira Beach

Beach Front Madeira Beach

Other holiday rentals with a pool

4.96 out of 5 average rating, 26 reviews

Two modern cottages are situated side by side, each featuring a covered porch with seating. Lush palm trees frame the entrance, while a paved pathway leads to the cottages. A clear sky with slight cloud cover complements the inviting outdoor setting.

Tiny home in Bradenton

Cozy, modern cottage near beach2

4.96 out of 5 average rating, 24 reviews

Tiny home in Bradenton

Bradenton Getaway

5 out of 5 average rating, 9 reviews

Condo in South Bradenton

Nautical Nest – Cozy Poolside Condo, Near

5 out of 5 average rating, 28 reviews

Boat Dock + Kayaks + Dolphins + Beaches + Hot tub!

A comfortable living room area is furnished with a spacious sofa, adorned with decorative pillows featuring coastal themes. Two lamps sit on side tables, providing soft lighting. A beach-themed artwork hangs above the sofa, complementing the serene color scheme of the space.

5 out of 5 average rating, 17 reviews

Best of 2 worlds at Shorewalk

An open living area is showcased, featuring a spacious sectional sofa and a coffee table. A large TV is mounted on the wall, with a stylish media console beneath. A dining table with chairs is visible, illuminated by natural light from the nearby windows.

4.95 out of 5 average rating, 38 reviews

The Lovely Family House

4.99 out of 5 average rating, 72 reviews

Aerial view showcases the property surrounded by lush greenery, with water views of the Manatee River. The image captures the nearby fishing pier, outdoor spaces, and proximity to the river, emphasizing the serene landscape and natural beauty of the area.

Villa in Bradenton

Tranquil Tide Villa - Waterview! 15 min to beach