Vacation rentals with a pool in South Bradenton

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, 121 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

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, 139 reviews

Vacation Pool - House in Bradenton!

Welcome and enjoy a relaxing vacation house with your family. 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

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.

4.97 out of 5 average rating, 115 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!

4.99 out of 5 average rating, 248 reviews

A private stock tank pool is surrounded by a wooden deck and lounge chairs. An umbrella provides shade over the pool area. Colorful towels and a stylish table with refreshments are visible, set amidst a landscaped courtyard with lush greenery.

Guesthouse in Sarasota

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

4.94 out of 5 average rating, 145 reviews

A circular pool is surrounded by a landscaped area featuring vibrant plants and red stones. Lounge chairs offer seating nearby, while a shaded umbrella provides relief from the sun. Inflatable rings float in the clear water, and a view of the canal can be seen in the background.

Cottage in Bradenton

Waterfront+Pool+Putting Green+Beach Gear! 2BR/2BA

• Perfect for couples, families, or remote work escapes • Unwind by the water • Fish from dock • Well equipped kitchen (no food items) • Starter supplies: coffee, tea, paper goods & toiletries • 2 bd / 2 ba • Selfie Wall • Keyless Entry • Pool • Putting Green *Tap the 🖤 in the corner to save this listing and find it faster later* • 10 miles to beach, *Award Winning Ana Maria Island • 7 miles to IMG Academy • 11 miles to SRQ Airport • 2 miles from Pittsburgh Pirates Training Camp

A private backyard features a heated pool surrounded by a spacious patio, offering lounge chairs and a vibrant mural. The area is enclosed, providing a secure environment for families, while a putting green lies nearby, inviting guests to enjoy outdoor activities.

4.97 out of 5 average rating, 116 reviews

Heatd Pool + PuttPutt + Close2IMG + Tropical Oasis

Welcome to Turtle Cove – This freshly designed home is centrally located in Bradenton - minutes from beautiful beaches, historic downtown, and the IMG academy. This Tropical Oasis has something for the whole family, including a Heated Pool, Putting Green, Fire Pit, BBQ Grill, Pool Table, Outdoor Bar, & more! Whether you want to spend your days enjoying the beautiful beaches or soaking up rays in your private pool, you are sure to create lasting memories during your stay at Turtle Cove!

A bright living and dining area features a round glass table set for four, cozy seating arrangements with light-colored sofas, and a television. Natural light flows through large sliding glass doors, which lead to a screened lanai overlooking a serene outdoor space.

4.87 out of 5 average rating, 119 reviews

Sunny Bella Rosa – Pools, Spas, near IMG & Beaches

Welcome to Florida Bella Rosa – a charming, sun-filled lakeside condo with a warm coastal Florida vibe, lovingly decorated to make you feel right at home. Located in the sought-after Shorewalk Vacation Villas community, you’ll almost sense the gentle Anna Maria Island breeze drifting through your stay. We’re just 7 miles from the stunning Gulf/Anna Maria Island beaches and only 2 miles from IMG Academy, with Sarasota–Bradenton International Airport just a 20-minute drive away.

4.89 out of 5 average rating, 239 reviews

A welcoming living space is visible through an opening, featuring a comfortable blue chair and a wall-mounted TV. Natural light filters through a window, illuminating the white walls and partially covering a cozy bed with blue and white bedding in the adjacent area.

Guesthouse in Sarasota

Supercute Beach Themed Retreat Free Parking Wi-FI

Come and enjoy our newly remodeled 400 square foot laid back beached themed guest house. Located just 1.5 miles away from Sarasota/ Bradenton airport, and less than 10 miles away from our world famous beaches. Whether you are a single person in search of a long term stay or a family looking for a short vacation, we have the place for you. Our guest area is attached to our main residence and has a private entrance. Enjoy our shared swimming pool and outside patio areas.

4.97 out of 5 average rating, 122 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.

4.78 out of 5 average rating, 270 reviews

Tropical Oasis - Private Pool - Close Beaches

Enjoy a tropical Paradise with private pool. Beautiful palms and an over-sized private pool. This beautiful pool home is only a short drive to Anna Maria Island. Floridas most beautiful white beaches on the Gulf Coast. Huge master bedroom with attached full bath and access to the pool area. Free high speed WIFI. Smart TV in living room queen room. 2 parking spaces. Convenient to beach bars, golf, shopping. 25 Min. Sarasota and 45 Min. Tampa Airport.

A spacious living and dining area features a table set for four with light-colored chairs. A comfortable sofa is arranged against the wall, and large sliding glass doors allow natural light to flood the space, providing views of the nearby lake and greenery.

4.98 out of 5 average rating, 203 reviews

Shorewalk full condo AnnaMaria Beaches IMG

1174 sqft Shorewalk condo with 2-bedroom, 2 bath , kitchen and living room unit on desirable ground level with a beautiful lake view Within very short walking distance to grocery ,movies, shopping and dining, This condo is about 9 miles from Sarasota airport and about 13 miles from downtown Sarasota, about 6.8miles from the Bradenton Beach , about 10 miles from Anna Maria Island Less than 1 mile to the big gate of the IMG academy

4.98 out of 5 average rating, 121 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

A tranquil outdoor space features a heated pool surrounded by stone pavers. Comfortable lounge chairs are positioned nearby, and a modern fire pit offers seating. The restored stone house stands in the background, framed by palm trees under a clear blue sky.

4.96 out of 5 average rating, 23 reviews

100 yr Old Stone Home + Pool + 9 miles to beaches

4.97 out of 5 average rating, 157 reviews

SLeePs18-JaCuZi-2kingSuites-IMG-picklbal-2babyCrib

An aerial view showcases a spacious, heated swimming pool adjacent to a vibrant outdoor recreation area featuring a pickleball court and nearby children's playground equipment. The lush green lawn is neatly bordered by privacy fencing, enhancing the inviting atmosphere for recreation and relaxation.

5 out of 5 average rating, 55 reviews

Pickleball, Axe Throwing, Mini-Golf, Bowling, IMG

A serene pool is illuminated by soft lighting, surrounded by a screened enclosure. The water shimmers in gentle turquoise, highlighting the smooth curves of the pool's design. The atmosphere is calm, perfect for a relaxing evening.

4.85 out of 5 average rating, 52 reviews

Bachac Enterprise

4.94 out of 5 average rating, 120 reviews

Home in Holmes Beach

The Peachy Beach House, steps to the gulf

5 out of 5 average rating, 12 reviews

Epic Family Getaway Games Room | Hot Tub | Heated

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 out of 5 average rating, 109 reviews

Sunrise Villa - Tropical 3 bedroom home with pool

A serene outdoor space features a sparkling pool surrounded by lush greenery and tropical plants. Comfortable lounge chairs are placed along the poolside, and string lights cast a warm glow overhead. A shaded seating area with a gazebo can be seen in the background.

4.91 out of 5 average rating, 394 reviews

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

Condo rentals with a pool

Superhost

The living area features a light-colored sofa complemented by an orange accent chair. A coffee table sits on a textured area rug, while wall art adds color to the red accent wall. Glass doors open to a view of outdoors, surrounded by greenery.

Condo in Sarasota

4.9 out of 5 average rating, 133 reviews

Sunny 2nd-Floor Condo w/ Heated Pool | 1BR

Superhost

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.

4.82 out of 5 average rating, 102 reviews

Palms Villa: Cozy & Minutes from Anna Maria Island

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.

4.98 out of 5 average rating, 194 reviews

Luxury 3/3 Margaritaville Resort

4.94 out of 5 average rating, 159 reviews

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.

Condo in Bradenton Beach

Beach Escape & Pool, steps to Beach & restaurants

4.89 out of 5 average rating, 123 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, 140 reviews

Cozy 2 bed/2.5 bath townhome

4.96 out of 5 average rating, 101 reviews

Condo in Holmes Beach

Steps to the beach! Updated Condo at The Terrace

4.98 out of 5 average rating, 220 reviews

Condo in Longboat Key

Oceanfront: Open Su - Th, $225/nt + Fees!

Other vacation rentals with a pool

A living room is depicted with a light-toned sofa flanked by two gray armchairs. The glass coffee table sits atop a jute area rug. Decorative accents include two blue pillow covers and framed artwork of a wooden pathway. Task lamps are placed on side tables.

4.95 out of 5 average rating, 43 reviews

Turtle's Cove Condo!

A well-maintained pool area is surrounded by neatly arranged lounge chairs and palm trees. An umbrella offers shade by the pool, which features clear, inviting water. The exterior of a house is visible, with a surfboard displayed next to the entrance.

4.92 out of 5 average rating, 26 reviews

Jungle House (Close to IMG Academy)

A living area features a blue sectional sofa adorned with decorative pillows. A wooden coffee table sits in front, and a light-colored desk with a chair is positioned nearby. Two windows allow natural light to fill the space, complemented by tropical-themed artwork on the wall.

4.83 out of 5 average rating, 6 reviews

Coastal Retreat Cottage 1 b/1b

4.92 out of 5 average rating, 13 reviews

A balcony view is captured, showcasing a calm body of water framed by lush greenery and palm trees. A small table with a glass top holds a pot of bright red flowers, providing a vibrant contrast against the serene backdrop of the water and surrounding landscape.

Apartment in Bradenton

MM-near Beaches and IMG, Pool, Tennis, Pickleball

4.98 out of 5 average rating, 55 reviews

A screened-in pool area features a sparkling blue pool, surrounded by several lounge chairs in turquoise. Two umbrellas provide shade, while lush greenery is visible in the background, showcasing the tranquil waterway just beyond.

Guest suite in Bradenton

Waterfront Suite-20 min to Gulf Beaches

The spacious pool deck is enclosed with a screened structure, showcasing a large swimming pool with crystal-clear water. Lounge seating is present, along with a dining area featuring a table and chairs. Surrounding greenery adds to the serene outdoor environment.

4.97 out of 5 average rating, 31 reviews

Azul Oasis of Bradenton

4.91 out of 5 average rating, 35 reviews

An open-concept living area features a light wood floor with a cozy sofa in light tones. A modern dining table with black chairs sits adjacent to a fully equipped kitchen, which includes stainless steel appliances and white cabinetry. Decorative plant accents enhance the space.

Apartment in Bradenton

Modern Top Floor Unit near Anna Maria Island

A serene outdoor area features a well-maintained lawn with stone pathways and tropical landscaping. Palm trees provide shade around a bar area, overlooking the water. A private dock is visible in the background, with the gentle bayou waters reflecting the blue sky.