Holiday rentals with a pool in 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

A serene outdoor space showcases a sparkling pool framed by lush tropical landscaping. Palms and vibrant plants surround the area, with a flamingo statue in the foreground. Soft lighting from string lights enhances the tranquil atmosphere as the sky transitions to dusk.

5 out of 5 average rating, 61 reviews

Flamingo Royale — Beach Luxury Resort

Welcome to the Flamingo Royale — Your luxury sanctuary! This exquisite escape gives tropical elegance perfect for indulgent relaxation and unforgettable memories. Experience the charm of old Florida with a modern twist in a stylish setting. Step outside to your personal paradise—a shimmering pool surrounded by lush landscaping & palms galore. W/ beautiful Anna Maria Island just moments away, relish pristine beaches, boutique shopping, and fine dining. Experience paradise at the Flamingo Royale!

5 out of 5 average rating, 65 reviews

Pool & Sports Court | Near Anna Maria + Beaches

Welcome to Sunny Oasis, a luxurious vacation home with easy access to Bradenton’s local attractions, including beautiful beaches. The incredible property features a heated pool and is the only one in the area with a private pickleball/basketball court. Other modern amenities and decor make this the perfect place for your next vacation. Bradenton Beach - 10 Min Drive Riverwalk - 10 Min Drive Anna Maria Island - 10 Min Drive IMG Academy - 10 Min Drive Sarasota - 20 Min Drive Learn More Below!

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.

Guest house 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

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, 117 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!

4.94 out of 5 average rating, 120 reviews

Home in Holmes Beach

The Peachy Beach House, steps to the gulf

The perfect place for a combination family vacation and some romance-when the kids are in bed, turn on the spa and music. June, July and August, Saturday to Saturday only. If custom trip length is wanted- ask Two bedroom, 2 full bathroom, new heated private pool/spa Steps to semi-private gulf beach, on quiet street in N. HB Well-stocked kitchen, 2 TVs, large primary suite and amazing gulf views from bedrooms. Crib, high chair, beach chairs, wagon, umbrella, beach toys and towels

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

Relax with the family at this tropical oasis. Sunrise Villa sits in the corner of a quiet cul-de-sac, just a quarter mile from Palma Sola Bay and 5 miles from the quaint island of Anna Maria and its sandy white beaches. Enjoy the tropical backyard paradise and the abundance of restaurants, beaches, and entertainment in close proximity. Lounge by the pool, take a bike ride along the bay, take a short bike/car ride over to the island, or take a short car ride to downtown Bradenton.

4.97 out of 5 average rating, 157 reviews

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

We sleep 18 AND 2 baby crib MESSAGE ME FOR ADDITIONAL INFO 5 BEDROOMS!!! NEW PICKLEBALL COURT- new mini golf course- Kids playground- Hot tub- bunks with tube slide- Arcade room- pool table and more! ▪️2 Game Rooms ▪️2KingSuites ▪️7 miles to Beach ▪️Blackout curtains ▪️BabyMonitor▪️Crib AND Pack N Play ▪️HighChair ▪️beach chairs▪️pool table▪️hot tub ▪️pickleball▪️RokuTV’s▪️Self Checkin ▪️AirHockey ▪️Grill ▪️FirePit ▪️Washer/Dryer ▪️Coffee Bar▪️Cable ⭐️No Checkout List⭐️

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.

4.95 out of 5 average rating, 126 reviews

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.

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

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.

An aerial view captures a heated saltwater pool accompanied by a spa hot tub, surrounded by a stone patio and tropical landscaping. Loungers and Adirondack chairs are positioned for relaxation under a shaded umbrella. A serene pond and lush greenery create a tranquil backdrop.

5 out of 5 average rating, 118 reviews

Relaxing 3BR Retreat+ Hot Tub + Pool +Beaches +IMG

🌴Welcome to Beachway Haven! This 5-Star ⭐️ hideaway is just mins from Anna Maria Island's Pristine Beaches & the Gulf of Mexico. Dive into relaxation with your own Heated Saltwater Pool & Spa Hot Tub, nestled in a tropical oasis. Only a skip away from Golf Courses, Nature Parks, IMG Academy, & Palma Sola Causeway's Beach Access – your gateway to Horseback Riding, Kayaking, & endless sandy adventures. Shopping & dining are only a few mins away too!

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.

4.95 out of 5 average rating, 185 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.

Popular amenities for Bradenton rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A vibrant outdoor space is showcased with a table and chairs under a large umbrella, surrounded by lush greenery. The game room features a pool table and retro arcade games, while cozy seating areas inside invite relaxation. A glimpse of the heated pool is visible in the courtyard.

4.93 out of 5 average rating, 44 reviews

Super Clean, Heated Pool & Hot Tub, 6mi to beach

A spacious screened lanai is shown with comfortable seating arrangements, including a blue lounge chair and dark woven furniture. The heated pool is visible beyond the seating area, surrounded by lush greenery, while a ceiling fan offers a cooling breeze.

4.99 out of 5 average rating, 69 reviews

Beach Vibes Vacation Home w/ Heated Pool

4.97 out of 5 average rating, 114 reviews

A bright living room features a large, light-colored couch adorned with patterned cushions. A swing chair hangs in the corner, and a coffee table sits in front of the couch. Soft lighting and large windows enhance the cozy atmosphere.

Home in Sarasota

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

Superhost

An inviting outdoor space features a spacious pool surrounded by a screened lanai. Comfortable seating areas are visible, with vibrant cushions and a backdrop of large glass doors leading into the house. Soft evening light creates a warm atmosphere, enhancing the tranquil setting.

4.86 out of 5 average rating, 50 reviews

Large 3BR Home, Heated Pool! Close to Beach, IMG

5 out of 5 average rating, 38 reviews

A private heated pool is surrounded by a spacious patio with lounge chairs and an umbrella for shade. The modern two-story home features large glass doors that brighten the living spaces, and vibrant greenery enhances the outdoor area.

Home in Arlington Park

Sarasota Escape | Minutes to Beaches + Downtown

4.94 out of 5 average rating, 136 reviews

Home in Apollo Beach

Waterfront Pool Oasis •Kayak, Games & Sunset Views

Superhost

A spacious outdoor area features a sparkling pool surrounded by concrete and decorative grass. A hot tub is integrated into the pool's design. Adjacent structures include an outdoor grill/bar area, offering a perfect space for relaxation and entertainment under clear blue skies.

4.8 out of 5 average rating, 85 reviews

3BR/2BA Private Oasis: Pool, Hot Tub, Dining

An aerial view showcases a spacious backyard featuring an expansive swimming pool bordered by vibrant orange umbrellas. The pool area is complemented by a soothing hot tub, a mini-golf course, and a landscaped patio with seating. Lush greenery surrounds the space, enhancing the tropical ambiance.

4.88 out of 5 average rating, 32 reviews

Villa Tessa, 4BR, 3BA, 12 PPL, Pool/Spa, Mini Golf

Apartment rentals with a pool

4.97 out of 5 average rating, 353 reviews

A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.

Apartment in Siesta Key

On the Beach; Siesta Key SunBum Studio

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

Apartment in Bradenton Beach

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, 159 reviews

Beach Escape & Pool, steps to Beach & restaurants

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

Apartment in Holmes Beach

4.96 out of 5 average rating, 101 reviews

Steps to the beach! Condo with pool at The Terrace

Apartment in Longboat Key

4.98 out of 5 average rating, 220 reviews

Oceanfront: Open Su - Th, $216/nt + Fees!

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

Apartment in Treasure Island

An open-concept living area features a light-colored, patterned sofa paired with a wooden coffee table. A large flat-screen TV is mounted on the wall, and a serene window nook offers natural light, enhancing the coastal charm of the space.

4.96 out of 5 average rating, 191 reviews

~Shore Thing~ Coastal Exquisite Waterfront Condo

Other holiday rentals with a pool

4.9 out of 5 average rating, 10 reviews

A private pool is enclosed by a safety fence and framed by lush tropical landscaping. Colorful pool floats rest on the surface of the clear water, while a wooden deck leads to the pool area, creating an inviting outdoor space for relaxation.

Home in Palmetto

Designer 2BR Retreat w/ Private *Heated* Pool!

A serene backyard scene showcases a saltwater pool with a calming waterfall cascading over smooth rocks. Lush tropical plants and palm trees create a vibrant, green backdrop, enhancing the natural beauty of the private oasis.

4.97 out of 5 average rating, 30 reviews

Waterfall | Spa | Saltwater Pool | Private Oasis

An outdoor dining area is set up with colorful tableware and a pineapple centerpiece. A spacious table with seating for eight is positioned near the saltwater pool, surrounded by lounge chairs and umbrellas. A vibrant playhouse adds a whimsical touch to the lush backyard.

4.96 out of 5 average rating, 25 reviews

Poppi Beach House: Heated Pool~Mini Golf~Game Room

Superhost

A modern cottage is shown with a welcoming front porch featuring white railings. Two teal chairs are placed on the porch, surrounded by palm trees. Soft sunlight is seen illuminating the exterior, highlighting the light-colored siding and clean lines of the structure.

4.85 out of 5 average rating, 20 reviews

Cozy, modern cottage near beach!

An engaging game room is featured with arcade consoles, inviting vibrant decor. The outdoor area displays a colorful swimming pool surrounded by lounge chairs and an umbrella. A putting green is visible alongside the pool. A bird's-eye view captures the lively pickleball court in bright hues.

5 out of 5 average rating, 22 reviews

Pickleball, Heated Pool & Spa, Golf, 5 mi to AMI

5 out of 5 average rating, 41 reviews

A sparkling blue pool is surrounded by a stone deck and lush greenery. Lounge chairs are positioned beside the pool, with a covered patio in the background. The water canal and boats are visible beyond the backyard, under clear blue skies.

Home in Cove

Canal front, dock, heated Pool, near AMI+IMG

An aerial view showcases a welcoming single-story home with a landscaped front yard and driveway. The home is set against a tranquil backdrop of trees and waterways, reflecting a serene atmosphere.

4.92 out of 5 average rating, 25 reviews

*Lakefront Oasis | Heated Pool | AMI | Sleeps 10