Holiday rentals with a pool in West 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, 117 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.

4.96 out of 5 average rating, 113 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!

4.94 out of 5 average rating, 139 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.

4.96 out of 5 average rating, 114 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!

4.78 out of 5 average rating, 267 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. Pool heating available. 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 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, 104 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.

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, 122 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 game room is showcased, featuring a pool table as the focal point. A comfortable seating area with two sofas is arranged nearby, and a large wall-mounted TV is visible. Ambient lighting from a modern chandelier enhances the space, while a decorative neon sign adds character.

4.97 out of 5 average rating, 114 reviews

Luxe Escape: Fire Pit, Pool, Golf near AMI & IMG

Searching for the ultimate family beach getaway? 🌊☀️ Look no further than Riverview Retreat — your dream summer escape! 🏠 5 Bedrooms | 3.5 Bathrooms | Sleeps 18 💦 Heated Pool + Outdoor Lounge 🏖️ Just Minutes from Sandy Beaches 🍽️ Gourmet Grilling & Alfresco Dining 🎯 Indoor/Outdoor Games for All Ages 🐾 Pet-Friendly — Bring the whole family! Pack your swimsuits, bring your loved ones, and get ready for endless sunshine, fun, and memories at Riverview Retreat!

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, 392 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.

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, 191 reviews

Luxury 3/3 Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features one of the best unobstructed water views of Anna Maria Sound and Tampa Bay in the community. The unit features a gourmet kitchen, high-end mattresses, furniture and electronics. The unit comes with bikes and plenty of beach gear. Come enjoy one of the best units in the only luxury development in the area. Skip the hassle of a trip to the off-site management office with keyless entry.

A sunny backyard features a refreshing saltwater pool surrounded by a smooth deck. Blue and white lounge chairs create a comfortable lounging area, while a vibrant yellow bungalow is seen in the background. Lush green turf offers a spacious setting for relaxation.

4.94 out of 5 average rating, 199 reviews

Private Heated Pool, Turfed Putting Green Retreat

Imagine life in a tropical oasis-surrounded by palms trees, turfed lawn and putting green while enjoying the Florida sun relaxing your private saltwater heated pool with extended sun shelf. This 3 bedroom/2 bath 1940s bungalow is a great place to relax and unwind with your own resort style backyard. The fully equipped home, located between downtown Bradenton and Anna Maria Island offers fun in every direction. We guarantee you'll want to stay awhile!

An aerial view captures a serene private pool encompassed by a stone patio, with several lounge chairs arranged nearby. Lush greenery and tropical plants border the scene, while a dark pond reflects the surrounding nature, enhancing a tranquil outdoor space.

5 out of 5 average rating, 116 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!

Popular amenities for West Bradenton rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A refreshing outdoor pool is set against a backdrop of lush greenery. The pool features a clear blue water surface and a smooth, tiled edge. Two ladders lead into the water, offering easy access for swimming and relaxation.

4.92 out of 5 average rating, 79 reviews

IMG Academy-Modern Home Heated Pool Beaches 8 min

A private saltwater pool is framed by swaying palm trees and a sun shelf. Two lounge chairs are positioned nearby for relaxation. The surrounding space is brightened by natural sunlight, with a white fence and lush greenery enhancing the serene atmosphere.

5 out of 5 average rating, 47 reviews

Modern 3BR Retreat + Anna Maria Beaches + IMG!

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.

5 out of 5 average rating, 61 reviews

NO FEES | Heated Pool | Game Room | Sleeps14 | BBQ

A screened-in pool area showcases a sparkling blue pool surrounded by tropical landscaping. Two lounge chairs provide a relaxing spot, while a shaded patio area allows for comfortable outdoor seating. The space is enclosed for tranquility and pest control.

4.9 out of 5 average rating, 29 reviews

Palm Breeze Heated Pool Home

The grotto pool area showcases a natural stone waterfall cascading over rugged rocks into the clear blue water. Lush tropical greenery surrounds the pool, creating a serene retreat atmosphere, while two teal lounge chairs are positioned nearby for relaxation.

5 out of 5 average rating, 30 reviews

Grotto Pool Retreat | 3BR Home Near IMG & Beaches

4.96 out of 5 average rating, 26 reviews

King Bed/Pool/Game Room/Fire Pit/Hammock/Near AMI

The exterior of the property features a modern single-story home with a grey garage door. A lush green landscape surrounds the entrance, highlighted by a flowering bush. A paved driveway leads to the front door, complemented by palm trees and well-maintained shrubs.

4.93 out of 5 average rating, 30 reviews

Sleeps 11, Pool, Close to Anna Maria Beaches

A spacious backyard features a private heated pool surrounded by cushioned loungers and vibrant umbrellas. An artificial green for putt-putt adds to the outdoor entertainment along with a cozy dining area. Lush tropical plants enhance the resort-like ambiance.

4.78 out of 5 average rating, 51 reviews

Resort Yard! Mini Golf ~ Heated Pool~Fire Pit

Condo rentals with a pool

4.88 out of 5 average rating, 120 reviews

A living room area features large sliding glass doors that open to a private balcony with views of the Gulf of Mexico. Soft gray furniture is arranged around a coffee table, and a flat-screen TV is located on a media console. Natural light fills the space.

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, 138 reviews

Cozy 2 bed/2.5 bath townhome

4.99 out of 5 average rating, 204 reviews

An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.

Condo in Treasure Island

Spectacular beach to bay views from this resort.

4.96 out of 5 average rating, 101 reviews

Condo in Holmes Beach

Steps to the beach! Updated Condo at The Terrace

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

4.95 out of 5 average rating, 146 reviews

Condo in Sunset Beach

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

4.99 out of 5 average rating, 163 reviews

Condo in Longboat Key

One-Bedroom Condo on LBK: Open Sat & Sun, $199/nt!

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, 183 reviews

The Seashell Cottage with peaceful water views!

Other holiday 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, 100 reviews

Palms Villa: Cozy & Minutes from Anna Maria Island

A dining area features a glass-topped table surrounded by upholstered chairs, illuminated by a woven pendant light. Natural light streams through large windows, creating a bright and inviting ambiance.

5 out of 5 average rating, 34 reviews

“Salty Sugaree" Condo-Close to AMI, IMG, & beaches

A private pool area is enclosed with a screen, featuring a clear blue pool and two reclining lounge chairs. Lush greenery surrounds the space, and a serene water view is visible in the background, enhancing the peaceful atmosphere.

4.72 out of 5 average rating, 43 reviews

3/2 Home Heated Pool/close to Anna M. Beaches/ IMG

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.

5 out of 5 average rating, 21 reviews

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

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.

4.94 out of 5 average rating, 52 reviews

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

5 out of 5 average rating, 11 reviews

4BR Oasis w/ Heated Pool, Hot Tub, and Pickleball

A bright living area features a comfortable couch and a glass coffee table. A television is positioned on an entertainment unit. Large windows offer views of the outdoor space, framed by elegant curtains. A dining area with a small table and chairs is visible in the background.

4.9 out of 5 average rating, 88 reviews

Serene 2 Bedroom Condo in ShoreWalk Resort

A serene pool area is framed by lush greenery and a white privacy fence. Vibrant yellow umbrellas provide shade over several comfortable lounge chairs arranged around the pool. The clear blue water invites relaxation and enjoyment in a tranquil outdoor setting.