Holiday rentals with a pool in Bradenton

4.96 out of 5 average rating, 104 reviews

A fenced-in outdoor area features a swimming pool surrounded by a red brick patio. Sun loungers are positioned beside the pool, and a pool house is visible in the background, complemented by lush greenery and large trees draped with moss.

Cottage in Palmetto

1930s Cottage + Pool 12 miles to Beach

Located in the heart of historic Palmetto FL, you will find this adorable cottage. This home has 2 bedrooms & 1 bath in the main home with a pull out sofa, as well as, a pool house with a full bath & daybed. You will love the southern charm of this home while relaxing by the pool or having morning coffee on the front porch. There are many restaurants & shops w/in walking distance as well as local parks & preserves. If you love the beach, this home is just a short drive to FL's beautiful beaches.

4.97 out of 5 average rating, 115 reviews

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.

Condo in Bradenton

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

4.99 out of 5 average rating, 238 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, 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

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, 105 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.

4.78 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, 103 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, 121 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.

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, 115 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!

4.98 out of 5 average rating, 203 reviews

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.

Condo in Bradenton

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

Popular amenities for Bradenton rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The outdoor area showcases a heated saltwater pool surrounded by lounge chairs and a covered seating area. A manicured artificial turf putting green is prominently featured, providing a playful touch to the spacious backyard, which is framed by lush landscaping and bright skies.

4.8 out of 5 average rating, 356 reviews

Heated saltwater pool home - turf putting green

A screened-in pool area is shown, featuring a clear blue pool with sunlight reflecting off its surface. Lush greenery surrounds the space, including palm trees and other tropical plants visible through the screens.

5 out of 5 average rating, 19 reviews

Luxury Coastal Getaway, minutes from AMI!

4.77 out of 5 average rating, 111 reviews

A private pool is surrounded by a spacious patio with paver stones, offering an inviting area for relaxation. Several lounge chairs and a small table with decorative seating are positioned near the water. Lush greenery borders the yard, enhancing the secluded feel.

Home in Sarasota

Pool house by the bay

4.97 out of 5 average rating, 153 reviews

SLeePs 18- Hottub-2king suites-Pickleball-MiniGolf

An outdoor area features a heated pool surrounded by lounge chairs, a pickleball court, and a putting green, all enhanced by tropical landscaping. The interior reveals a comfortable game room with arcade games and modern amenities, providing a relaxing atmosphere for all guests.

5 out of 5 average rating, 23 reviews

Fall Special! - Family Fun - 9 min to Beach

5 out of 5 average rating, 37 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

4.93 out of 5 average rating, 86 reviews

Sea Gem | Waterfront Oasis w/ Pool, Dock + Kayaks

5 out of 5 average rating, 33 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

Condo rentals with a pool

4.97 out of 5 average rating, 132 reviews

Condo in Clearwater

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

4.94 out of 5 average rating, 154 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

4.88 out of 5 average rating, 118 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

4.85 out of 5 average rating, 130 reviews

A modern living area features a blue sofa with decorative pillows and a low coffee table. A dining set with white chairs is visible in the background. Bright natural light filters through sheer curtains, enhancing the neutral grey walls and stylish artwork.

Condo in Sarasota

Anchor house +6 min. from Siesta Beach+heated pool

4.91 out of 5 average rating, 136 reviews

A fire table is positioned in view of a vibrant sunset, reflecting shades of orange, pink, and purple across the sky. The scene is framed by large glass panels, offering unobstructed views of the horizon, enhancing the outdoor experience.

Condo in Bradenton

New Luxury 3/3 Condo in Margaritaville Resort

4.98 out of 5 average rating, 214 reviews

Condo in Longboat Key

Oceanfront on LBK!

4.95 out of 5 average rating, 144 reviews

Condo in Sunset Beach

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

4.85 out of 5 average rating, 489 reviews

A spacious balcony offers water views featuring palm trees and lounge furniture. The exterior of the building showcases a light-colored facade. A living area is furnished with a soft couch and a dining set, bathed in natural light from large windows. A pool area is visible with lounge chairs and palm trees lining the water's edge.

Condo in St. Petersburg

Waterfront condo on top floor @ Boca Ciega Resort

Other holiday rentals with a pool

4.89 out of 5 average rating, 9 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 Pool!

5 out of 5 average rating, 29 reviews

The mobile home features a covered porch with white railings, creating a welcoming entrance. Lush palm trees line the pathway, while the exterior showcases a light gray siding, under a partly cloudy sky. A concrete driveway leads up to the home.

Home in Ellenton

The Ellenton Retreat

A private backyard swimming pool is surrounded by tropical landscaping and six lounge chairs positioned for sunbathing. The pool features clear blue water, with a paved patio area and a white fence providing privacy. Palm trees and decorative plants enhance the inviting outdoor setting.

4.94 out of 5 average rating, 53 reviews

Gone Coastal - Heated pool, close to the beach

5 out of 5 average rating, 43 reviews

Beaches + Heated Salt Pool/Spa + Large Fenced Yard

5 out of 5 average rating, 4 reviews

NEW! 10 min Beaches & IMG-Pool-MiniGolf-Arcade

4.98 out of 5 average rating, 51 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

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.

4.89 out of 5 average rating, 27 reviews

Palm Breeze Heated Pool Home