Holiday rentals with a pool in West Bradenton

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, 101 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 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, 68 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!

The image showcases a spacious outdoor area featuring a private pool surrounded by a screened lanai. A bright beach scene is visible beyond the pool. The garage includes game equipment, while a colorful teen shed is visible, designed for relaxation and fun.

4.89 out of 5 average rating, 96 reviews

5 stars! ⭐️🏖 HotTub&Pool-4BR/2BA 5 miles to beach!

Welcome to “5 Beaches” — the ultimate family-friendly getaway! Just minutes from five stunning sugar-sand beaches, this spacious 4BR home has everything you need for fun and relaxation. Dive into the private heated pool, unwind in the hot tub, or enjoy ping pong, air hockey, and giant Connect 4 in the game garage. With baby gear, beach gear, a fully stocked kitchen, and even a teen hangout shed, it’s perfect for multiple families. Safe, quiet neighborhood — book now and make lasting memories!

5 out of 5 average rating, 53 reviews

Heated Salt Pool & Spa+AMI Beaches+Large Backyard

The Pink Seahorse is a stunning 5 star🌟 beach house located 6 miles from the beautiful turquoise beaches of Anna Maria Island. You will find a large, fenced backyard with a sparkling heated (free) salt pool, spa and game room. We offer every amenity to make your stay unforgettable! 🏖️ Pool, Spa & Screened Lanai 🏖️ 2 King Beds & 3 Bunk Beds 🏖️ Chef's Kitchen 🏖️ Ping Ping/Pool Table & Foosball & Arcade 🏖️ 2 Grills (Gas & Charcoal) 🏖️ Game Room 🏖️ Large Yard 🏖️ Fire Pit & 8 Chairs

A private pool area is surrounded by palm trees and shaded by umbrellas. The inviting water reflects blue skies, while a colorful float adds a playful touch. Comfortable seating is arranged around the pool, creating a relaxed outdoor atmosphere.

4.88 out of 5 average rating, 169 reviews

Spring is in the air - HTD Pool*Hot Tub*Game RM

Elevated Hospitality, Thoughtfully Delivered Experience true white-glove hospitality. Our dedicated team responds within minutes, with hands-on management and a quality inspector ensuring every detail is thoughtfully prepared before you arrive. Throughout your stay, we remain available and attentive to any need—so you can relax and enjoy a seamless, comfortable experience. Welcome to Villa Delfino—your sunny island escape with spring breezes, perfect temperatures, and endless sunshine.

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, 112 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.

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, 107 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.

5 out of 5 average rating, 24 reviews

Pool & Sand Volleyball | 3 Kings | Near AMI & IMG

Escape to Two Palms, a spacious 4-bedroom, 3-bath retreat in Bradenton, Florida. Perfectly located just minutes from the sugar-sand beaches of Anna Maria Island. Designed with comfort and relaxation in mind, this home offers everything you need for a memorable getaway. Step inside to an open-concept living space filled with natural light and plenty of space to unwind. Outside, enjoy a private salt-water pool and a beach sand backyard featuring a sand volleyball court.

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.

4.96 out of 5 average rating, 135 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 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.

4.95 out of 5 average rating, 214 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, 127 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!

An aerial view captures a kidney-shaped pool surrounded by lush greenery and vibrant landscaping. Lounge chairs are positioned nearby, while an umbrella offers shade. The pool design includes a spa area, contributing to a serene outdoor atmosphere.

4.92 out of 5 average rating, 331 reviews

Palm Retreat Gold: Luxury Edition of #1 Rental

High end, luxury 3/2 pool home! 7 4k TVs w/ Netflix and cable (75" in living room), SONOS throughout house/pool, wifi, PS5, private heated salt water pool/Spa, putt putt, foosball, beach gear, Pack & Play, Game room (board games, billiards, shuffle board, arcade), massive kitchen/bar, washer & dryer, garage parking-- all in a quiet and safe neighborhood. Just 5 miles to the best beaches and restaurants. Entire home with no shared amenities!

Popular amenities for West Bradenton rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A tiki bar with thatched roofing is showcased, featuring a wooden bar adorned with colorful tiki carvings. A sign reading 'Attitude Adjustment Time' is visible, with comfortable seating nearby. The private pool can be seen in the background, enhancing the tropical atmosphere.

4.93 out of 5 average rating, 86 reviews

Pool + Tiki Bar + Pickleball + Anna Maria Beaches!

Superhost

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.

4.91 out of 5 average rating, 86 reviews

IMG Academy- Updated Home with 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, 58 reviews

Modern 3BR Retreat + Anna Maria Beaches + IMG!

A serene outdoor scene showcases a beautifully designed pool surrounded by lush palm trees. The pool is framed by paver patio and features a space for seating with a small table and chairs. Vibrant plants add natural color to the area.

4.95 out of 5 average rating, 65 reviews

Palmy Private Backyard + Near AMI + Heated Pool

4.83 out of 5 average rating, 64 reviews

6BR 5mi to Beach • Htd Pool • Theater • Game Room

4.86 out of 5 average rating, 92 reviews

4/2 Home Heated Pool/close to Anna M. Beaches/ IMG

4.97 out of 5 average rating, 73 reviews

Pool, mini golf, pickleball, sport court, hot tub

5 out of 5 average rating, 21 reviews

4BD Oasis Sleep 21 Htd Pool, HotTub, Pickle&B-Ball

Apartment rentals with a pool

Apartment in Holmes Beach

The living area features a seating arrangement with two blue sofas and a light coffee table. A ceiling fan is present, along with a beige recliner. Large glass doors open to a lanai, allowing natural light to fill the room, complemented by coastal-themed art on the walls.

4.98 out of 5 average rating, 101 reviews

A Coastal Retreat Steps From the Sea

4.97 out of 5 average rating, 368 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.

4.97 out of 5 average rating, 200 reviews

Luxury 3/3 Margaritaville Resort

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, 126 reviews

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

Apartment in Longboat Key

4.88 out of 5 average rating, 127 reviews

Sunset and beach view from your balcony Unit 403

Apartment in Longboat Key

4.98 out of 5 average rating, 229 reviews

Sun-Kissed Memories!

The dining area features a wooden table set for four, complemented by a light fixture above. A comfortable sofa is arranged in the living area, with sliding glass doors providing views of the greenery outside. Artwork adorns the walls, enhancing the ambiance.

4.98 out of 5 average rating, 237 reviews

Shorewalk full condo IMG Beaches Anna Maria

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, 199 reviews

The Seashell Cottage with peaceful water views!

Other holiday rentals with a pool

5 out of 5 average rating, 15 reviews

A private pool area is showcased within a screened enclosure, featuring clear waters and sun loungers. Colorful umbrellas in red and green provide shade, while tall palm plants are arranged around the space. The adjacent home showcases large windows, offering views of the inviting outdoor area.

Home in Arlington Park

Sarasota's Luxury Oasis

5 out of 5 average rating, 25 reviews

Private Resort with Heated Pool and Sport Court

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, 24 reviews

Luxury Coastal Getaway, minutes from AMI!

4.94 out of 5 average rating, 51 reviews

Htd Pool & HotTub, 6mi to beach, Spotlessly Clean

A screened-in patio surrounds a tranquil swimming pool, offering a peaceful setting. Lounge chairs are positioned along the poolside, with a green lawn and tall palm trees visible in the background. Natural light enhances the inviting atmosphere of the private outdoor space.

5 out of 5 average rating, 47 reviews

Three Bedroom Jungle Paradise with heated pool

4.97 out of 5 average rating, 30 reviews

FALL IN LOVE! Modern pool home mins from the beach

Superhost

5 out of 5 average rating, 3 reviews

Rest Easy, Htd Pool, Tiki Hut, 11 min to Beach

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.