Holiday rentals with a pool in West Bradenton

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!

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.

5 out of 5 average rating, 59 reviews

Waterfront Bungalow• Dock•Heated Swim Spa•Near AMI

Watch for dolphins and manatees from your private dock and unwind under the stars in the heated swim spa. This peaceful waterfront bungalow near Anna Maria Island is a five-star favorite; perfect for couples or families craving calm, comfort, and coastal charm. Enjoy direct water access for boating or paddling, stunning bayou views, and quick access to beaches, shops, and dining. 🚤 Bring your boat or jet skis • 🌴 5 min to Robinson Preserve • 🏖️ 10 min to AMI • 📶 Fast Wi-Fi | Smart TV

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 serene backyard features a heated pool with a sun shelf and a hot tub, surrounded by lounge chairs and a hammock. Ambient lighting highlights the lush greenery, creating a relaxing space for gatherings or quiet moments.

4.96 out of 5 average rating, 137 reviews

~Kokomo~ Heated Pool/Spa, Games, Fire Pit, Playset

Off the Florida Keys, there's a place called Kokomo, that's where you wanna go to get away from it all...Relax with the whole family at Kokomo House! Bask in a lush, one-of-a-kind backyard with a HEATED pool/hot tub, outdoor dining, fire pit, lounge chairs, & hammock. Play bocce ball, cornhole, foosball, darts, board games, Ms Pacman or on the slackline swingset. 6 miles from Anna Maria Island, 5 miles from IMG, & 4.5 mi from LECOM Park and ½ mi from Manatee River boat ramp.

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.

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, 204 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 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!

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!

4.93 out of 5 average rating, 173 reviews

Casa Noir | POOL • BBQ • FIRE PIT • GAMES • VIBES

Welcome to Casa Noir ! Your private, photoshoot worthy retreat! Lounge by the sparkling pool beneath the angel-wing mural, unwind on the swing daybed by the fire pit, or level up your stay with air hockey, arcade games, and a bike workout in screened in lanai while you watch the kids in the pool. Every corner is designed for fun, style, and that perfect photo moment for the Gram. No other stay vibes quite like this one!

A clear blue pool reflects the sky, with four white lounge chairs arranged nearby on a sunlit patio. Lush green grass surrounds the pool area, complemented by a large tree offering shade in the background. The scene conveys a serene outdoor space for relaxation.

4.9 out of 5 average rating, 136 reviews

Palma Sola Pool Home, minutes to AMI

Welcome to this beautiful home that has been all newly renovated. You’ll be greeted with an open and bright space with beautiful 4 panel french doors leading into the oversized backyard. Location is ideal, a quick 4.3 mile drive takes you to Holmes Beach on Anna Maria Island, 10 minutes to IMG academy, local restaurants and stores, Publix, Fresh Market are all just around the corner from the home.

Popular amenities for West Bradenton rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An aerial view of the outdoor space reveals a heated saltwater pool shaped like a lagoon, surrounded by lounge chairs and umbrellas. A full-size pickleball court takes center stage, complemented by a nearby mini-golf putting green and a trampoline, all set within lush landscaping.

4.91 out of 5 average rating, 22 reviews

New! Luxurious Retreat w/ Resort Amenities by AMI!

5 out of 5 average rating, 5 reviews

FUN! - 12 min to Beach, 10 min to IMG, Heated Pool

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.

4.95 out of 5 average rating, 58 reviews

Gone Coastal - private heated pool near AMI/beach

5 out of 5 average rating, 47 reviews

Salt Pool & Hot Tub+Game Room+ Fenced Large Yard

4.78 out of 5 average rating, 270 reviews

Tropical Oasis - Private Pool - Close Beaches

A landscaped area features a naturalistic waterfall flowing into a small pool. Surrounding the pool are artificial grass and textured stone structures. Lush greenery frames the scene, enhancing the outdoor setting. A small toy boat is placed at the edge of the water.

4.96 out of 5 average rating, 135 reviews

Come as you are... Stay awhile... Florida awaits.

The image showcases a vibrant backyard area featuring a heated swimming pool under a screened enclosure. Comfortable seating is arranged, and a private mini golf course is visible. A separate game room with entertaining equipment like shuffleboard and a colorful mural is also displayed.

5 out of 5 average rating, 47 reviews

Heated Pool•Mini Golf•Arcade•Spa•AMI 6mi•IMG

An inviting outdoor pool area features upgraded lounge chairs set beside a clear, private pool. A dining space is positioned under the screened enclosure, allowing for enjoyable gatherings. The sunset sky in the background adds a tranquil ambiance, enhancing the outdoor relaxing experience.

4.92 out of 5 average rating, 77 reviews

Tropical Getaway: Pool, Putting Green,Near Beaches

Condo rentals with a pool

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

An open kitchen features a dark granite countertop with seating for two. A set of pendant lights hangs above, illuminating the space. Modern appliances and warm wood cabinetry create a functional cooking area. A welcoming sign is displayed on the wall near the laundry machines.

4.85 out of 5 average rating, 137 reviews

Shorewalk upgraded condo upstairs unit 4415

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

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! Condo with pool 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

Other holiday rentals with a 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

A heated pool is surrounded by a screened lanai, providing a bug-free zone. Outdoor loungers are positioned nearby, and a cozy seating area offers plush chairs. Lush greenery is visible in the background, ensuring privacy and a tropical feel.

4.92 out of 5 average rating, 24 reviews

Free Early Check-in / Min to Beaches/ Heated pool

Superhost

5 out of 5 average rating, 3 reviews

Heated-Pool • Near Beaches • Arcade Game Room

5 out of 5 average rating, 43 reviews

Freshly Renovated Vacation Villa at Shorewalk

5 out of 5 average rating, 12 reviews

4BD Oasis Sleep 21 Htd Pool, HotTub, Pickle&BBall

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

The outdoor area features a screened-in pool surrounded by a spacious travertine patio. A heated saltwater pool is illuminated under the evening sky, with lounge chairs and a dining area visible. The interior opens to the patio, enhancing the connection between indoor and outdoor spaces.

4.99 out of 5 average rating, 81 reviews

Winter Specials! Near AMI & IMG~Heated Salt Pool

A serene bedroom features a spacious bed dressed in light linens, accompanied by bedside tables with lamps. Natural light filters through a window, while a neutral-toned rug adds warmth. A pair of chairs and a small ottoman provide a cozy reading nook.