Vacation rentals with a pool in Bradenton

A serene backyard is viewed from above, featuring a well-maintained lawn that gently slopes toward a tranquil pond. Nearby, two cornhole boards are positioned on the grass, surrounded by lush greenery and flowering plants. A white fence outlines the property.

5 out of 5 average rating, 81 reviews

Close to IMG + Pool + Outdoor Kitchen & Projector!

Welcome to Happy Daze! ☀️😎A spacious 3-bedroom, 2-bathroom Heated Saltwater Pool home with outdoor kitchen nestled on a peaceful lake only 5 miles to the picturesque Anna Maria Island beaches. This inviting residence offers accommodations for up to 7, making it an ideal retreat for families & friends. 5 miles - Anna Maria Island Beaches 3 miles - IMG Sports Academy 3 miles - Downtown Bradenton 1 mile - Hiking, 20 Covered Pickleball Courts, Disc Golf, Playgrounds & Skate Park at GT Bray Park.

5 out of 5 average rating, 12 reviews

An inviting outdoor space features a heated pool, surrounded by a screen enclosure for added comfort. Sun loungers are positioned nearby, and cozy seating is available on one side, offering a peaceful environment to relax among nature.

Guesthouse in Bradenton

Guest House with Hot tub & Heated Pool

Welcome to your serene retreat in sunny Florida! This beautifully finished 1-bedroom, 2-bathroom mother-in-law suite offers luxury, comfort, and privacy. With a heated pool and hot tub, we offer year round outdoor relaxation. Step into your own private oasis with a separate entrance and secluded patio, ideal for morning coffee or evening relaxation. Located in a quiet neighborhood backing up to a protected preserve, offering peace and natural beauty. Beach gear provided for easy beach days.

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!

4.98 out of 5 average rating, 166 reviews

SLeePs18+2babyCrib-Hotub-2kingSuites-IMG-picklbal

We sleep 18 adults comfortably plus have 2 baby cribs, so can sleep 20! 5 BEDROOMS!!! NEW PICKLEBALL COURT- new mini golf course- Kids playground- Hot tub- bunks with tube slide- Arcade room- pool table and more! ▪️2Game Rooms ▪️2KingSuites ▪️7miles to Beach ▪️Blackout curtains ▪️BabyMonitor▪️Crib on wheels AND PackNPlay ▪️HighChair ▪️beach chairs▪️pool table▪️hot tub ▪️pickleball▪️RokuTV’s▪️Self Checkin ▪️AirHockey ▪️Grill ▪️FirePit ▪️Washer/Dryer ▪️CoffeeBar▪️Cable ⭐️No Checkout List⭐️

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.

4.96 out of 5 average rating, 55 reviews

FREE Heated Pool, Multiple King BRs, IMG Nearby

Welcome to the beautiful & cozy Bradenton Boho Bungalow near the historic Bradenton Country Club! One of the BEST locations to get around. Located on a very safe & quiet residential street with LOW traffic. Perfect for your family destination! We also provide FREE pool heat! *5 min to tons of shopping & dining *8 miles to Anna Maria Island / beaches *Close to Downtown Bradenton and Riverwalk *5 min to LECOM Field *10 min to IMG Academy *15 min to the Sarasota Airport

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.

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!

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.

4.84 out of 5 average rating, 57 reviews

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

Experience the ultimate Florida retreat in Northwest Bradenton! Discover this delightful 3-bedroom, 3.5-bathroom house. With Palma Sola Bay steps away and Robinson Preserve nearby, this charming vacation rental blends coastal style with traditional Florida charm. Immerse yourself in the tranquility of this picturesque neighborhood and create unforgettable memories!

A serene backyard scene is highlighted by a sparkling pool, accompanied by lounge chairs and a hammock nestled among lush trees. The stylish bungalow features a spacious deck, creating an inviting atmosphere for outdoor relaxation. The sky is painted in calming hues as sunset approaches.

4.97 out of 5 average rating, 33 reviews

10 min AMI | 15 min IMG | Heated Pool

Escape to paradise in this beautifully designed 2-bedroom, 2-bathroom bungalow, located in the heart of sunny Bradenton just 10 min to Anna Maria Island. This chic and tranquil retreat boasts modern comforts and coastal charm, offering the perfect getaway for relaxation and rejuvenation.

Popular amenities for Bradenton rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 3 reviews

Glow in the dark game rm/HTD pool/Pool Table85”TVS

Home in Indian Beach-Sapphire Shores

An outdoor space showcases a heated saltwater pool with a calm blue hue, surrounded by comfortable lounge chairs. The area is framed by lush greenery and fencing, enhancing privacy. The backdrop features a gently lit sky at dusk, complementing the home's modern design.

4.95 out of 5 average rating, 100 reviews

Retreat by the Bay-Heated Saltwater Pool

5 out of 5 average rating, 3 reviews

Breezy Livin' - Speakeasy - Pool - Spa - Game Room

4.93 out of 5 average rating, 152 reviews

The enclosed Florida room features comfortable outdoor furniture, with colorful cushions adorning the seating. A wooden coffee table is positioned in the center, and large windows provide views of the pool area outside, allowing natural light to fill the space.

Home in South Bradenton

Private Heated Pool | Bradenton Vacation Home

An aerial view captures the surrounding neighborhood by Sarasota Bay, featuring tree-lined streets and waterways. A mix of residential homes is visible, along with green parks and recreational areas, demonstrating the serene coastal environment a short distance from the water.

5 out of 5 average rating, 9 reviews

ON SALE - Canalfront, Pool, Grill, Dock

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.

4.78 out of 5 average rating, 96 reviews

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

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, 92 reviews

Tropical Getaway: Pool, Putting Green,Near Beaches

A covered and screened lanai is equipped with a dining table set for six, complemented by a comfortable conversation area. The inviting outdoor space overlooks a spacious pool and backyard, surrounded by privacy fencing.

4.88 out of 5 average rating, 56 reviews

Free Heated Pool/ Lanai/ Near AMI/Beaches/IMG

Condo 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, 104 reviews

Palms Villa: Cozy & Minutes from Anna Maria Island

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.

Condo 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

4.94 out of 5 average rating, 172 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

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

A well-lit living room features a large sectional sofa adorned with blue and green striped cushions. A glass coffee table is centered on a decorative area rug, while a flat-screen TV is positioned nearby. Sliding glass doors open to a screened lanai, offering views of the outdoor space.

4.81 out of 5 average rating, 36 reviews

*Casa Mia* Fabulous View Mins to Anna Maria Isl

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, 147 reviews

Cozy 2 bed/2.5 bath townhome

4.98 out of 5 average rating, 229 reviews

Condo in Longboat Key

Sun-Kissed Memories!

Other vacation 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.

4.93 out of 5 average rating, 28 reviews

New! Luxurious Retreat w/ Resort Amenities by AMI!

5 out of 5 average rating, 6 reviews

Heated Pool Retreat Near IMG & Anna Maria Island

4.94 out of 5 average rating, 51 reviews

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

An enclosed pool area features a spacious swimming pool surrounded by potted plants. Lounge chairs are positioned around the pool, complemented by decorative pink floats. The outdoor space is shaded by a mesh screen, with palm trees visible in the background.

4.97 out of 5 average rating, 76 reviews

Useppa Villa

4.92 out of 5 average rating, 37 reviews

Home in Cortez

Oceanfront | Pool, Dock & Boat Lift Near AMI & IMG

5 out of 5 average rating, 45 reviews

Freshly Renovated Vacation Villa at Shorewalk

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.

4.95 out of 5 average rating, 64 reviews

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

A single-story home is framed by a green lawn and shaded by large trees. The exterior features a light blue color with a red roof. A driveway leads to a one-car garage, and a wooden fence provides privacy in the background.