Holiday rentals with a pool in Bradenton

4.77 out of 5 average rating, 258 reviews

Tropical Paradise - Private Pool - Close Beaches

Relax in a tropical Pool Home. With beautiful palms and an over-sized private pool. This beautiful pool home is only a short drive to Anna Maria Island. Floridas beautiful white beaches on the Gulf of Mexico. Pool heating available. Huge master bedroom with attached full bath and access to the pool area. Free high speed WIFI. 55" Smart TV in living room and a second Smart TV in the queen room. 2 parking spaces. Convenient to beach bars, golf, shopping. 25 Min. Sarasota and 45 Min. Tampa Airport.

4.96 out of 5 average rating, 103 reviews

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

4.98 out of 5 average rating, 142 reviews

Near downtown! Saltwater Pool! HOT TUB! Games!

Beach! River! Heated Saltwater Pool! Hot Tub! Your tropical beach vacation awaits! Prime location in proximity to local restaurants, attractions & sparkling waters. Nathan Hejl Interior Designer has updated this spacious 5BR/3.5BA vacation oasis to blend luxurious furniture & finishes w/ a barefoot, tropical vibe. Located in Historic River District in W Bradenton, walking distance to Manatee River, 2mi to Bradenton Convention & only 8mi to the famous Anna Maria Island beaches, 20mi to #1 Siesta

5 out of 5 average rating, 17 reviews

5BR W/ New Pool! 6mi to AMI Beach & IMG Academy

Experience the Bradenton and Anna Maria Island area in this new modern 5-bedroom 2.5 bath retreat. Featuring a screened in lanai off the main living area overlooking the brand new salt water pool with tanning ledge. Tropical oasis perfect for multigenerational families and friends ☀ 5 minutes to Robinson Nature Preserve ☀ 10 minutes to Manatee Public Beach (Traffic Dependent) ☀ 14 minutes to IMG Academy ☀ 36 minutes to The Premier Sports Campus ☀ 36 minutes to Bradenton Motorsports Park

5 out of 5 average rating, 52 reviews

Private Backyard + Heated Pool + Luxury Boho Style

Welcome to Palm Haven! A retro-modern-boho style freshly updated home in W. Bradenton with wall-to-wall bay window views to a private pool and secluded palmy backyard patio. Heat the pool up to 90 degrees! Enjoy close access to the Warner Bayou boat launch & the scenic drive to Anna Maria Island (AMI). After your adventures, retreat back to Palm Haven when you need a place to cool off, wind down & relax. Perfect atmosphere & space for families and/or professionals to unwind and break away.

Superhost

4.86 out of 5 average rating, 7 reviews

"Enfuego!"

Take it easy at this unique and tranquil getaway, with 6 bedrooms and 4 bathrooms right next door to IMG and only 5 miles from the beach! This house consists of 3500 square ft of living area, heated pool, waterfall, golf simulator, movie theater and gaming area. “En Fuego” sleeps 18 people when you add in our custom loft beds! This place is FIRE 🔥 literally with 8 fire features and its own private poolside beach. Bring the whole team and enjoy your stay at En Fuego today!

4.91 out of 5 average rating, 370 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.

4.96 out of 5 average rating, 180 reviews

Private Oasis: Heated Saltwater Pool+Putting Green

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!

4.97 out of 5 average rating, 100 reviews

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!

4.97 out of 5 average rating, 327 reviews

Island in Sarasota

NEW 3/NTS JULY OPEN! Sarasota #1 Lux BEACH Villa

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

4.99 out of 5 average rating, 102 reviews

Guesthouse in Bradenton

Private Stock Tank Pool. Cozy Tropical Stay

Cozy tropical retreat just 4.6 miles from Sarasota Airport and 7 miles from the beach. Perfect for two! Enjoy a private stock tank pool, fully equipped kitchen, comfy bed, fast Wi-Fi, and free parking. Relax in your own peaceful outdoor space and feel the tropical vibe. Ideal for a romantic escape, a beach weekend, or simply to unwind in a unique and private setting.