Vacation rentals with a pool in Bradenton Beach

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Top-rated rentals with a pool in Bradenton Beach

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Bradenton

4.87 out of 5 average rating, 205 reviews

Sunny Oasis Near Beaches With Pool

Shore's Oasis is minutes to Anna Maria Island and the gulf beaches. Our modern beach-style home features a lovely pool, barbecue area, porches, comfortable furnishings and fun decor. We are located close to the Cortez Fishing Village, restaurants, shopping, live music, rental shops, tours and Florida fun! As Bradenton, Florida natives we are happy to guide you towards a unique experience in our local community so that you don't miss a thing while you are visiting. Safe travels and see you soon!

Aug 19 – 26

R2,938 ZAR per night

Guest favorite

Home in Bradenton Beach

4.97 out of 5 average rating, 153 reviews

Paradise! Steps2 Private Beach & Tropical Yard!

Less than a 2 minute WALK from the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. With large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with a bathroom on opposite ends of the house (a pocket door adds privacy). Private heated salt water pool sits amidst the lush tropical yard. Hop on the free A/C'ed trolley and explore Florida's gorgeous Anna Maria Island.

Apr 26 – May 3

R12,753 ZAR per night

Guest favorite

Tiny home in Bradenton

4.95 out of 5 average rating, 308 reviews

Tiny Carriage House-Pool, Riverwalk, Downtown

In the historic district of Bradenton's riverside downtown the 2nd story 1898 Carriage House Retreat is an intimate 1room studio for a romantic weekend, a friends' getaway or business travelers. Fully renovated with every modern amenity, yet preserving its antiquity, it nestles behind our 1898 Queen Anne Victorian where we live. Where the horse and buggy would have been kept, the Carriage House sits with it's own private driveway & within steps of downtown's eateries, pubs, shopping & more!

Oct 16 – 23

R3,117 ZAR per night

Guest favorite

Condo in Longboat Key

4.93 out of 5 average rating, 145 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf of Mexico and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

Aug 16 – 23

R5,700 ZAR per night

Guest favorite

Condo in Bradenton Beach

5.0 out of 5 average rating, 17 reviews

AMI Perfect Experience

This condo has been designated as a Guest Favorite. This beautiful ground floor condo offers the best experience and perfect vacation getaway in Anna Maria Island for up to 4 guests. Located steps from the beach, this condo has exceptional value with its amenities, including the largest heated pool on the island, tennis courts, pickleball, bocce ball, workout room, beach chairs, umbrella, noodles, and wagon for those looking to stay active. It has everything you need including location!

Apr 28 – May 5

R3,231 ZAR per night

Guest favorite

Condo in Tierra Verde

4.96 out of 5 average rating, 238 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Feels like the Florida Keys! Fully renovated & well appointed second floor, 1 bed, 1 bath condo in Holiday Island condo resort. The condo features a beautiful waterfront & pool view, tennis, bicycles, hot tub, dock with grills, gym, and more. Remodeled in 2015 the condo features a fully equipped kitchen, Keurig coffee maker, beautiful views from the living room, dining room, kitchen, balcony. Walking distance to many local restaurants & minutes away from St. Pete Beach & Fort DeSoto.

May 26 – 31

R2,330 ZAR per night

Superhost

Condo in Bradenton Beach

4.86 out of 5 average rating, 102 reviews

Charming and Updated 1 Bedroom in Runaway Bay

Our charming 1 BR/ 1 Bath condo is a new to the rental market. It was formerly owner occupied. The property is in the Bradenton Beach area of Anna Maria Island. Beach is right across the street with deeded access. The pool is the largest heated pool on the island. Fitness center has newer equipment. There is a fishing pier which also works as a great way to enjoy beautiful views of the Anna Maria sound. Free trolley stop is right in front of the property. Washer/dryer in unit.

Sep 15 – 22

R4,515 ZAR per night

Guest favorite

Condo in Bradenton

4.94 out of 5 average rating, 108 reviews

Newly remodeled cozy 2 bed/2.5 bath townhome

Fully renovated 2 bedroom/2.5 bathroom townhome nestled in a quiet, gated community in Bradenton between I-75 and some of the best beaches in the country. My townhome features 2 bedrooms (queen size) with en suite bathrooms. Beds are queen size. Amenities in the neighborhood include: large heated pool, tennis and basketball courts, playground, volleyball area, sport field, and designated parking spot steps away from the front door. Non-numbered guest parking is also available.

Dec 14 – 21

R3,221 ZAR per night

Guest favorite

Bungalow in Anna Maria

4.88 out of 5 average rating, 121 reviews

Bay Breeze Cottages #2 (The Redfish)

Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.

Dec 11 – 18

R5,456 ZAR per night

Guest favorite

Guesthouse in Sarasota

5.0 out of 5 average rating, 102 reviews

Magical Guesthouse 1 mi from SRQ airport

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

Nov 16 – 23

R2,632 ZAR per night

Superhost

Home in Bradenton

4.83 out of 5 average rating, 18 reviews

"Paradise" by the Private (Heated) Pool light!

Perfect Couple's Getaway "Paradise" with Private Heated Pool in Very Secluded Tropical Backyard! Large Screened in Lanai, BBQ Grill, Bonus Outdoor Shower, Lounge Chairs, Washer & Dryer, Wi-Fi, Smart TV, Queen Bed, Kitchenette (comes complete with everything you need to cook, make coffee, etc.), Mini Fridge/Freezer, Breakfast Bar with Seating for Two, Updated Bathroom. Located 1 Mile from the Beautiful Gulf Coast and Beaches.

Oct 21 – 28

R2,783 ZAR per night

Guest favorite

Condo in Bradenton

4.98 out of 5 average rating, 170 reviews

Shorewalk full condo IMG Beaches Anna Maria

1174 Sqft first floor 2 bedroom and 2 bathroom with a nice kitchen full condo in the beautiful Shorewalk community. Within very short walking distance to movies, groceries ,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

Aug 11 – 18

R2,692 ZAR per night