Vacation rentals with a pool in Bayshore Gardens

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Top-rated rentals with a pool in Bayshore Gardens

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Guest favorite

Home in Sarasota

4.9 out of 5 average rating, 107 reviews

🌴🐬Bay Haven- Resort style Backyard 🏊‍♀️🔥 & Game Rm⚽️

Welcome to "The Bay Haven" - a family friendly vacation villa with a view of Sarasota Bay! Relax in our luxurious 2350 sq. ft. single-level home boasting an open floor plan and a 600 sq. ft. rec room stocked with family games & entertainment. The home is fully remodeled with high-end finishes and designer touches. Enjoy the backyard oasis, including a large heated pool, firepit, plenty of seating and a grill. It’s an easy drive to the white sand beaches of Siesta Key and Anna Maria Island.

Nov 5 – 12

R12,760 ZAR per night

Guest favorite

Home in Bradenton

4.97 out of 5 average rating, 38 reviews

NEW! Relaxing Cottage Near Anna Marie Island

Relax and enjoy easy access to everything from this centrally located home. Located in an RV resort just 3 miles from Sarasota airport and 6.5 miles from Anna Maria Island, you will enjoy some of the most beautiful beaches and sunsets on the gulf! Conveniently located between St. Pete and Siesta Key. This kid friendly community offers: a swimming pool, pickle ball court, shuffle board, horseshoes and a fitness center just steps away from the home’s front door. Cot & crib available if needed!

Sep 5 – 12

R2,495 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

R3,186 ZAR per night

Guest favorite

Guest suite in Bradenton

5.0 out of 5 average rating, 13 reviews

Waterfront Suite-20 min to Gulf Beaches

A hidden gem awaits you in this waterfront “Old Florida” style guest suite. You’ll be in a separate suite with your own entrance, bedroom & cozy living area. The setting offers amazing days swimming in the pool, paddle boarding, fishing or boating. Maybe you’ll see manatees in the creek or the ducks, turtles, our cats & resident Blue Heron parade around the property. Beach lovers can get to the gorgeous gulf beaches of AMI in about 20 minutes. Nightlife? We’re 15 min from downtown Sarasota.

Oct 13 – 20

R2,463 ZAR per night

Guest favorite

Condo in Bradenton

4.95 out of 5 average rating, 129 reviews

The Seashell Cottage with peaceful water views!

Hello and welcome to my beautiful Seashell Cottage! I have completely renovated and remodeled this townhome for you! It has a new kitchen and bathroom, new vinyl plank flooring upstairs, new furniture and bedding throughout, and is freshly painted. Decorated in a turquoise beachy decor, it gives you a sense of peace and tranquility the moment you step inside! There are gorgeous water views of the lake from both the first and second floor. Enjoy your private hammock on a seashell beach!

May 28 – Jun 4

R3,110 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.

Nov 26 – Dec 3

R3,292 ZAR per night

Superhost

Home in Bradenton

4.87 out of 5 average rating, 114 reviews

Backyard Oasis Heated Pool W/Tiki Bar,Close To IMG

Welcome to your West Bradenton Private Resort ! This gorgeous home has been completely renovated with an OPEN Concept layout, Brand New Salt Water Heated Pool, and Tiki Bar w/ Wet bar next to the pool! Located 5 Minutes from IMG Academy and 15 Minutes from Anna Marie Island. just 5 miles from SRQ airport and 10 minutes to both downtown Bradenton and Sarasota. This home has four good sized bedrooms. HIGH Speed WiFi! FREE Off Street Parking! YoutubeTV w/ NFL Ticket poolside!

Jul 16 – 23

R5,574 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

Aug 28 – Sep 4

R3,358 ZAR per night

Guest favorite

Guesthouse in Sarasota

4.89 out of 5 average rating, 168 reviews

Supercute Beach Themed Retreat Free Parking Wi-FI

Come and enjoy our newly remodeled 400 square foot laid back beached themed guest house. Located just 1.5 miles away from Sarasota/ Bradenton airport, and less than 10 miles away from our world famous beaches. Whether you are a single person in search of a long term stay or a family looking for a short vacation, we have the place for you. Our guest area is attached to our main residence and has a private entrance. Enjoy our shared swimming pool and outside patio areas.

Mar 5 – 12

R2,549 ZAR per night

Guest favorite

Cottage in Bradenton

4.96 out of 5 average rating, 98 reviews

Coastal Style 2BR cottage near Anna Maria Island

Relax with the whole family at this peaceful place to stay. Located in a mobile home/RV park 6.5 miles from Anna Maria Island, which offers some of the most beautiful beaches on the gulf coast. Centrally located between St. Petersburg and Siesta Key. This kid friendly community offers many amenities such as Pickle ball, swimming pool, shuffle board, horseshoes and gym on site. Stay a few days or a few months! Snow birds are welcome! Only 3.3 miles to Sarasota Airport.

Oct 18 – 25

R2,877 ZAR per night

Guest favorite

Guesthouse in Sarasota

4.99 out of 5 average rating, 131 reviews

Maggie's Hideaway

This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!

Aug 13 – 20

R2,515 ZAR per night

Guest favorite

Guest suite in Bradenton

5.0 out of 5 average rating, 188 reviews

Off Anna Maria Island ~10min to beach w/salt pool

Stay close to the beach and like a local at Off Anna Maria, a cozy, private guest suite attached to our home with separate entrance, saltwater pool, and shaded outdoor patio. Located ~10 mins from Anna Maria Island, 45 mins from Siesta Key, 1 hr from Tampa in a quiet suburban neighborhood. Your interior space is completely separate from ours. The pool and patio are shared with us. *Travel time estimates depend on traffic.

Jul 20 – 27

R2,130 ZAR per night