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.

Sep 18 – 25

G$140,450 GYD per night

Guest favorite

Guest suite in Sarasota

4.89 out of 5 average rating, 111 reviews

Downtown privacy, beaches and nightlife all around

For the couple (or individual) who wants a fabulous private home and is in a centrally-located space in downtown Sarasota. Where the beaches meet the nightlife (Legacy Trail is 5 short blocks away, pickle ball 3 and Robarts Arena 2), this separate In-Law Suite has its own entrance, private patio and lots of space (1,000 sq. feet). 2 bikes and beach items for use are: chairs, umbrellas, noodles and coolers. The washer/dryer is attached, high-speed internet/cable; there is a gas grill, 2 tvs

Jun 12 – 19

G$26,100 GYD 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!

Jun 5 – 12

G$27,315 GYD 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!

Jan 16 – 23

G$34,125 GYD 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 14 – 21

G$26,969 GYD 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.

Mar 18 – 25

G$45,727 GYD 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!

Jun 9 – 16

G$55,206 GYD 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

Jan 10 – 17

G$37,114 GYD 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.

Jan 23 – 30

G$25,428 GYD per night

Guest favorite

Condo in Bradenton

4.98 out of 5 average rating, 105 reviews

The Seabreeze Cottage with peaceful water views

Welcome to my newly renovated townhouse! The Seabreeze Cottage is a two bedroom, 1.5 bath, colorfully decorated townhouse with a fun beachy vibe! It has beautiful and peaceful water views of the lake. It’s within 30 minutes of the Gulf Coast’s best beaches, including Anna Maria Island, Longboat Key, and Siesta Key. Only ten miles from Sarasota airport (SRQ) and about one hour from Tampa airport (TPA). It’s just 7 miles or 15 min from the world renowned IMG Academy.

Jul 8 – 15

G$40,981 GYD 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 14 – 21

G$27,674 GYD 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 27 – Sep 3

G$29,787 GYD per night