Vacation rentals with a pool in Downtown, Sarasota

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Downtown, Sarasota

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

0 of 0 items showing

1 of 3 pages

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

ﺩ.ﺇ460 per night

Guest favorite

Guest suite in Sarasota

4.94 out of 5 average rating, 286 reviews

Beach & Town Posh Location! Jungle Paradise Studio

PRIME Town/Beach 3.2 miles location! *COVID Cleaning. SELF CHECK IN. Non shared Pool. Bungalow w/private entrance & patio. Designers Home,Tropical Jungle, like Posh Resort! Quiet, residential area. Sought-after amenities. 10 min/Siesta Key Beach, shops, dining, & 5mins/Downtown Sarasota core. Walk to local markets, dining, movies & shopping. New King bed. New 50" TV. Off street parking. No Smoking/Vaping! Wet Bar, No kitchen, lite meals only! No hotels in my exclusive area! Live like a local!

Sep 19 – 26

ﺩ.ﺇ675 per night

Guest favorite

Bungalow in Sarasota

4.92 out of 5 average rating, 310 reviews

Pool & fenced-in yard in downtown edge bungalow

This 2 bed-2 bath house is a homey Florida bungalow with cypress wood floors and lots of natural light, located in a quiet neighbourhood on the downtown core edge. Enjoy a spacious and fenced in backyard with pool, covered grill and eating area. The home is minutes away from the Legacy Trail, the new Bay Park, Payne Park, dining, live music, bars, theatres, opera house, performance venues, comedy club, antiquing, kayak launches, tennis and basketball courts, farmer's market, shopping and more.

Jan 28 – Feb 4

ﺩ.ﺇ831 per night

Guest favorite

Condo in Sarasota

4.96 out of 5 average rating, 121 reviews

Lido-Key- Tiny Studio Holiday Cottage-A

**No Kids allowed** Lido Key- 7-10 min walk to the beach & St Armands. Quaint main floor tiny (smaller than a hotel room) studio is in a Great location and an affordable way to enjoy this popular area. This cozy cottage features a Queen size bed, refrigerator, stove, microwave, coffee maker, washer & dryer, and fully stocked cooking items & dishes, There is a pull-out large kitchen table. Beach chairs, umbrella & towels are provided. Located at 170 Roosevelt Dr Drive, Sarasota, Fl 34236.

Dec 1 – 8

ﺩ.ﺇ559 per night

Guest favorite

Home in Sarasota

4.97 out of 5 average rating, 100 reviews

Sunshine House, close to Downtown Sarasota

Great location! This is a family friendly home, close to downtown and beaches, with a pool, fenced yard, and a large screened porch for lounging and having meals outside. Close to all the great things Sarasota has to offer- museums, gardens, theaters, shopping, Sarasota Bay, and beaches. The house is 1.5 miles from downtown, 10 min to St. Armands, 15 min to Lido Beach, and about 20 min Siesta Key Beach. One dog considered with a fee. Children must be supervised at all times in the pool area.

Oct 22 – 29

ﺩ.ﺇ786 per night

Guest favorite

Guest suite in Sarasota

4.99 out of 5 average rating, 196 reviews

The Artist Studio SRQ

The Artist Studio is a studio guest-suite connected to our home but completely separate from the main house. Guests have a private entrance with keypad lock while the space has been soundproofed for privacy. Once the studio of an artist who created large abstract paintings it has been converted to a wonderful studio apartment with 15 ft. ceilings and lots of sunlight. Conveniently located walking distance to Bayfront Park, Selby Botanical Gardens, Downtown Sarasota & the Sarasota Art Museum.

Oct 12 – 19

ﺩ.ﺇ773 per night

Guest favorite

Home in Arlington Park

4.95 out of 5 average rating, 410 reviews

The Cottage At Central Park

There is no more charming place to stay! From the minute you step inside this immaculate and cozy private residence you will feel right at home. With a beautiful open kitchen, natural light that pours into every room, a spacious back porch overlooking the pool and fenced in yard with a fire pit, this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!

Feb 13 – 20

ﺩ.ﺇ1,264 per night

Guest favorite

Home in Sarasota

4.93 out of 5 average rating, 150 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 bedrooms & baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown and more. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack.

Aug 25 – Sep 1

ﺩ.ﺇ2,142 per night

Guest favorite

Guest suite in Sarasota

4.95 out of 5 average rating, 59 reviews

Beautiful poolside studio

Relax and enjoy the beauty of Sarasota at this peaceful and centrally located studio. Your space opens to an inviting Mediterranean style cocktail pool and backyard oasis. Walk to downtown Sarasota which boasts great restaurants, shops, the opera, ballet, and the Bayfront or walk to Gillespie Park and enjoy the tennis and pickle ball courts. The studio is just a short drive to Sarasota's award winning beaches, Selby Botanical Gardens, Ringling Museum of Art and Ca' d'Zan.

Oct 28 – Nov 4

ﺩ.ﺇ679 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.

Nov 12 – 19

ﺩ.ﺇ386 per night

Guest favorite

Apartment in Sarasota

4.86 out of 5 average rating, 14 reviews

Apartment in Sarasota

Take a break and unwind at this peaceful oasis. This Condo is located near Lido Beach, Downtown Sarasota, St. Armand's Circle and SRQ Airport. Come home after a day at the beach, or a walk in Downtown and relax in the big public pool, hot tub, fire pit, barbecue grills, and modern gym. Sarasota had a lot to offer. Sarasota has UTC mall, Marie Shelby Gardens, and Jungle Garden. There are numerous other fun activities to do with your family in Sarasota.

Jun 15 – 22

ﺩ.ﺇ568 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 15 – 22

ﺩ.ﺇ487 per night