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Downtown Sarasota

One of the most popular communities provided by Michael Graf

Downtown Sarasota

About Downtown Sarasota

Living in downtown Sarasota, Florida offers a vibrant blend of urban sophistication and coastal charm. This lively neighborhood is known for its stunning bayfront views, cultural attractions, and a diverse array of dining and shopping options. Residents enjoy easy access to world-class art galleries, theaters, and festivals that showcase the area’s rich artistic heritage. The nearby sandy beaches provide a perfect escape for sun-seekers and outdoor enthusiasts, while the city's parks and waterfront promenades promote an active, healthy lifestyle. With a strong sense of community and a dynamic atmosphere, downtown Sarasota is not just a place to live; it’s a lifestyle that embraces both relaxation and excitement.

One of the most popular communities provided by Michael Graf

4,366

# of Listings

2

Avg # of Bedrooms

$483

Avg. $ / Sq.Ft.

$857,142

Med. List Price

Browse Downtown Sarasota Real Estate Listings

All listings

$250,000 - $500,000

4366 Properties Found. Page 223 of 292.

Enjoy your vacation on Siesta Key in this spacious three bedroom/two bathroom vacation rental. This condo is turnkey furnished including washer/ dryer and private garage. Guests are walking distance away from private beach access to Siesta Key’s world-renowned white sandy beach on the Gulf of Mexico. Come stay with us and enjoy warm sunny Siesta Key.

**Taxes and fees not included.

SARASOTA

1391 SIESTA BAYSIDE DRIVE 1391-B

3 Beds

2 Baths

1,495 Sq.Ft.

$5,000

MLS#: A4596168

Turnkey Seasonal Rental in Sarasota Harbor East, fabulous bay views from every window, 2 bedrooms, two baths, updated and tile floors throughout. Lovely four season Lanai overlooking Sarasota Bay, watch the Dolphin and Manatee while you sip your morning coffee. The community offers a lovely heated pool, clubhouse, grills, kayak storage and boat slips on a first come, first served basis. Walk to all the shops and restaurants on St. Armands Key, spend the day at beautiful Lido Beach or stroll over the bridge to Downtown Sarasota. You will love this great community and location. This is a 55+ community. Booked end of January thrught the endo of March, 2024.

SARASOTA

769 JOHN RINGLING BOULEVARD 36EXET

2 Beds

2 Baths

1,042 Sq.Ft.

$5,000

MLS#: A4586107

RENTED JAN, FEB. MARCH APRIL 2025: This third-floor vacation condo with absolutely one of the best views in Stoneybrook. Two bedrooms, two baths, king bed in master, queen in the guest bedroom, internet access, flat-screen TVs and a NEW KITCHEN complete with granite countertops. Eating space in kitchen, living room dining room combo, one covered parking space. ALL NEW FLOORING throughout, everything you need for a few months in the sunshine. Golf membership transfers for a fee if desired (check with clubhouse for cost) and the heated pool and tennis courts are right across from the building. Members can dine at the impressive clubhouse, use the fitness center, enjoy the Arthur Hills designed premier golf course, lounge at the pool, play tennis, and enjoy the many activities the club has to offer. Stoneybrook is a gated community conveniently located on Palmer Ranch giving quick access to shopping, banks, restaurants, I-75, and less than 15 minutes to the sugary sandy beaches of Siesta Key. The Legacy Walking and Biking Trail access is just a block from the entrance to the community and it's a short drive to downtown Sarasota.

SARASOTA

9300 CLUBSIDE CIRCLE 1307

2 Beds

2 Baths

1,314 Sq.Ft.

$5,000

MLS#: A4481790

Sunshine, palm trees, majestic oaks, and your own private pool—this beautiful turnkey furnished downtown Sarasota home is ready for your next getaway, available for monthly rental year-round with a 30-day minimum stay—just bring your sunscreen and flip flops! Step inside to an open and inviting living area filled with natural light, flowing seamlessly into the dining space and a well-equipped kitchen with sleek finishes, bar seating, and plenty of cabinet storage. The split-bedroom layout offers three comfortable bedrooms and two full bathrooms. The primary suite includes a walk-in closet and a private bath with an oversized walk-in shower, while the two guest bedrooms share a full bath with a tub. The screened lanai features a heated pool and spa with a sun shelf, surrounded by travertine pavers—perfect for relaxing or entertaining. Beyond the lanai, a fully fenced backyard offers lush turf, a beautiful Live Oak tree, and plenty of space for lounging or playing. Located just minutes from world-famous beaches, shopping, dining, and entertainment. Located just blocks from Downtown Main Street Sarasota with all it has to offer—dining, night life, shopping, arts, and more. Offered in season (Jan-Apr) for $10,000/mo and off-season (May-Dec) for $5,000/mo. All lease terms shorter than 6 months are subject to 13% tourism tax. Sorry—NOT AVAILABLE as an ANNUAL rental. Don't miss the chance to experience Florida living at its finest!

SARASOTA

2141 HYDE PARK STREET

3 Beds

2 Baths

1,709 Sq.Ft.

$5,000

MLS#: A4655596

AVAILABLE OFF-SEASON ONLY, Exceptional 3rd-floor condo in elevator building with great view across golf course and pond from the glass enclosed and screened lanai, beautifully furnished, king bed in master, twins in guest room, well appointed, one covered parking space, pool just across the parking area and golf membership transfer is available for a fee if desired. Stoneybrook Golf and Country Club offers a full service restaurant and is one of Sarasota's most popular golf and tennis clubs. The golf course modernization project is completed and said to be one of the best courses on the West Coast of Florida. Stoneybrook is centrally located on Palmer Ranch and is less than 15 minutes from the sugary sandy beaches of Siesta Key, the village shops and restaurants. For the bike enthusiasts, the access to the Legacy Walking and biking trails is just a block from the community.

SARASOTA

9630 CLUB SOUTH CIRCLE 6309

2 Beds

2 Baths

1,314 Sq.Ft.

$5,000

MLS#: A4619103

Perfectly situated just one block from the heart of Siesta Key Village and a mere two blocks from the pristine white sands of the renowned Siesta Key Beach, this Villa Navarra condominium offers an enviable location. Surrounded by lush tropical landscaping, this rare exclusive gem is one of only 16 units, featuring newer PGT windows and sliding glass doors. Recently renovated with the utmost attention to detail and adorned with the finest finishes and furnishings, it exudes modern elegance. Conveniently situated on the ground floor, you'll enjoy seamless access in and out through your back door, leading directly to your designated parking space. Alternatively, you can hop aboard the complimentary daily trolley, which makes multiple convenient stops throughout Siesta Key. Indulge in the vibrant ambiance of Siesta Key Village, offering an eclectic mix of shopping and dining experiences, from laid-back island-style entertainment to a variety indoor venues. This premium location is conveniently located less than a quarter-mile from Siesta Key Beach. Enjoy America's favorite beach destination with the luxury of a new home feel. ***Available 9/15/25

SARASOTA

137 AVENIDA MESSINA 2

2 Beds

2 Baths

1,016 Sq.Ft.

$5,000

MLS#: A4660899

Kingston Arms on St. Armands Circle turn-key furnished Condo, 2 beds, 2 baths, second floor overlooking a quiet residential street. Look no further for the perfect vacation retreat. No need for a car, walkable to the many fine shops and local restaurants, take the BayRunner Trolley to downtown Sarasota for the day, book a guided Kayak tour through the mangrove tunnels or spend the day at Lido Beach, only a four minute walk! Many dates available and rates vary by season.

SARASOTA

500 S WASHINGTON DRIVE 5B

2 Beds

2 Baths

1,102 Sq.Ft.

$5,000

MLS#: A4604124

#A4543933

SARASOTA

4705 HOLLINGSWORTH AVENUE Lower

3 Beds

2 Baths

1,236 Sq.Ft.

$5,000

MLS#: A4543933

Check out this COMPLETELY REMODELED canal-front pool home on Siesta Key! Picture this: you roll out of bed and grab your coffee, take two steps out of the sliding glass doors, and enjoy it by the saltwater pool. After your coffee, take your morning swim. Then take another 10 steps, or so, and catch some significant fish in the canal which happens to be in your backyard. Chances are that an occasional manatee may swim by for a visit. Fall back into your open-concept home and enjoy a delicious dinner and a great view from your well-equipped kitchen. Oh yes, the pool is open 24-7!

SARASOTA

5577 CONTENTO DRIVE

2 Beds

2 Baths

2,089 Sq.Ft.

$5,000

MLS#: A4607468

RENTED, DEC 2025 JAN THROUGH APRIL 2026: GROUND FLOOR END UNIT at Stoneybrook Terraces, spacious vacation rental with golf course view, bright and cheerful, designer decorated, new carpet, new furnishings, new paint, new appliances, immaculate and offering all you will need for a few months in the sunshine. Golf membership transfers to the tenant if desired. The Terraces has tennis courts and the all-popular pickleball plus heated pool and is the closest community to the impressive clubhouse where you will find a fitness center, large heated pool, and, of course, the newly modernized 18-hole Kipp Schultes premier designed golf course, impeccably maintained, Har-Tru lighted tennis courts and all the activities you would expect from a country club. Stoneybrook is a gated community located on Palmer Ranch just minutes from Siesta Key beaches, shops, and restaurants. The Legacy walking and biking trail is two blocks from the entrance, the YMCA, Publix, CVS, Walgreens, and several banks are nearby.

SARASOTA

8735 OLDE HICKORY AVENUE 8101

2 Beds

2 Baths

1,449 Sq.Ft.

$5,000

MLS#: A4489419

Looking for the ultimate Siesta Key getaway? This stunning 3-bedroom, 2-bath home offers everything you need for a dream vacation, just 1 mile from the famous Siesta Key Beach and a quick bike ride to the lively Siesta Key Village! Available Nov 1-Dec 21, 2025, and May 1-Nov 21, 2026. 30 day minimum stay, NOT available annually. Fully turnkey furnished, this home is ready to welcome you the moment you step inside. The open and inviting great room is perfect for gathering with friends and family, whether you’re relaxing after a day in the sun or entertaining guests. The spacious kitchen, with a cozy dining area off to the side, makes it easy to enjoy meals together. Plus, a laundry room and 2-car garage ensure convenience throughout your stay. Step outside and discover your own private oasis – a large screened lanai featuring an in-ground heated pool, perfect for swimming or lounging under the sun. Whether you prefer soaking up rays or unwinding in the shade, the lanai offers ample space for everyone to enjoy. The privacy-fenced backyard adds a secluded feel, making it the perfect spot to relax in peace. With electric, internet, basic cable, pool service, and grounds maintenance included, all you have to worry about is enjoying your time in paradise. Reach out today to secure your seasonal stay in this desirable Siesta Key retreat! Monthly rates are $5000 May through October, November $5750, December $6750, January through April $8500. 13% tourism tax must be added to all leases 6 months or less. 30 Day minimum term. Sorry, NO ANNUAL leases available, and no pets permitted.

SARASOTA

735 BIRDSONG LANE

3 Beds

2 Baths

2,784 Sq.Ft.

$5,000

MLS#: A4660352

It doesn't get better than this! This condo is roomy, beautifully decorated and fully furnished. Located on the first floor with a private patio with direct access to the pool. Relax and read a book by the pool or jump on the Bay Runner trolley and go to St. Armand's circle. The beach is directly across the street, and the unit has 2 beach chairs and an umbrella. New AC and Water heater and new flooring and freshly painted and updated. Rental includes all utilies. If you ever thought about living the Florida life this is y6ur chance!! All you need to do is pack your suitcase, this condo has everything else. Seasonal pricing is $5000 a month Dec-March

SARASOTA

845 BENJAMIN FRANKLIN DRIVE 102

1 Beds

1 Baths

756 Sq.Ft.

$5,000

MLS#: TB8401738

DOWNTOWN SARASOTA...!ANNUAL UNFURNISHED WATERFRONT CONDO AVAILABLE IN ONE WATERGATE. Stunning views abound from this 1736 Sq. Ft 2 Bedroom, 2 Bath Condo in the heart of downtown Sarasota. The condo features a large wraparound balcony, impact resistant windows, large closets with organizers, and a spacious kitchen with granite countertops. There is also an additional in-unit storage room with cabinets and an additional refrigerator. One Watergate amenities include a heated saltwater pool, grilling area, two roof top tennis courts, and social room. One garage space is included. Laundry is located just outside the unit. Water, cable/internet are included. Walk to the waterfront, restaurants, shopping and theaters. All within minutes away. A short drive to beautiful LIDO BEACH. CALL NOW FOR A SHOWING BEFORE IT'S GONE!

SARASOTA

1111 N GULFSTREAM AVENUE 16C

2 Beds

2 Baths

1,996 Sq.Ft.

$5,000

MLS#: A4650116

RENTED JAN., FEB., MARCH., 2026. This 2nd floor Carlton featuring 2 bedrooms and 2 baths and offers one of the most spectacular views from the screened and glass-enclosed lanai of the lake and golf course that you will find in the entire community. Nicely furnished with a king bed in the master, twins in guest, flat-screen TVs, internet access, very well equipped kitchen, you will want for nothing, one car detached garage, heated pool and tennis courts right outside your door; golf membership transfers for $250 if desired. Stoneybrook is a gated community with impressive clubhouse featuring one of Sarasota's finest restaurants, plus fitness center, several heated pools, and an 18 hole par 72 premier golf course recently refurbished, and har-tru tennis courts also refurbished. All this and minutes from world-famous Siesta Key sugar sandy beaches, shops & restaurants. CALL FOR OFF-SEASON RATES

SARASOTA

8911 VERANDA WAY 222

2 Beds

2 Baths

1,555 Sq.Ft.

$5,000

MLS#: A3984795

Variable rent based on season

SARASOTA

6157 MIDNIGHT PASS ROAD D32

2 Beds

2 Baths

1,332 Sq.Ft.

$5,000

MLS#: A4544448

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