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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

4,571

# of Listings

2

Avg # of Bedrooms

$484

Avg. $ / Sq.Ft.

$870,849

Med. List Price

Browse Downtown Sarasota Real Estate Listings

All listings

$250,000 - $500,000

4571 Properties Found. Page 237 of 305.

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, and your own private pool—this turnkey furnished 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

**ANNUAL 3/3/3 plus OFFICE/DEN AVAILABLE ***GORGEOUS home for rent in Shoreview Lakewood Ranch area**Steps away from the dog park and luxury resort style clubhouse! Boasting BEAUTIFUL finishing touches, wood grain tile throughout, garden tub in the master bath, recess lighting, granite countertops, modern ceiling fans, and zero corner sliding glass doors and more, this home has it all!!. Nestled in the sought after Waterside community, with a farmers market every Sunday, waterfront dining, shopping, kayaking, festivals, and nature trails in very close proximity!! You will never have to go far for entertainment or to just enjoy the luxurious Florida lifestyle! One small pet ok with owner approval Home will be offered unfurnished.

SARASOTA

817 SEASCAPE PLACE

3 Beds

3 Baths

3,377 Sq.Ft.

$5,000

MLS#: N6137055

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

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

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

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

Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing, totally renovated 1 bedroom has 2 full baths, and is conveniently located on the ground floor close to your assigned parking space. Owner has an air mattress available for guests, a new coffee table, an electric fireplace, new shower heads, a portable electric grill, bikes, beach chairs, and a new 10X10 beach canopy. An open kitchen and remodeled bathrooms are some more of the perks in this waterfront unit. Sit on your lanai and watch the boats go by as you sip your morning coffee. Amenities include direct beach access to Siesta Key beach, the #1 beach in the USA, community pool and spa, sauna, fitness, shuffleboard and walking distance to shops, restaurants and entertainment. Close proximity to the Stickney Point bridge enables easy access on and off the Key. This is a 55+ community which means one renter in the party must be over 55 years of age. No pets and no smoking please. 1 car reserved parking space.

SARASOTA

1257 S PORTOFINO DRIVE 36

1 Beds

2 Baths

865 Sq.Ft.

$5,000

MLS#: A4125928

Siesta Dreams at Casa Mar – 1BR/1BA Beachfront Condo with Resort Amenities
Welcome to Siesta Dreams at Casa Mar, your perfect beach getaway on world-famous Siesta Key! This fully equipped 1-bedroom, 1-bath condo offers everything you need for a relaxing, sun-soaked vacation.
Enjoy exclusive access to the resort’s private stretch of Siesta Key Beach, where lounge chairs await on the cool, quartz-white sand. Need a break from the waves? Take a dip in one of two sparkling pools on the property. Feeling active? Enjoy tennis, pickleball, or shuffleboard—all just steps from your door.
Inside, the condo is thoughtfully appointed with your comfort in mind. The king-size bed in the bedroom and a sleeper sofa in the living area accommodate up to 4 guests comfortably. Whether you're enjoying a morning coffee on the patio or preparing a meal in the fully stocked kitchen, you’ll feel right at home.
Surrounded by tropical landscaping and a laid-back coastal vibe, Casa Mar is the kind of place that makes it hard to leave.

SARASOTA

6006 MIDNIGHT PASS ROAD 16

1 Beds

1 Baths

708 Sq.Ft.

$5,000

MLS#: A4659596

Listing reflects off-season rate. Available peak season months: March 2026, April 2026. Introducing your dream beachfront getaway in Siesta Key, Florida or as we like to call it... 2 Tickets to Paradise! This stunning 2-bedroom, 2-bathroom beachfront condo offers the perfect blend of luxury and relaxation. With direct beach access and tranquil views of the garden and ocean, it's the perfect spot to unwind. Step inside to discover a large kitchen, ideal for preparing meals and entertaining. The primary suite offers complete relaxation with a comfortable king-sized bed, a cozy spot to read a good book, and a large ensuite bathroom with a walk-in shower. Up to bringing friends or family? There's plenty of room in the guest bedroom, offering two double beds and their own access to the guest bathroom. Did we mention paradise includes your own wet bar and wine fridge!? Pour yourself a drink of your choice, walk over to watch the exquisite sunsets in the enclosed patio, and don't forget to open the sliding glass windows to let the cool ocean breeze in! Enjoy Gulf & Bay’s impressive amenities including 3 heated pools, 8 tennis courts, a fitness center, BBQ areas, and private access to Siesta Key Beach! You've waited so long, and now the wait is over, you've got 2 tickets to paradise!

SARASOTA

5760 MIDNIGHT PASS ROAD 208D

2 Beds

2 Baths

1,361 Sq.Ft.

$5,000

MLS#: A4550517

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