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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

3,931

# of Listings

2

Avg # of Bedrooms

$489

Avg. $ / Sq.Ft.

$878,441

Med. List Price

Browse Downtown Sarasota Real Estate Listings

All listings

$250,000 - $500,000

3931 Properties Found. Page 193 of 263.

New on site 3 days ago

Fully Furnished seasonal country home on 5 acres with private stocked pond. If you want to feel an abundance of nature, wildlife and calm but still close to Sarasota and I75 book your flight tickets NOW. This home has all new furnishings, 3 bedrooms, office with desk and door for privacy, formal dinning, living room and family room to enjoy. Almost all rooms have a pool view, some have a distance pond and tweed view.
come relax and feel the calm with sunset views for the winter in privacy. The cottage in the back does have a full time renter, the only thing you share is the front driveway.

SARASOTA

1950 BERN CREEK LOOP

3 Beds

2 Baths

3,086 Sq.Ft.

$6,500

MLS#: A4669098

Immaculate End Unit in the Marlin building, Ready for you to Enjoy through January 2026 and April 2026 through year-end 2026! Stunning all the way, Great Location in the complex, close to the pool, clubhouse, spa, sauna, 2 bedroom 2 full baths, enclosed lanai overlooking the canal, steps to Deeded beach access through Crescent Arms, for your pleasure daytime or sunset time! Siesta Harbor offers a heated pool, outdoor jacuzzi, indoor sauna, fitness room, newly surfaced shuffleboard court, great clubhouse to enjoy the beautifully decorated main room, kitchen with barbecue area, library, Siesta Harbor is located directly on the main intracoastal waterway and has a dock with seating for your enjoyment to watch the boats going by, a little fishing or relaxing! The Trolley and Scat right at our doorstep and walk to shops, restaurants beach, all for you to enjoy in Paradise! Open Floor Plan, enclosed lanai, dining area open to the living room, lots of windows since this is an end unit. Beautiful water views of the canal. Two bedroom, two bathroom and beautiful flooring throughout. Come to our Paradise! Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This South facing renovated condo is in the building closest to the pool, and you have your own assigned parking space. 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, voted the number One beach in the USA, community pool and spa, sauna, fitness room, newly surfaced shuffleboard court 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.

SARASOTA

1250 N PORTOFINO DRIVE M301

2 Beds

2 Baths

1,123 Sq.Ft.

$6,500

MLS#: A4478353

Available January to April 1, 2026! Beautiful two bedroom, two bath spacious condo. Furnished lanai with view of the Harbor and the Intracoastal Waterway - rarely available! Fifty-five+ community. Easy walk to deeded beach access to Siesta Key, the Number One Beach in the Country! Heated Outdoor Pool and Spa, Saunas, Modern Clubhouse, Patio Seating Area on the canal and our own Siesta Harbor Fishing Pier. Boat slips available by applying to the office. The trolley stop is at the entrance of the complex. Walk to restaurants and bars, easy on and off the key! You Deserve Paradise!

SARASOTA

1250 N PORTOFINO DRIVE 102MAR

2 Beds

2 Baths

929 Sq.Ft.

$6,500

MLS#: A4522405

THE PERFECT CONDOMINIUM RIGHT IN THE HEART OF DOWNTOWN SARASOTA. Charming two bedroom, two bath condominium, all new laminate wood flooring throughout, offering the ideal layout which guarantees privacy for both bedrooms. King bed in the main bedroom and Queen bed in the guest room. The kitchen has granite counters and solid wood cabinets. Convenience blends with elegant design throughout the unit, the high ceilings, the open floor plan, and a terrace accessible from the master suite and living room. The location combines luxury and urban lifestyle; across the street from the library, walk to theaters, shops, restaurants and our magnificent Sarasota Bayfront. ONE HUNDRED CENTRAL has a 24/7 concierge service in this very secure building. Amenities are heated pool and spa, outdoor grill/entertaining area, a gathering room with a fireplace and caterer's kitchen, library room and a state of the art fitness center. SEASON IS DECEMBER-APRIL AT $6500 A MONTH, OFF SEASON IS MAY-NOVEMBER AT $4200 A MONTH. DOWNTOWN SARASOTA, VACATION RENTAL, LUXURY.

SARASOTA

100 CENTRAL AVENUE 620

2 Beds

2 Baths

1,115 Sq.Ft.

$6,500

MLS#: A4406251

Annual unfurnished townhouse available for lease in downtown Sarasota, right on the bay! The townhouse combines gorgeous water views with downtown convenience and in the beautiful community of Marina Suites at end of Blvd of the Arts. The 16,000 lb boat lift can hold a boat up to 40ft to 44ft and is available for an additional $1000 per month. The home features beautiful maple wood engineered flooring, a newly remodeled kitchen with Sub-Zero and Wolf appliances, and marble and travertine throughout. An open circular staircase from the ground to third floor is capped with a skylight that brings light into the entire space. The top level includes the main with luxurious spa-like en-suite bath, a guest bedroom with an en-suite bath and space in between for an office. The middle level features an open great room with a built-in bar ideal for entertaining guests, an open kitchen and dining room, all with views of the water. The first level includes a guest suite with room for office/living space with bedroom, private patio and bath—square footage on this floor is not included in listed square footage. A laundry room off the kitchen leads to a two-car garage with plenty of storage above. Community amenities include resort-style heated pools, tennis, exercise areas, boat/kayak docks and a 24-hour staffed security gatehouse. Just .9 miles to Main Street, three miles to St. Armands and 3.5 miles to Lido Beach. Go to the Hyatt, The Van Wezel, the waterfront park, the Ritz and more.

SARASOTA

922 BLVD OF THE ARTS 922

3 Beds

3 Baths

1,907 Sq.Ft.

$6,500

MLS#: A4657611

Looking for a sunny escape from the winter chill? Welcome to your fully furnished seasonal rental in the sought-after Turtle Bay community on Siesta Key, just minutes from the award-winning sand of Siesta Key Beach. This beautifully updated second-floor 2-bedroom, 2-bath condo offers sweeping views of Sarasota Bay, high-quality finishes, and resort-style amenities, ideal for a 3-month seasonal stay. The unit comfortably sleeps six, making it perfect for families or groups seeking a relaxing coastal getaway. Enjoy 1,357 sq ft of stylish coastal living with luxury vinyl flooring throughout, a modern kitchen featuring granite countertops, stainless steel appliances, and ample cabinet space. Both bathrooms are fully renovated with walk-in showers and updated fixtures. A private in-unit laundry closet adds everyday convenience. Step out to the screened lanai and take in the bay breeze and peaceful water views, your own slice of Siesta Key serenity. The spacious primary suite includes a king-size bed, en-suite bath, and generous closet space, while the guest bedroom is perfect for visitors or additional flexibility. This condo is truly vacation ready, complete with beach chairs, umbrellas, and everything you need for a relaxing beach vacation. Plus, enjoy private beach access just a short walk away via the Tortuga community across the street. The Siesta Key Trolley stop is conveniently located nearby, providing easy access to the Public Beach and Siesta Key Village, where you can enjoy restaurants, souvenir shops, ice cream treats, and the lively live music scene that sets the island’s vibe. The Turtle Bay community offers residents access to an in-ground swimming pool, relaxing jacuzzi, and gas BBQ grills, perfect for enjoying the Florida lifestyle to the fullest. Boat slips are also available on a first-come, first-served basis for a nominal fee, perfect for boaters eager to enjoy direct access to Little Sarasota Bay. The building also features elevators for easy access. Garage storage is available but is not accessible for vehicle parking. AVAILABLE IMMEDIATELY from October 2025 - June 2026.

SARASOTA

8735 MIDNIGHT PASS ROAD 206b

2 Beds

2 Baths

1,472 Sq.Ft.

$6,500

MLS#: A4667149

#A4599307

SARASOTA

9393 MIDNIGHT PASS ROAD 302

2 Beds

2 Baths

1,128 Sq.Ft.

$6,500

MLS#: A4599307

New on site 3 days ago

LOVELY single family home available to rent in the desirable community of Colonial Oaks. This turnkey furnished home is located on a quiet cul-de-sac, has 3 bedrooms, 2 bathrooms, kitchen/family room combination, dining room, bonus game room, split bedrooms, 1,844 square feet and plenty of room to spread out. The kitchen has lots of cabinet and counter space for cooking and preparing plus bar seating. The primary bedroom has a king sized bed, walk in closet and an ensuite bathroom with walk in shower and double sinks. The two guest bedrooms also have king sized beds. The guest bathroom has a tub/shower combination. The home has a fantastic lanai with seating, outdoor television, sink/wet bar, fire pit with seating area, a BBQ grill and saltwater heated pool and hot tub. This home is not one to miss. Colonial Oaks is located close to I75, University Town Center, Pinecraft, Siesta Key Beach and all that Sarasota has for fun and entertainment. Available now through January 2026 then open for March 2026 and on for single or multiple month bookings. Guest to also pays state/local tax, booking fee and damage deposit. Sorry no pets allowed.

SARASOTA

2246 CORK OAK STREET W

3 Beds

2 Baths

1,884 Sq.Ft.

$6,500

MLS#: A4669343

Gorgeous Canal View Condo now available on Siesta Key as an annual rental. Rent for the remainder of 2025 through the Winter Season until December 2026 and work from home on your walk-out lanai watching the deep water boats on the Intracoastal Waterway. Incredible View of the Intracoastal Waterway, Beautiful two bedroom, two bath spacious first floor walk-out condo with lots of natural light. Completely remodeled and fully renovated in March 2023! One month minimum, Fifty-five+ community. Crescent Arms beach access to Siesta Key Beach directly across the street, the Number One Beach in the Country! Heated Outdoor Pool and Spa, Sauna, Modern Clubhouse, Activities all Season, Patio Seating Area on the canal and our own Siesta Harbor Fishing Pier. Boat slips available by applying to the office. The trolley stop is at the entrance of the complex. Walk to restaurants and bars, easy on and off the key! You Deserve Paradise!

SARASOTA

1350 N PORTOFINO DRIVE 108TAR

2 Beds

2 Baths

86 Sq.Ft.

$6,500

MLS#: A4581886

#A4640012

SARASOTA

800 BENJAMIN FRANKLIN DRIVE 608

2 Beds

2 Baths

1,590 Sq.Ft.

$6,450

MLS#: A4640012

This 2 bedroom, 2 bath condo in this popular 55+ community, is conveniently located on the ground floor next to the club house and swimming pool, and features new appliances, granite counter tops and ceramic flooring.
Queen size bed in the Master with a walk in closet plus a full wall length closet. The guest bedroom has 2 single beds that can be combined to make a King. Updated bathrooms include a guest bath with a tub/shower combination.
The complex is surrounded by the Intracoastal Waterway with boat access to the Bay. Boat slips can be rented for a nominal fee. Enjoy your morning coffee on the large Lanai overlooking the boats in the Harbor. There is 1 assigned carport and ample visitor parking.
Siesta Harbor has a large saltwater heated pool, spa, fitness center, outside grills and tables, shuffle board courts, boat docks, fishing pier, a large community room with kitchen facilities for parties and a small lending library and pool table to occupy your time on that rare non-sunshine day.
Across the street is Crescent Beach (Siesta Beach) rated #1 beach in America with deeded beach access for Siesta Harbor guests.
Put your toes in the fine quartz sand that stays cool on your feet as you walk along the Gulf of Mexico shoreline. Siesta Key Trolley offers free rides to Turtle Beach or Siesta Village. Siesta Harbor is an over 55 community. No pets allowed. High season rates in effect December through April.

SARASOTA

1250 N PORTOFINO DRIVE 107MAR

2 Beds

2 Baths

1,061 Sq.Ft.

$6,400

MLS#: A4120613

Welcome to your dream coastal retreat at Gulf & Bay Bayside in Siesta Key, Florida! Nestled within this exclusive waterfront community, this exquisite two-bedroom condo offers a perfect blend of luxurious living and breathtaking views.

As you step into this meticulously designed residence, you are greeted by an open-concept living space adorned with tasteful coastal decor. The living area, bathed in natural light, invites you to unwind and relax with its comfortable furnishings, creating a seamless connection between indoor and outdoor living. Slide open the glass doors to reveal a private lanai overlooking the lush landscaping.

The kitchen is a culinary haven, boasting modern appliances, sleek countertops, and ample storage space. Whether you're preparing a gourmet meal or enjoying a casual brunch, the kitchen is as functional as it is aesthetically pleasing.

The two bedrooms are offering a tranquil oasis for rest and relaxation. The primary bedroom, complete with a spa-like ensuite bathroom, provides a sanctuary of comfort utilizing a king-size bed and large TV. The second bedroom has a full-size memory foam bed with a TV, offering privacy and comfort. The living room offers a very comfortable queen size memory foam sleeper sofa complete with the necessary linens.

Gulf & Bay Bayside ensures guests enjoy a resort-style lifestyle with an array of amenities, including a sparkling pool overlooking the bay, a fitness center, and meticulously landscaped grounds. Take a leisurely stroll through the community, enjoying the tropical flora and the proximity to Siesta Key's famous white sandy beaches.

**Taxes and fees not included.

SARASOTA

1326 SIESTA BAYSIDE DRIVE 1326-D

2 Beds

2 Baths

959 Sq.Ft.

$6,300

MLS#: A4593068

RARE OPPORTUNITY to RENT THE PENTHOUSE. 3 BEDS/2.5 BATHS full size washer/dryer and a roof top deck with panoramic views available September 2025 stay for a year, 2 or 3+ owner wants this beautiful turnkey home with a BOAT DOCK (no lift yet)RENTED LONG TERM. Owner open to lift discussion. You will enjoy Penthouse end unit in Boca Siesta is located in the heart of Siesta Key the #1 Beach in the U.S.! This gem can be rented Annually. This turnkey unit is fully furnished. Boasting endless amounts of natural light from nearly every window. Impeccable views of the Intracoastal waterway. The spiral staircase in the Florida room leads to the roof top deck where you can enjoy a glass of Champagne while basking in the roof top jacuzzi watching the sunset over the Gulf. After a long day at the beach kick back with friends and family around the secluded outdoor fire pit. 3 outdoor grills are readily available to cook up your fresh catch. Luxurious Master Suite with separate shower and Jacuzzi tub. Recently updated gourmet kitchen w/ maple cabinets and granite counters w/ breakfast bar comes fully stocked for your enjoyment. If you to get some work done there are three working spaces in the unit. Clubhouse with tennis court and pool overlooking the intracoastal. Unit comes with all equipment to enjoy a game of tennis, pool and beach toys. There are two covered parking spaces and plenty of additional parking available for guests. Private pier that can accommodate up to a 25' boat. Deeded beach access directly across the street within short walking distance RARE OPPORTUNITY to RENT THE PENTHOUSE. 3 BEDS/2.5 BATHS full size washer/dryer and a roof top deck with panoramic views available May 1, 2025 stay for a year, 2 or 3+ owner wants this beautiful turnkey home with a BOAT DOCK (no lift yet). Owner open to lift discussion. You will enjoy Penthouse end unit in Boca Siesta is located in the heart of Siesta Key the #1 Beach in the U.S.! This gem can be rented Annually. This turnkey unit is fully furnished. Boasting endless amounts of natural light from nearly every window. Impeccable views of the Intracoastal waterway. The spiral staircase in the Florida room leads to the roof top deck where you can enjoy a glass of Champagne while basking in the roof top jacuzzi watching the sunset over the Gulf. After a long day at the beach kick back with friends and family around the secluded outdoor fire pit. 3 outdoor grills are readily available to cook up your fresh catch. Luxurious Master Suite with separate shower and Jacuzzi tub. Recently updated gourmet kitchen w/ maple cabinets and granite counters w/ breakfast bar comes fully stocked for your enjoyment. If you to get some work done there are three working spaces in the unit. Clubhouse with tennis court and pool overlooking the intracoastal. Unit comes with all equipment to enjoy a game of tennis, pool and beach toys. There are two covered parking spaces and plenty of additional parking available for guests. Private pier that can accommodate up to a 25' boat. Deeded beach access directly across the street within short walking distance.

SARASOTA

5911 MIDNIGHT PASS ROAD 601

3 Beds

2 Baths

2,260 Sq.Ft.

$6,300

MLS#: A4659864

Fully OPEN for 2026 SEASON RESERVATIONS-SARASOTA POOL HOME in CORAL COVE. Just completed newly furnished and UPDATED 3BR, 3BA waterfront pool home is ready for your arrival. RENTAL HOME Available for LEASE. Coastal Living at it's best, WEST OF THE TRAIL!! This amazing home overlooks a saltwater canal with a private dock access for fishing, kayaking and boating in the Sarasota Bay. Dive-In or float in the heated in ground pool. Move-In and enjoy the Florida indoor/outdoor lifestyle. Just completed, a spacious screened lanai with a covered patio and large sunshine area to relax. Inside the home, the great room floor plan opens up the home's living area to capture the views and sunlight throughout. All three bedroom feature queen size beds and are en-suite with full size updated bathrooms. Well equipped Eat-In kitchen. Located in Sarasota, less than four miles to the beautiful #1 rated Siesta Key beaches and village. The Coral Cove neighborhood private 2-acre park is a walk away from the home. The tree lined waterfront park features a boat ramp, day dock, excellent fishing opportunities, and scenic views. This location offers endless opportunities to explore in Sarasota during your stay: Legacy Trail for bicyclists, Marie Selby Botanical Gardens, Ringling Museum, Performing Arts theaters, and Downtown Sarasota. One month minimum stay. Monthly Rates for May through November $3500 and December through April $6250, +13% tax on stays for one to six months. No PETS/ No SMOKING. Don't miss your chance to experience this true coastal rental gem. OPEN FOR 2026 SEASON RESERVATION FOR TWO MONTH OR LONGER STAY.

SARASOTA

1718 CARIBBEAN DRIVE

3 Beds

3 Baths

2,803 Sq.Ft.

$6,250

MLS#: A4643493

Welcome to this charming three-bedroom, two-bath pool home in the desirable Gulf Gate neighborhood. Located on a tree-lined cul-de-sac, this home is conveniently situated just a quarter of a mile from Gulf Gate shops, restaurants, and nightlife, with public transit options nearby.
Enjoy your morning coffee in the sunroom or relax by the screened, private pool. The home features a split floor plan, with the master retreat on one side and two guest bedrooms on the other, offering privacy and comfort. For those who appreciate music, a baby grand piano awaits in the family room.
Please note that the swimming pool is unheated, and one garage space is available, as the owner uses the other for personal storage. The property includes a fully fenced backyard, and one non-shedding pet is welcome with owner approval, with a nonrefundable $300 pet fee.
This home is occupied in the summer and fall months.

SARASOTA

2929 MAYFLOWER STREET

3 Beds

2 Baths

1,694 Sq.Ft.

$6,200

MLS#: A4480615

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