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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
4,296
# of Listings
2
Avg # of Bedrooms
$496
Avg. $ / Sq.Ft.
$879,900
Med. List Price

Browse Downtown Sarasota Real Estate Listings

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4296 Properties Found. Page 213 of 287.

Available now. Lovely pool home with canal water frontage located in Siesta Key's peaceful and secluded neighborhood of Palm Island. Completely renovated with new kitchen, bathrooms, and floor coverings throughout this island retreat. Walk four blocks to the crystal sands of world famous Siesta Beach, and just a short walk to the Village. Beautiful backyard with spacious patio, heated swimming pool/spa and boat dock with lift.
#A4652924

SARASOTA

306 ISLAND CIRCLE

4 Beds

3 Baths

2,728 Sq.Ft.

$7,500

MLS#: A4652924

Winter 2026 rental two month minimum January and February or three month January-March. Charming Sarasota Retreat with pool and putting green in Gulf Gate Welcome to your perfect Sarasota getaway! Nestled in the desirable Gulf Gate neighborhood, 2921 Captiva Dr. offers a relaxing retreat just minutes from world-famous Siesta Key Beach. This beautifully appointed vacation rental features a private pool, a spacious open floor plan, and all the comforts of home, making it an ideal spot for families, couples, or friends looking to unwind in paradise. Step inside to find a bright and airy living space with stylish coastal décor, a fully equipped kitchen, and comfortable bedrooms designed for restful nights. Outside, the lush backyard oasis invites you to soak up the Florida sunshine—lounge by the sparkling heated pool, enjoy alfresco dining on the patio, or fire up the grill for a fun evening under the stars. Located in the heart of Gulf Gate, you’ll be just minutes from Sarasota’s best attractions, including Siesta Key’s powdery sand beaches, charming local shops, and an array of delicious restaurants. Whether you’re looking to explore vibrant downtown Sarasota, hit the nearby golf courses, or simply relax by the pool, this vacation home is the perfect home base for your stay. Book your escape today and experience the best of Sarasota in this delightful Gulf Gate retreat! Heated pool. and putting green. Available for seasonal rental January 15- March 25
#A4641886

SARASOTA

2921 CAPTIVA DRIVE

4 Beds

2 Baths

1,905 Sq.Ft.

$7,500

MLS#: A4641886

Welcome to The Castaway Cottage, your own private coastal retreat close to Downtown Sarasota and area beaches. There's room for the whole crew in this 3 bedroom 2 bathroom pool home with designer upgrades and beachy motif. Located just steps from the Ed Smith Stadium where the Orioles host their Spring Training games the house is quiet, comfortable and centrally located to all of the best Sarasota Amenities. The property is fully fenced, pet friendly and is being offered turnkey furnished. Castaway Cottage is just 1.2 Miles from Main St Sarasota! The Castaway Cottage offers the ideal floor plan for families and large (or small) groups on vacation, working remotely, or house hunting for any length of time. The space sets up as follows: The front door opens into a large living room with immediate views of the sparkling newly surfaced pebble pool. Seating in the living room is provided for up to 10 people including two swivel chairs, a three seater leather queen sleeper sofa, a retro chair with ottoman and a hightop table with 4 chairs (which doubles as the dining table). The room features a 60 inch mounted flat screen TV with access to complimentary streaming services and lightning fast internet speed. Vaulted ceilings and wall to wall sliders make the space feel light, bright and open and a pass through into the kitchen with two bar stools allows everyone to take part in the conversation. The living room also offers a dry bar with barware and boardgames. The Master bedroom occupies its own wing of the house and includes a large walk in closet, a well appointed en suite bathroom, a work station, and a 60" flat screen TV. The 2nd bedroom offers two twin beds while the third bedroom offers a queen bed with pool access via sliding glass doors. A shared bathroom is located between these two bedrooms. The kitchen is well appointed and features new quartz countertops with a lagoon blue backsplash, a work station looking out onto the pool and backyard and two bar stools overlooking the living room. Access to the pool can be had from the kitchen, the living room sliders or the 2nd bedroom sliders. The lanai offers seating for up to 10 people including a high top dining table (seating for 4), 4 club chairs, and 2 lounge chairs. The entire pool area is screened and offers a Webber 2-burner grill and a 70qt Coleman cooler which doubles as an extra seat if needed. Outside of the pool area you will find a 2nd lanai which is uncovered and offers chaise lounges for up to 3 guests. The backyard is fully fenced and features an elevated seating area with conversation Adirondack chairs and table. This area is conveniently covered by a large shade sail to block afternoon sun and can be lit up at night with LED string lights. Guests will be provided with a unique access code to utilize throughout their stay on the front door keypad. This eliminates the need for guests to keep track of keys.
#A4510442

SARASOTA

1019 SNEAD AVENUE

3 Beds

2 Baths

1,295 Sq.Ft.

$7,500

MLS#: A4510442

Fantastic Beach to Bay community on south Siesta Key! Beach side cabanas, and bayside Boat/Fishing docks. Amazing waterfront views from this 2nd floor 2BR/2BA turnkey furnished condo. Grill areas and pools on both bay side and gulf side. Available anytime except for March 2026. 2025 rates are $1500/wk, 2026 Season rates are $7500/mo (one month minimum during season).
#A4662156

SARASOTA

8635 MIDNIGHT PASS ROAD 206C

2 Beds

2 Baths

1,222 Sq.Ft.

$7,500

MLS#: A4662156

BOOKED JAN/FEB 2026, AVAILABLE MARCH/APRIL 2026. This beautiful UPDATED TURNKEY FURNISHED 3 bedroom/2-bathroom pool home is located in the sought-after area of Gulf Gate, some of the features in this immaculate vacation home includes high-end stainless-steel appliances, wood cabinets, Granite kitchen counters, Plantation Shutters, Master Bathroom with marble counters, Dual Sinks and Walk-in Closet. 3rd bedroom is also used as a Den/Study with a convertible queen size sleeper sofa. Relax, swim or lay in the sun on the newly replaced screen enclosure and pool deck. All this is conveniently located near the Gulf Gate Village, walking distance to nearby restaurants and shopping and a short drive or bike ride to the beautiful world-famous beaches of Siesta Key. Additionally, Sarasota offers so many attractions, Nightlife, Entertainment, Festivals, Museums, Golfing, Sailing, Jet Skiing, Sunset Dinner Cruises from Sarasota Bay, and just a short drive to Sarasota Airport.
#A4549439

SARASOTA

6758 S LOCKWOOD RIDGE ROAD

3 Beds

2 Baths

1,439 Sq.Ft.

$7,500

MLS#: A4549439

No damage from Hurricane Helene or Milton! Available for seasonal and annual rental 2025, call agent for pricing. Discover the epitome of waterfront living in this exquisite 3-bedroom, 2-bathroom home located in Sarasota, Florida. Set on over a quarter-acre of prime land, this beautiful residence features a spacious 1,995 square foot open floor plan that leads to your private pool, ideal for entertaining and soaking in stunning canal views. Boating enthusiasts will appreciate the convenient boat lift, offering direct access to the serene canal waters leading you directly into the Bay. The thoughtfully designed layout harmoniously integrates indoor and outdoor living spaces, allowing you to fully embrace the picturesque surroundings. Experience the coastal lifestyle with this canal-front home, which is not just a residence but a true waterfront retreat. You’re within close proximity to Siesta Key Village, award winning beaches, Gulf Gate Shopping Mall, Publix, Costco and so much more!
#A4609574

SARASOTA

1649 STANFORD LANE

3 Beds

2 Baths

3,092 Sq.Ft.

$7,500

MLS#: A4609574

Water, Water, Water Views! RENT THIS UNFURNISHED CONDO WITH Million-dollar views! 6th and 7th floors of Water and Sunset Views. Rarely available 3-bedroom 3 bath penthouse. One of two penthouses in Harbour House West. Stunning unobstructed panoramic views of Sarasota Bay overlooking the Ringling Bridge. Beautiful Sunsets and Ringling Bridge lights at Night what a treat. Upgraded Kitchen has solid cabinetry, large pantry and stainless appliances. Surround sound for your listening pleasure. Freshly painted. 3rd bedroom with its own bathroom is located by leading up the Spiral staircase. Great views from every bedroom and living room. Views will never seize to amaze you. Live the life and enjoy all that Waterfront living has to offer. Bridge leads to St Armands Circle, Lido beach. Enjoy the shopping and eateries. Short distance to the Van Wezel, library, Selby Gardens, farmers market and Marina Jacks. Your own dedicated parking space and guest parking for your convenience. Fitness room and Day dock included. Call today for your own private showing. Easy to show. Owner is willing to do Lease option purchase. Rent includes water, sewer and trash pickup. Per HOA rules tenants are not allowed pets.
#A4652571

SARASOTA

226 GOLDEN GATE POINT 63

3 Beds

3 Baths

1,778 Sq.Ft.

$7,500

MLS#: A4652571

Back on the RENTAL market, after months of post hurricane rehab. Some interior and exterior improvements! Welcome to Heron's Aqua Breeze! This 3-bedroom 2 1/2 bath canal home with pool is back on the short-term rental market and located just 1 and as half miles to world famous SIESTA KEY BEACH! Spacious and well appointed, this home is equipped for a memory making vacation in a tropical paradise, The kitchen was recently remodeled with beautiful cabinetry and new stone counters and has been stocked with everything you might need for a romantic dinner or fun night with the family. Forget about Starbucks, owners have designated a coffee bar area complete with space and specialty appliances to kick start your mornings to lounge on the large private lanai overlooking the pool and canal with your perfect cup of coffee. Tons of natural light spill into every room and dining room looks right out to the canal. There is a large living room with lots of seating on the new and large luxury leather sectional, but also another gathering room to watch TV, read a book, or eat your eggs while watching the morning news. Owners have also appointed an office area with desk for those guests who have to do a little work. The generous sized primary bedroom has a large walk-in closet and has that Tommy Bahama feel. Two guest bedrooms are in the opposite side of the house, along with a bathroom with walk in and accessible shower. One of those guestrooms has a half bath as well. This neighborhood is the closest you get to Siesta Key. Four bikes are provided for guests, but BRING YOUR OWN BOAT, as this home has deep water docking outside your back door and it only takes 4 minutes to get to the Gulf of Mexico! Gorgeous view in the breezy back yard as it is lined with multimillion dollar estates that you will enjoy looking at while you are sipping your late afternoon libation. Go ahead and fire up that gas grill too, because sometimes you just want to stay in tank tops and shorts while enjoying the perfect temperatures Sarasota has to offer. This location is near great restaurants, shopping, and grocery/drug stores. Exterior of home has a driveway in front of a 2 car garage and circular drive space. When you are a guest here, you can't miss Sarasota's exceptional arts and theatre happenings, along with the very hyped about bustling downtown area, and thriving Main Street, located just 5-7 miles away. This property is a slice of heaven, feeling very private, and very casual. Owner will also consider an annual.
#A4624047

SARASOTA

1714 MEADOWOOD STREET

3 Beds

2 Baths

2,831 Sq.Ft.

$7,500

MLS#: A4624047

Three beds +office, 2 bath vacation rental home in Tahiti Park. Tastefully decorated, flat screen TV's and Wi Fi throughout. This wonderful home has all you need for the perfect vacation retreat. The master bedroom features a king-sized bed, walk in closet, dual sinks in the bath, the guest bedrooms both have queen beds and there is an office that opens onto the spacious screened Lanai and pool area. The large open kitchen is well appointed with all you need. The lap pool is perfect for those wanting to stay in shape. This lushly landscaped home has an "old Florida" feel to it and is very private. Available for seasonal rentals all months except MARCH, also available for longer stays. Small dog OK with owner approval, sorry, no cats due to allergies. ($150 Cap on utilities per month) Booked January, February, and March and April 2025
#A4145643

SARASOTA

1125 HAMPTON ROAD

3 Beds

2 Baths

2,888 Sq.Ft.

$7,500

MLS#: A4145643

Price reduced
Literally steps to the Beach! Just bring your luggage and you can start enjoying this fantastic 2 Bedroom with 2 Bathroom Seasonal Rental (4 month minimum). Fully Furnished, all Utilities included, Bi-Monthly Cleaning Service, and 6th Floor Unit with stunning Panoramic Views of the Gulf of Mexico and Lido Beach from all Windows and Bedrooms. With multiple Glass Sliders and an Open Floor Plan, the main Living Space feels Light and Bright. The separate Dining Room and Pass-through to the Kitchen are perfect for entertaining friends and family. The large Master Suite has a King Bed with En-Suite Bathroom with Jetted Tub and Shower, a Ceiling Fan, and a Walk-in Closet with Custom Shelving. The 2nd Bedroom has a Queen Bed, Ceiling Fan, and Double Closet. The white and blue themed Hall Bathroom has a Glass Enclosed Shower. The Resort like amenities at St Armand’s Tower South include On-Site Management, a Heated Pool, a Club Room with Full Kitchen, a Fitness Room, and Outdoor Gardens with a Grill. This Rental also features a covered Parking Spot, a 40 Ft Balcony with Patio Furniture for marveling at the breathtaking Sunrises and Sunsets, and plenty of Beach Accessories. St Armand’s Circle is just minutes away with its World Class Shopping, Dining, and Entertainment. Drive over the John Ringling Causeway to Downtown Sarasota and your options are endless. Call today to schedule a viewing. Application required $75/Person 18 years and older. Sorry no pets allowed.
#TB8424965

SARASOTA

101 BENJAMIN FRANKLIN DRIVE 61

2 Beds

2 Baths

1,275 Sq.Ft.

$7,500

MLS#: TB8424965

One or more photo(s) has been virtually staged. Annual unfurnished rental in sought-after Bayso Sarasota luxury complex with gorgeous views from every window. You will love this light and bright two-bedroom plus den, three-bath home. As you enter the condominium, your eyes will be drawn to the floor-to-ceiling windows and sliders overlooking the bayfront and the city. The interior space is well defined and offers a gorgeous designer kitchen with stainless appliances, European cabinetry, a center island and quartz countertops. Just off the kitchen is the laundry room with tons of storage. The main living area has 10-foot ceilings and sliders that open to a 10-foot deep terrace with glass railings that showcase the stunning views. The primary bedroom has stunning views, ample room for a king bed, two closets and a spa-like bath. The guest bedroom has equally stunning views, great closet space and a luxurious bath. The den can be used as an office or combination office/guest flex space. The Bayso community offers a state-of-the-art fitness room with a movement studio for personal and group classes, and a business center on the first level. The fifth floor is where you will find the gorgeous heated pool and spa, the outdoor grilling area, dog park and entertainment area. You will have access to a climatized storage area as well and one conveniently located parking space. Just down Quay Commons you will find the new Ocean Prime restaurant for fine dining as well as The Bay Sarasota with 53 acres for recreation, biking, kayaking and yoga.
#A4671602

SARASOTA

301 QUAY COMMON 1603

2 Beds

3 Baths

2,011 Sq.Ft.

$7,500

MLS#: A4671602

STUNNING BAY VIEWS! This 3 bedroom condo features some of the best bay views in this community. Two KING ensuite bedrooms with baths and an additional guest bath. There is a small 3rd bedroom with two twins, perfect for visiting grandchildren. Boat slips are available on a first come first served basis and is less than $200. Additionally, there are three tennis courts, a kayak launch, fishing pier, shuffleboard courts, pool with hot tub, and a clubhouse. This is a perfect sized community with just two secure elevator entry 6 floor buildings and each unit having a private garage. Light pours into this well-appointed unit with tons of sunlight from almost every window and almost 2000 feet living space. There is so much space to be together or apart with two separate living areas with huge tv's too! Private beach access is just across the street. Free Siesta Key beach trolley pick up and drop off is located right near community entrance and runs 8 AM to 10 PM every day of the week and to 11 PM on Fridays and Saturdays. Three months minimum. Small dog will be considered. This is the first time this property has been offered as a seasonal rental, and perhaps your lucky day!
#A4619765

SARASOTA

8735 MIDNIGHT PASS ROAD 107B

3 Beds

3 Baths

1,969 Sq.Ft.

$7,495

MLS#: A4619765

Indulge in the ultimate coastal lifestyle with this charming 2-bedroom, 2-bathroom first-level condo in the heart of Gulf & Bay Club Bayside on Siesta Key, Florida. As you enter, the coastal vibes welcome you into a thoughtfully designed space adorned with beach-inspired decor and sunlit interiors. Step through the sliding glass doors onto your private screened-in lanai, where the gentle breezes and tropical surroundings invite you to unwind and enjoy the outdoor charm. The well-equipped kitchen features modern appliances and a breakfast bar, perfect for casual gatherings with friends and family. The primary bedroom offers a true escape with sliding glass doors to the lanai, a king-size bed, a TV and an attached bathroom that will make you feel as if you are at the spa! There are two vanities and a stunning tiled walk-in shower. The second bedroom has a king-size bed, plenty of closet space and a TV. The second bathroom has an updated vanity, with a walk-in shower. Gulf & Bay Club Bayside offers resort-style amenities, including pools and tennis courts, all set against the backdrop of beautifully landscaped grounds. With easy access to the pristine beaches of Siesta Key and the vibrant local culture, this first-level condo captures the essence of coastal living. Immerse yourself in the relaxed elegance of this Gulf & Bay Club Bayside residence, where every day feels like a beachside getaway. **Taxes and fees not included.
#A4592999

SARASOTA

1338 SIESTA BAYSIDE DRIVE 1338-C

2 Beds

2 Baths

1,280 Sq.Ft.

$7,400

MLS#: A4592999

Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Experience the ultimate beach getaway at "Carefree Coconut," a charming second-floor corner unit located in the heart of Siesta Key's welcoming Vista Hermosa community. True to its Spanish name, "Beautiful View," this community offers a delightful escape, blending old Florida charm with modern comforts. Step inside to discover a bright and airy space, filled with natural light, featuring a screened balcony with comfortable seating and a remodeled kitchen ideal for entertaining or for the chef in your family. The property includes a primary bedroom with a comfortable King-sized bed and a guest bedroom with a Double bed and a Twin bed with a trundle, ensuring restful nights. The Vista Hermosa community itself provides fantastic resort-style amenities, including a refreshing heated pool, fun shuffleboard courts, a convenient gas grill with picnic tables, and a clubhouse featuring a kitchen – perfect for socializing and making new memories! Your prime location means you're just moments from the lively South Village, a hub of locally-owned restaurants, charming cafes, vibrant bars, and unique boutiques. A leisurely ten-minute walk brings you to Siesta Key’s stunning Crescent Beach, famous for collecting seashells and those world-renowned Gulf sunsets. For an unforgettable underwater experience, the unique landmark Point of Rocks is also nearby, a snorkeler's paradise teeming with tropical fish and vibrant coral reefs! For larger groups, consider booking unit 308C, also managed by Ascendia Group, which can accommodate an additional 4 guests, allowing your whole family to enjoy this incredible destination together. Come discover why "Carefree Coconut" is the perfect spot for your next Siesta Key escape!
#A4578083

SARASOTA

116 VISTA HERMOSA CIRCLE 210C

2 Beds

2 Baths

980 Sq.Ft.

$7,200

MLS#: A4578083

Relax in the spacious living area or enjoy a glass of wine on the lanai.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.
#A4589578

SARASOTA

1351 SIESTA BAYSIDE DRIVE 1351-D

1 Beds

1 Baths

959 Sq.Ft.

$7,200

MLS#: A4589578

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