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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

4,276

# of Listings

2

Avg # of Bedrooms

$495

Avg. $ / Sq.Ft.

$878,997

Med. List Price

Browse Downtown Sarasota Real Estate Listings

All listings

$250,000 - $500,000

4276 Properties Found. Page 228 of 286.

Price reduced

Available for season 2026! Available long or short term. As you approach the grand entrance of Heritage Oaks Golf & Country Club, you'll know you are entering a spectacular private community. Once passed the 24-hour secured gates the sense of a fun filled active lifestyle becomes obvious with five heated swimming pools, four lighted Har-Tru tennis courts, state of the are fitness center and offered classes. The elegant recently renovated clubhouse offering fine dining or the 19th Hole Grill Room for a more casual cocktail and meal. Tee times, tennis matches, or an event from the social calendar will keep you busy or simply enjoy natures wildlife within this certified Audubon neighborhood. This is the lifestyle you deserve. It's time to come home to this extremely cozy, finely decorated and well taken care of haven. Choose from the front or rear screened lanais to sit back and enjoy the serene views. The primary bedroom suite has a king size bed, large TV, and walk-in closet and walk-in shower. The second bedroom with a queen size bed is beautifully styled as well and just as comfy as the primary bedroom. The kitchen is well equipped, spacious and open with a counter breakfast bar, bench window dining area, and a bar/coffee drink station. Just a short drive to the beautiful beaches of Siesta Key and downtown Sarasota where you can take in the arts with shows, concerts, ballets, and so much more. Bring your clubs and stay at this very welcoming home within a great community.

SARASOTA

5270 HYLAND HILLS AVENUE 1724

2 Beds

2 Baths

1,530 Sq.Ft.

$4,500

MLS#: A4665879

Charming Bayview Acres Home – Available March 1, 2026
Discover comfort, convenience, and coastal charm in this fully furnished 3-bedroom, 2-bath home located West of the Trail in the highly desirable and non-deed-restricted community of Bayview Acres.
Inside, you’ll appreciate the beautifully renovated kitchen, split floorplan, and thoughtful upgrades throughout. Each bedroom is equipped with a ceiling fan for added comfort, and the impact-rated sliding door opens to a serene screened lanai—an ideal spot to unwind after a day at the beach.
The fully fenced, spacious yard offers plenty of room to enjoy the outdoors, along with extra space to store bikes, beach gear, or anything else you bring along. Situated within the tranquil bird sanctuary of Bayview Acres, the home provides a peaceful, nature-filled setting perfect for relaxation.
This home is designed to make your stay effortless, with all the details that turn a good Siesta Key/Sarasota getaway into a truly memorable experience.
Prime Location: Walk or bike to the beach, shopping, and dining—everything is just minutes away.
Available for Weekly and Monthly Stays.
Take a look—you won’t be disappointed!

SARASOTA

1686 CHAPLINE LANE

3 Beds

2 Baths

1,834 Sq.Ft.

$4,500

MLS#: A4672328

Available month-to-month April 1, 2026 through December 2026, this beautifully updated Gulf Gate Woods pool home is one of Sarasota’s most sought-after retreats. Fully furnished and designed for comfort, this 3-bedroom, 2-bath home sits on an oversized lot in the serene Gulf Gate Woods neighborhood and features updated hurricane doors and windows for added security and peace of mind. The thoughtfully designed split floorplan, ceramic tile throughout, and whole-house water filtration system enhance the home’s luxury feel. Enjoy seamless indoor-outdoor living with a private heated, caged pool accessible directly from the primary suite, guest bedroom, and main living area—perfect for swimming, lounging, or relaxing in an insect-free outdoor oasis. The large backyard is ideal for cookouts and gatherings, while the quiet residential location places you close to everything Sarasota has nearby, from scenic bike rides through Gulf Gate Woods to beautiful beaches just minutes away. Your stay includes Wi-Fi, air conditioning, water, trash removal, laundry, lawn service, and pool maintenance, ensuring a hassle-free experience from start to finish. Now available April 2026 through December 2026—don’t wait, this exceptional home will book quickly. Secure your stay today!

SARASOTA

2410 CASS STREET

3 Beds

2 Baths

2,564 Sq.Ft.

$4,500

MLS#: A4672343

Turnkey Furnished Short Term Rental Available beginning 1/5/26 (Booked 2/1/26 - 3/31/26). Wide open views from this 3rd Floor Condo with Vaulted Ceilings, Engineered Oak Wood Floors Throughout the Main Living areas and views of the 8th Fairway. Don't miss this chance to enjoy the Sunrise Views of the Fairway and across to the Preserve land and Lake. The 2 Bedroom 2 Bath unit Boasts Stainless Steel Appliances, updated shower in the Master Bath with High Quality Shower Head System and a whirlpool tub with shower in the Guest bathroom. Stylish Paint throughout. Master Bedroom has its own slider out to the lanai and walk in closet. Offered Partially Furnished. Carport for the Owners and lots of guest parking as well. Terraces Condo Group has Recently New tile roofs, Modernized Paint colors, community pool and great Pickleball/Tennis court. Community Grills and Gathering Areas make for a social and fun community to be a part of part time or year a round.

SARASOTA

8735 OLDE HICKORY AVENUE 8306

2 Beds

2 Baths

1,373 Sq.Ft.

$4,500

MLS#: A4636624

View the intracoastal by SIESTA KEY from your master bedroom porch having a rest on the reclining chairs. This second floor townhouse is in the perfect location for your stay in SARASOTA and a short distance from a world famous beach. Located by the Stickney Point Bridge this renovated and beautifully decorated townhouse is ready for short term stays of a minimum of one month. Up the stairs to the front door and step into this light filled home, all up to date decorating in neutral tones. There is a guest bathroom on the first floor and an extra single bed for overflow guests. Up to the bedroom level and you will find two bedrooms, the master has a king sized bed and the second bedroom features a queen sized bed. There are two porches for relaxing on, one off the living room and one off the master bedroom. There is a washer and dryer in the unit, and the resort style complex features two swimming pools, one overlooking the bay and tennis courts. SARASOTA, NEAR SIESTA KEY, RENTAL.

SARASOTA

1622 STICKNEY POINT ROAD 22-202

2 Beds

1 Baths

1,334 Sq.Ft.

$4,500

MLS#: A4554533

#A4555248

SARASOTA

500 S WASHINGTON DRIVE 18B

1 Beds

1 Baths

838 Sq.Ft.

$4,500

MLS#: A4555248

This turnkey furnished townhome is available for the 2026 season with a 4 month minimum lease or for longer starting October 1, 2025. Off season or annual rent is negotiable. The home has 2 master suites upstairs, and on the lower level there's a great room, kitchen, dining area and an office/den and 3rd full bath. Located in the gated community of VillageWalk on Palmer Ranch, amenities include clubhouse with meeting/game/party rooms, lending library with internet access, fitness center, 2 heated pools, resort style and lap, 6 har-tru tennis courts, pickleball, miles of walking trails, a cafe, hair salon and gift shop. VillageWalk is just miles away from beaches, shopping and the Interstate.

SARASOTA

5361 ELISEO STREET

3 Beds

3 Baths

2,963 Sq.Ft.

$4,500

MLS#: A4659741

Welcome to your very own slice of paradise in sunny Sarasota, Florida! This beautiful vacation rental is the perfect home away from home if you are seeking an extended stay of three months or more to work or play. With a minimum stay requirement, you'll have plenty of time to soak up the dazzling Gulf Coast and take advantage of everything in this vibrant cultural city.

Situated in the Pinestone of Palmer Ranch community, this lovely two bedroom, two bathroom ground floor condo sleeps 4 comfortably and features all the modern amenities you need for a carefree vacation or work away from home. From the moment you step inside, you'll be greeted by a warm and inviting atmosphere that exudes comfort and relaxation with plenty of room for dining, lounging, and unwinding after a long day in the sun.

Utilities including basic cable TV, Internet/Wifi are included. Pinestone at Palmer Ranch features a clubhouse, lighted junior Olympic size swimming pool, 32 seat movie theater, 1/2 basketball court/Pickleball court, two lighted tennis courts, billiard room, card room, fitness center, library, hot tub/spa, fire pit area with seating and BBQ grills.

Located just a short drive from some of the most stunning beaches on the Gulf Coast, this vacation rental is the ideal place to call home during your stay in Sarasota. Soak up the sun, sand, and surf in one of the many nearby beach destinations, or explore the vibrant culture of the city itself. From world-class dining and shopping to outdoor activities and entertainment, Sarasota has something for everyone.

Although tucked away in a peaceful gated community, Pinestone at Palmer Ranch is 1/2 mile to so many amenities including the Sarasota Square Mall with movie theaters and Costco and around the corner is Target, Publix, shopping, dining. Close by is the Legacy Trail for walking and biking.

Siesta Beach on Siesta Key is only 6.6 miles away over the south bridge where you can experience the soft powdered sugar quartz sand and the aqua blue waters! Siesta Village has local shops and restaurants featuring casual and fine dining. Other beaches to explore include Lido Beach, Ana Maria Island, Holmes Beach and Venice Beach.

Downtown Sarasota is 8.7 miles away with restaurants, visual and performing arts such as the Ringling Museum of Modern Art, Marie Selby Botanical Gardens, Sarasota Opera and the Sarasota Ballet. Just north of downtown is The John and Mable Ringling Museum of Art, Ringling Museum. Explore why Sarasota and the west coast of Florida is referred to as the Cultural Coast!

There is a three month minimum rental period according to the Pinestone at Palmer Ranch Condo Association. There are additional Sarasota sales & tourism tax fees on top of the monthly lease fee if rented less than 6 months.

SARASOTA

8350 WINGATE DRIVE 913

2 Beds

2 Baths

1,226 Sq.Ft.

$4,500

MLS#: A4569199

***WATER VIEWS GALORE**** Breathtaking views of the Sarasota Bay, Fabulous sunsets, and unobstructed views of John Ringling Bridge from every room. TURNKEY FURNISHED Condo on Golden Gate Point. Remodeled 2-bedroom, 2-bathroom waterfront condo has classic style with modern conveniences. Perfect setting for everyday living and special occasions. Whirlpool stainless steel appliances (Refrigerator, Microwave, Dishwasher and Range). Laminate flooring throughout main living area. Chef's delight as well as an entertainer's dream. The gourmet kitchen has custom cabinetry and an oversized quartz island with seating. The primary bedroom features a walk-in closet, a king-sized bed, and an updated primary bathroom. The guest bedroom features a good-sized built-in closet and a queen-size bed. The laundry room comes with a washer, dryer, and lots of storage for your convenience. Most windows have plantation shutters. The main water view windows have motorized blinds. Amenities include a fitness room, Bayfront social area, a day dock with boat slips, guest parking and one premium covered parking for your convenience. Luxurious condo close to downtown Sarasota, Marina Jacks, St. Armand’s Circle, Sarasota Memorial Hospital, Marie Selby Botanical Gardens, Bayfront Park and Van Wezel Performing Arts Hall to name a few. Only 3 miles or less to Lido Beach, St. Armand’s Circle and Longboat Key. Only 4 miles to Sarasota Bradenton International Airport. Easy to show. $4500 is annual rental rate. Minimum 3-month rental per HOA rules. Sorry NO PETS FOR TENANTS PER HOA RULES.

SARASOTA

226 GOLDEN GATE POINT 44

2 Beds

2 Baths

1,396 Sq.Ft.

$4,500

MLS#: A4665970

Price reduced

Gorgeous views overlooking Sarasota Bay, with your own private beach. Turnkey annual furnished rental includes everything except electric and internet. Just a short stroll to the vibrant downtown arts, culture, award-winning local dining and more. As you enter this spacious over 1,500-square-foot home, you will be drawn to the stunning views of the bay. This rarely available three-bedroom, two-bath end-unit condominium is ready for you, just bring your toothbrush. This lovely home has been given a fresh makeover from stem to stern with stainless steel appliances, granite countertops and wood cabinetry in the kitchen, new baths, all tile throughout, and contemporary furnishings to make this the place to call home. The primary bedroom has a king bed, ample closet space and an updated bath. The second and third bedrooms have queen beds and the guest bath is also updated. One covered parking space along with plenty of guest parking.

SARASOTA

37 SUNSET DRIVE 41

3 Beds

2 Baths

1,675 Sq.Ft.

$4,500

MLS#: A4666714

AVAILABLE IMMEDIATELY. Simply Gorgeous Florida style one story home with beautiful caged swimming pool high and dry above Sarasota Bay. ALSO AVAILABLE FOR SALE $990K NOT AVAILABLE FOR SALE WHEN OCCUPIED. We love this 3 bedroom home turnkey furnished wonderful for an executive or do you have your home for sale? Wonderful WEST OF THE TRAIL home, located in desirable HOLIDAY HARBOR. NO DEED RESTRICTIONS and ONLY 3 MILES to SIESTA KEY! This immaculate 2 BEDROOM PLUS DEN, 2.5 BATH home has much to offer. Upon entering, you are greeted with a view from the foyer that extends across the open-concept living area out to the SPARKLING POOL and the VERY PRIVATE, TROPICAL BACKYARD, ALL NEWLY FENCED. An abundance of natural light, combined with a neutral palette, the home is welcoming in a casual, coastal vibe way. The UPDATED KITCHEN with ample cabinets and a pantry, has a convenient pass through to the SEPARATE DINING ROOM, complete WITH A VIEW TO THE POOL. The spacious owner's suite boasts a huge walk-in closet, an ensuite bathroom, and best of all, FRENCH DOORS TO THE INVITING LANAI. This UNIQUE OUTDOOR LIVING SPACE is ideal for relaxation and entertaining. With the wall mounted TV, you can enjoy the game while BBQing, or lounging in the pool! Beyond the screened in lanai, pavers complete a patio area perfect for your grilling. Back inside, the sun-lit 2nd bedroom adds a coastal cottage feel. The combo half-bath and laundry room extend to more storage space and conveniently, a door out to the pool. A generous sized FLORIDA ROOM overlooking the pool FEATURES NEW IMPACT RESISTANT, ENERGY EFFICIENT WINDOWS AND SLIDERS. The large backyard is landscaped with Florida friendly plantings, including MANGO TREES and Foxtail Palms. A metal roof and hurricane shutters enhance the home's protection. Although this home is safely outside the flood zone, you are only steps away from HIDDEN HARBOR MARINA and the intracoastal waterway to the Gulf of Mexico. It's a boater's dream without the waterfront cost! Keep your boat on your property, or at the marina, or join the Freedom Boat Club and walk to your awaiting boat down the street! Amidst multi-million dollar homes, this family and dog friendly neighborhood, with an OPTIONAL HOA ($10/annual), is definitely a hidden gem in an ideal location. Trellis carport, outdoor storage area, luscious tropical indigenous plants well manicured but yet naturally FLORIDA.

SARASOTA

7860 HOLIDAY DRIVE

3 Beds

2 Baths

2,521 Sq.Ft.

$4,500

MLS#: A4648873

Turnkey Furnished Short-Term Rental Available 1/1/26 - 1/31/26 Only. Recently renovated Mid-Century Modern 3 bedrooms, 2 baths, 1 car garage home just minutes from Downtown Sarasota. Open concept living and dining rooms with cathedral ceilings and wood beams. The Interior and Exterior of the home have been freshly painted. The home has restored Terrazzo flooring throughout. The fully equipped kitchen has new appliances, a pantry, plenty of cabinets for storage, an eat-in countertop that looks out to the living room. The master bedroom has an updated en-suite bathroom with a walk-in shower, the other 2 bedrooms share an updated bathroom with a shower and bathtub. The backyard is fenced and features an amazing paver entertainment area. Walking distance to the YMCA and famous Yoder's Amish Village. Minutes away from world-famous Siesta Key Beach, Lido Beach, St Armand's Circle, museums, and so much more.

SARASOTA

2832 BAY STREET

3 Beds

2 Baths

1,270 Sq.Ft.

$4,500

MLS#: A4668881

Price reduced

Welcome to this beautifully appointed, maintenance free villa in the desirable gated community of the Palisades at Palmer Ranch. Thoughtfully designed and meticulously maintained, this residence offers a spacious great room layout enhanced by soaring ceilings, crown molding, arched architectural details, and a soft, neutral color palette throughout. French doors lead to the screened lanai where peaceful lake views create the perfect backdrop for morning coffee or evening relaxation.

The light-filled kitchen features a charming bay-window breakfast nook, abundant cabinetry, Corian countertops, a natural gas range, double sink, newer appliances, and a generous pantry. The split floor plan ensures comfort and privacy, with the primary suite offering direct lanai access, dual walk-in closets, a relaxing corner tub, separate shower, water closet, and an extended vanity with double sinks. Two additional bedrooms and a full bath provide flexible space for guests, a home office, or hobbies.

Additional conveniences include a full laundry room, a two-car garage, and paver walkways and driveway. This home is located within an intimate community of just 43 residences, known for its Mediterranean inspired architecture, quiet atmosphere, and picturesque lake views. Residents enjoy access to the community pool, pavilion, and outdoor kitchen area ideal for gatherings or quiet afternoons by the water.

Perfectly situated near TPC Prestancia, the Legacy Trail, Gulf Gate Library, Sarasota Sports Club, shopping, dining, and the world renowned Siesta Key Beach, this villa offers a comfortable and convenient lifestyle in one of Sarasota’s most sought after areas.

The lease includes HOA-provided lawn care. Tenants will be responsible for electric, water/sewer, and natural gas services. All utilities will remain in the owner’s name, and the owner will provide the tenant with the monthly utility bills for reimbursement.

SARASOTA

7128 RUE DE PALISADES 22

3 Beds

2 Baths

2,598 Sq.Ft.

$4,500

MLS#: N6141416

Fully furnished beautiful 1 bedroom condo in the heart of downtown Sarasota! That’s right . . . leave your car and walk to your favorite restaurants, shops or the spectacular Bayfront Park & Marina to watch boats go by, visit O’Leary Tiki Bar or Marina Jacks. This is a 2018 built boutique community of only 20 residences - 5 per floor, with a secured entry, controlled elevator access and an assigned parking space on the same level. You’ll feel the fresh and modern design having 42” wood cabinets, granite tops, stainless appliances, modern fixtures and in-unit laundry. Being on the penthouse level, you’ll enjoy 11’ ceilings plus a private terrace with distant water and city views. The impact glass windows and sliders keep city sounds out and gives you peace of mind and storm protection. Available April 1 2024 for 3 months or longer.

SARASOTA

1500 STATE STREET 603

1 Beds

1 Baths

814 Sq.Ft.

$4,500

MLS#: A4499290

AVAILABLE ALL months including 2025 season! This 3 bedroom 2 bath, Bonus Room 1806 square foot home in Gulf Gate is oozing with Southern charm! Will sleep 6. Beautifully remodeled split plan is spacious, open and bright. The updates include a sleek, modern kitchen, upscale bathrooms with gorgeous lighting, beautiful new plank flooring, and beachy coastal colors for the interior and casual Florida furnishings through out the home. The home has everything you need for a perfect stay, including the necessities for days spent at the beach! The backyard is huge, private and you could call it a sanctuary. Perfect backdrop for wonderful gatherings, grilling, or just relaxing and enjoying gorgeous days and balmy nights – Southern style. Gulf Gate Village offers a charming mix of pubs, shopping, exquisite dining, casual dining and entertainment. Only seven minutes away is the world famous Siesta Key, home of the whitest sand in the world. Siesta Key is also home to some of the most gorgeous views on Earth! Miles and miles of beaches, shopping, dining, boutiques, beach bars, music etc. So much to do and see here! Downtown Sarasota is a short 15-minute drive where you will find arts and entertainment, shopping, dining, antiques, boutiques and so much more. Across John Ringling Bridge you’ll find St Armand's Key, which is absolutely worth a visit. Again, the best of the best in dining, shopping, boutiques and gift shops. Current list price is for off season only, please call for seasonal prices.

SARASOTA

6115 CARLTON AVENUE

4 Beds

2 Baths

2,251 Sq.Ft.

$4,500

MLS#: N6123946

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