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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

4,577

# of Listings

2

Avg # of Bedrooms

$485

Avg. $ / Sq.Ft.

$872,674

Med. List Price

Browse Downtown Sarasota Real Estate Listings

Under $250,000

$250,000 - $500,000

1787 Properties Found. Page 41 of 120.

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

SARASOTA

2921 CAPTIVA DRIVE

4 Beds

2 Baths

1,905 Sq.Ft.

$7,500

MLS#: A4641886

Annual 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 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.

$7,500

MLS#: A4657611

This lovely Bird Key garden home resides on a corner lot with a large circular paver driveway and beautiful landscaping that leads to the front door with the 2 car garage located on the side of the house. Inside, you will find abundant natural light with many windows and glass sliders that afford a splendid view of the large yard and pool area with a private garden wall. This three-bedroom residence has a split floor plan offering a private master suite, complete with 2 walk-in closets, an en-suite bathroom, and sliding doors to the pool deck. The two guest bedrooms and a second bathroom complete the other end of the house. A powder room and an oversized laundry room with a sink and loads of storage are a bonus not found in many garden homes. The kitchen overlooks the large backyard and pool area, with granite countertops, stainless steel appliances, and a breakfast bar overlooking the family/dining room. The house has high-impact windows & sliding doors, a heated pool, a well for irrigation, and mature lush landscaping that provide privacy and a large fenced back yard. The most recent upgrades and improvements from the interior to the exterior include re-ling the plumbing under the slab. The garage was gutted, painted and the floor epoxied. Updated interior baseboards and stunning interior lighting were installed throughout the home, giving it an updated, sleek look. This home is move-in ready. Live the comfortable Florida dream by opening large sliders to the pool area, with neutral tile throughout and a spacious flowing floorplan that makes the indoor-outdoor lifestyle easy. This residential island has its own optional Bird Key Yacht Club, tennis courts, swimming pool, fitness room, social scene, boat slips, marina, indoor and outdoor dining. These are the perfect ingredients for making this your private island retreat, complete with nearby beaches, dining, shopping, excellent schools, and the beautiful downtown area.

SARASOTA

605 WILD TURKEY LANE

3 Beds

2 Baths

3,189 Sq.Ft.

$7,500

MLS#: A4650327

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!

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.

SARASOTA

1338 SIESTA BAYSIDE DRIVE 1338-C

2 Beds

2 Baths

1,280 Sq.Ft.

$7,400

MLS#: A4592999

You will Never Want to Leave this 4-bedroom house on Siesta Key! Mid-Century Modern, 4 bedroom home with saltwater, heated Pool with canal views. Located within a 6 minute bike ride to Siesta Key's Beach Access #5 and walking distance to everything that Siesta Key Village has to offer. This unique 1950's built, partially renovated, 4 bedroom, 3 full bath, "Sarasota School of Architecture style" pool home brings a blend of both vintage and urban accents, make this home TRULY unique and one of a kind! From the stainless steel front door & glass foyer, to walls of glass for incredible views. Fully furnished price is $8400, unfurnished $7400. Lawn and pool care included.

Cook gourmet meals in this spacious, beautifully updated kitchen with a skylight allowing natural light to shine in, built in double ovens, glass cook top range, solid slate countertops. The kitchen dining area includes incredible water views!

Open the multiple sets of sliding glass doors to the covered lanai and pool deck. The luscious, mature landscaping surrounding this property, add to the feel of a tropical, one of a kind, getaway.

The spacious master bedroom suite with king sized bed features multiple sliding glass doors leading out to the pool and deck with walls of glass for incredible views of water, a large sitting area plus original built-ins and an en-suite modern, upscale bath with walk-in tiled shower. The second bedroom has a queen bed, closet, and includes a door leading out to front patio area.

The third and fourth bedrooms have queen beds, with closets and lots of natural light. One opens up to the front and one has its own on-suite bath and separate seating area leading to the back pool and canal. This area can be completely closed off for as a private suite.

There is a big, circular drive for parking and a shed for additional storage space with sufficient space to store your bicycles for riding into town and to the beach. Stacked washer and dryer off the kitchen for your convenience.

6500 LB boat lift for boat up to 23', only 1 bridge to bay (Grand Canal bridge).

SARASOTA

5153 SANDY COVE AVENUE

4 Beds

3 Baths

4,117 Sq.Ft.

$7,400

MLS#: A4625973

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!

SARASOTA

116 VISTA HERMOSA CIRCLE 210C

2 Beds

2 Baths

980 Sq.Ft.

$7,200

MLS#: A4578083

Indulge in the ultimate relaxation experience at our exquisite vacation rental in Gulf and Bay - Bayside on Siesta Key. This meticulously appointed condo offers an abundance of space and comfort, allowing you to unwind in style. From savoring a glass of fine wine on the expansive lanai to reveling in the convenience of a fully equipped, turnkey furnished unit complete with a washer/dryer and a private garage, this getaway promises an unforgettable retreat.

As you step into this luxurious condo, you'll immediately be greeted by an atmosphere of tranquility and sophistication. The spacious living area beckons you to sink into plush seating, where you can kick back and watch your favorite shows on a state-of-the-art entertainment system or simply relish in the serene ambiance. Whether you're traveling with family or friends, the open layout of this condo ensures that there's ample room for everyone to relax and enjoy.

Prepare delectable meals in the fully equipped kitchen, boasting modern appliances, granite countertops, and all the culinary essentials you need. The adjacent dining area invites you to savor your creations in style, with seating for all your guests. If you prefer dining al fresco, the lanai provides a delightful setting to enjoy your meals while taking in the picturesque views of the surrounding area.

When it's time to rest, you'll find the bedrooms to be havens of comfort and serenity. The master suite boasts a plush king-sized bed, en-suite bathroom, and its own access to the lanai, allowing you to wake up to the gentle breeze and natural beauty of Siesta Key. The additional bedrooms are equally inviting, ensuring that everyone in your group enjoys a peaceful night's sleep.

One of the most remarkable features of this vacation rental is its proximity to Siesta Key's world-renowned white sandy beach on the Gulf of Mexico. Guests are delighted to discover that they are just a short walk away from private beach access, allowing them to bask in the sun, swim in the crystal-clear waters, and witness unforgettable sunsets over the Gulf. Whether you're a beachcomber, a water sports enthusiast, or simply someone who appreciates the beauty of nature, Siesta Key's beach offers an array of activities and sights to relish.

After a day of fun in the sun, return to your condo for a refreshing shower or a soak in the spa-like bathrooms. The convenience of a washer and dryer means you can keep your beachwear fresh and ready for your next adventure.

In addition to the beach, Gulf and Bay - Bayside on Siesta Key offers a range of amenities to enhance your stay, including access to swimming pools, tennis courts, and well-maintained grounds for leisurely strolls. The private garage ensures that your vehicle remains secure and protected during your stay.

In conclusion, our vacation rental in Gulf and Bay - Bayside on Siesta Key is the perfect haven for those seeking an upscale and convenient escape to the paradise of Siesta Key. With its luxurious accommodations, proximity to the beach, and a plethora of amenities, it's the ideal destination for a warm and sunny retreat. Book your stay with us and experience the beauty and serenity of Siesta Key like never before.

**Taxes and fees not included.

SARASOTA

1374 SIESTA BAYSIDE DRIVE 1374-D

2 Beds

2 Baths

959 Sq.Ft.

$7,200

MLS#: A4591689

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.

SARASOTA

1351 SIESTA BAYSIDE DRIVE 1351-D

1 Beds

1 Baths

959 Sq.Ft.

$7,200

MLS#: A4589578

Penthouse Unit! Currently offering 2 months free on a 13+ month lease term and 3 months free on a 22+ months lease term. Prices, promotions, and availability
are subject to change. Multiple floor plans available. Days on market is not specific to this current plan listed. We warmly invite you to bring your client to Aster and Links, where our professional leasing team will showcase the
unparalleled luxury of our community. From our stunning penthouses with rooftop terraces that boast unmatched views of the Sarasota skyline,
to the meticulously designed interiors, every detail is crafted to impress. As you explore, our team will also share the charm of the vibrant
downtown Sarasota neighborhood. Enjoy complimentary refreshments and a seamless, personalized experience that is sure to leave a lasting
impression. We look forward to hosting you!

SARASOTA

1991 MAIN STREET Links B1 PH

3 Beds

3 Baths

2,212 Sq.Ft.

$7,182

MLS#: O6292289

Welcome to Sweet Pineapple! This elegant 2-bedroom, 2-bath private pool home has been fully remodeled in 2022. This home is located just 7.6 miles from the world-renowned Lido Key Beach, where you can enjoy the beach's crystal-clear blue waters and kayak through the mangroves. When you are ready to adventure, head over to Saint Armand's Circle, where you will find exquisite restaurants and lovely boutique shopping. Enjoy the famous Pinecraft Amish Village, where visitors can treat themselves to handmade Amish gifts at Yoder's, Dutch Heritage, and other Pinecraft area restaurants and merchants. Take home locally made jams and jellies, dolls, quilts, soaps, wooden toys, and more. Yoder's has also added a deli and a produce market. Most weekends, a Farmers' Market in Pinecraft sells fruits and vegetables grown by the Amish and their canned and jarred goods. Tamaron Preserve is a slice of nature only four blocks away from this home, where you can walk the shelled trail, feed the turtles and fish, and bring your furry friend for a walk. Upon entry to the home, you will find a lovely front courtyard that will leave you in absolute Zen. There are two chairs out in the front, where you can enjoy your morning cups of coffee and enjoy the sounds of nature. When entering the home, you will find wood vinyl flooring throughout. The living room has a 65" Roku TV, two plush couches, one being a pull-out couch with a queen-size bed, and an adjoining day chair. Adjacent, you will find the kitchen and informal dining room. The dining table can seat up to six comfortably, and there is an leaf extension for larger groups that can then seat up to eight. The kitchen has stunning granite countertops, stainless steel appliances, and a coffee corner. On the other side of the kitchen, you will find the second living room or sunroom which is completed air-conditioned, with a dining table that can seat up to four, and two bar stools on the kitchen island. The table is perfect for games or puzzles and enjoying your morning coffee or lunch overlooking the gorgeous pool. Down the hall, you will find the primary bedroom, a king-size bed, a set of sliding glass doors, a Roku TV for easy streaming, and a large walk-in closet. The primary bathroom has a large vanity and a walk-in shower tiled from floor to ceiling with a detachable showerhead. The second bedroom has two twin XLs that can be put together with a bed extension to convert it into a king-size bed. The second bathroom has a large vanity with chic décor and a shower/tub combo with a detachable showerhead. Time for your outdoor retreat! There is a sizeable free-formed pool that has been completely resurfaced, overlooking the giant backyard. There are four chairs by the pool for you to soak up that Florida sun, along with an outdoor dining table with an umbrella that can seat up to six. The spacious backyard is the perfect place for friends and family to get together. There is an outdoor fire pit and a gorgeous pineapple garden that borders the caged-in pool. House Rule: No smoking. No burning candles inside of lodging. No parties. No Pets. Pool heating is optional, for an additional non-refundable fee of $25 per day + taxes?to be paid directly to the management company after the reservation is confirmed.

**Taxes and fees not included.

SARASOTA

3852 GATEWOOD DRIVE

2 Beds

2 Baths

1,280 Sq.Ft.

$7,150

MLS#: A4533556

One or more photo(s) has been virtually staged. Yes..Yes... Yess Availablewith a Start Date of January 16th 2025. Attractively Priced this Property requires 3 month minimum..
Spend you winter here on Siesta Key. This is an amazing price for an amazing property. Are you dreaming of being surrounded by water??? THIS is the place! The Pointe, located on the southernmost tip of Siesta Key, boats stunning views of Little Sarasota Bay, the lagoon, and the Gulf of Mexico! Enjoy breakfast in your sun-drenched kitchen looking at the Gulf or watch bird and water life from your huge, enclosed, air-conditioned balcony! This association features fitness rooms as well as community rooms in each building, on-site management, a clubhouse with a kitchen, kayaking, fishing, outdoor pavilion, heated pool with spa, lighted tennis courts and fishing- all within a ten-minute walk to Turtle Beach! Turtle Beach features swimming, sunbathing, shelling, playground, parking, restrooms, outdoor shower, boat launch and picnic shower. Also within a ten-minute walk: Turtle Beach Pub as well as Ophelia's on the Bay and Turtles on Little Sarasota Bay! Just minutes from Southbridge on Siesta Key and a short trolley ride to the Village- You'll never want to leave!

SARASOTA

9397 MIDNIGHT PASS ROAD 501

2 Beds

2 Baths

1,630 Sq.Ft.

$7,000

MLS#: A4632835

Please contact the Listing Agent to obtain details about the WEEKLY and MONTHLY rates. Should you wish to rent TWO LUXURY RESIDENCES for a larger gathering of guests (up to 18), consider our alternative property named "Sky Blue Sarasota" (2365 Waldemere St, Sarasota), located next to "SunShine Sarasota" (2375 Waldemere St). Experience unparalleled luxury in this breathtaking new construction Mid Century Modern Residence! Welcome to this newly constructed masterpiece in the highly sought-after Arlington Park neighborhood. This stunning 4-bedroom, 3-bathroom home encompasses over 2,300 sq. ft. of flawless living space, crafted for both practicality and memorable family gatherings. Immerse yourself in the pinnacle of upscale living in this newly built masterpiece, ideally positioned near Siesta Key and the lively core of Downtown Sarasota. This remarkable home presents a perfect fusion of sophistication and comfort, tailored for those who appreciate a luxurious yet cozy lifestyle. Enter your personal haven where a private, heated swimming pool creates a resort-style atmosphere that encourages relaxation and leisure. The beautifully crafted outdoor area offers picturesque settings for enjoying the warm Florida breezes. The interior of the home exemplifies refined living with an open-plan layout that facilitates a seamless transition between the living, dining, and kitchen spaces. The residence is embellished with opulent features, including tiles, fixtures, and contemporary cabinets, adding a hint of European elegance to the environment. Conveniently situated near the shops and dining options of Southside Village and just minutes away from the vibrant downtown area, Marina Jack, St. Armands Circle, and the famous Siesta and Lido beaches, this home provides both luxury and accessibility. The property boasts a stunning FULLY FENCED private backyard with a heated pool, surrounded by lush palm trees.
***Location location location***
Only 6 miles to the SIESTA KEY BEACH and 5 miles to LIDO KEY BEACH. Both beaches have large public parking lots and a concessions stand with good hot food and frozen drinks. Siesta Beach's sand is 99% quartz l which makes it white and powder soft. Siesta Key also has two lively areas for dining. The Siesta Key village has restaurants and a couple stores. Another area by the South bridge has several restaurants.
Grab your FISHING pole and head to the water, just 1.3 miles to the Siesta Dr - north bridge for fishing.
DOWNTOWN is 2 1/2 miles away with restaurants, arts, shopping, Whole Foods and farmers market. Downtown has too many restaurants to name such as: Marina Jack’s, O’Leary Tiki Bar and grill, Owen’s Fish Camp, Mediterraneo. You can also take sightseeing boat cruises.
LIDO KEY is just a couple miles from downtown. It is an exciting spot with lots to do including kayaking/stand up paddle boarding in the mangroves, hang out at Lido Beach or stroll around the restaurants and stores of St Armands Circle.
AIRPORTs: Sarasota-Bradenton International Airport-SRQ (7 miles), Punta Gorda Airport- PDG: (50mi) Clearwater Airport (PIE): (57 mi) Tampa Airport (TPA): (60m)

SARASOTA

2375 WALDEMERE STREET

4 Beds

3 Baths

2,650 Sq.Ft.

$7,000

MLS#: A4654505

Bayside highrise Building with underground parking, elevator, turnkey furnished, secured building, washer and dryer nicely appointed Two heated pools, lighted tennis courts, fishing pier, fitness room and that Beautiful Siesta Beach. Restaurants, Shopping, Theater, Arts, Golfing, Bicycling whatever your pleasure you will find in Sarasota. Peppertree is a Gulf to Bay complex Available January 15 2025 thru whenever.

SARASOTA

1255 PEPPERTREE 201

2 Beds

2 Baths

1,400 Sq.Ft.

$7,000

MLS#: A4444112

LIDO TOWERS!!!
Highly sought after SIXTH Floor 3 bedroom 2.5 bath condo in Lido Towers. Completely remodeled in 2023! Secure Building with Lido Beach Access. Enjoy the Beautiful Sunsets from the Sparkling Sandy Beach Across the Street. Lido Towers features a Heated Pool and Jacuzzi, BBQ on the Patio, Sauna, Clubhouse, Laundry Room on Each Floor, Guest Parking, and a Secure, Gated Building. Kayaking available one block away. Walk to Famous St. Armands Circle to Dine at the wonderful Restaurants or Shop in the Boutiques. Downtown Sarasota just a short drive away.
2024: MAY-JUNE $5500-$7000 plus tax; SEPTEMBER $6000-$8000 plus tax: DECEMBER $6000-$8000 plus tax

SARASOTA

1001 BENJAMIN FRANKLIN DRIVE 604

3 Beds

2 Baths

1,702 Sq.Ft.

$7,000

MLS#: A4515973

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