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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
3,934
# of Listings
2
Avg # of Bedrooms
$491
Avg. $ / Sq.Ft.
$880,172
Med. List Price

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3934 Properties Found. Page 188 of 263.

Gorgeous waterfront condo at The Moorings! You will love the view and the comforts of this well decorated condo in a coastal theme with a stunning view of Blind Pass Intercoastal and a partial view of the Gulf of Mexico just beyond. This community consists of just 17 condos and is on the quieter southern end of Siesta Key. Enjoy your private boat slip or just fish off the dock. Primary bedroom has customized storage and closet area and features a king-sized bed. Beautiful ensuite bathroom is remodeled and updated, as is the guest bath. This space also opens up to the screened in 12 x 10 balcony overlooking the water where there are usually kayakers and paddleboarders. The second bedroom has a queen and a twin bed. You will love the kitchen and eating your meals from bar area where you can view out your large living room window with electric shades. For your convenience, The Siesta Key Trolley, which is a constant running free "hop on" and "hop off" way to get to other areas on the Key, that stops right in from on Midnight Pass Rd. Repeat guest cannot return and this beautiful vacation property just opened up.
#A4620126

SARASOTA

9058 MIDNIGHT PASS ROAD 5

2 Beds

2 Baths

1,371 Sq.Ft.

$7,900

MLS#: A4620126

Escape to Paradise on Siesta Key! Your dream seasonal getaway awaits at 4660 Ocean Blvd Unit N1, Sarasota, FL 34242. Immerse yourself in the tranquil beauty of the Gulf Coast, where pristine sands meet crystal-clear waters. This exquisite 2-bedroom, 2-bathroom condo is your ticket to an unforgettable retreat. Step into your sun-drenched sanctuary, tastefully furnished to embody comfort and luxury. With an unobstructed gulf beach view from your living room and private balcony, every moment is a breathtaking masterpiece. Sip your morning coffee while basking in the warm glow of the sunrise, or unwind with a glass of wine as the sun paints the sky in hues of orange and pink over the horizon. Awaken to the gentle rhythm of the waves and indulge in the ultimate relaxation experience. The spacious living areas are designed for both leisure and entertainment, boasting an open-concept layout that seamlessly connects the fully-equipped kitchen, dining space, and cozy lounge. Whether you're cooking up a gourmet meal or sharing stories with loved ones, every corner exudes a sense of togetherness and joy. Retire to the elegantly appointed bedrooms, each offering a serene haven for rest and rejuvenation. The master suite whispers of opulence, complete with an en-suite bathroom and panoramic ocean vistas. Allow the soothing sounds of the sea to lull you into a peaceful slumber, ensuring you wake up refreshed and ready to seize the day. With a minimum 3-month stay, you have ample time to immerse yourself in the Siesta Key lifestyle. Explore the vibrant local scene, from charming boutiques to world-class dining and entertainment options. Take leisurely strolls along the powdery sands, collecting seashells and creating lasting memories. Don't miss this unparalleled opportunity to live your best life by the beach. Available for occupancy starting January 1, 2027, this condo promises a seamless blend of comfort, luxury, and natural beauty. Secure your slice of paradise today and embark on a journey of sun-kissed days and starlit nights. Contact us now to make this seasonal dream a reality! ? Taxes and fees apply to base rent.
#A4662525

SARASOTA

4660 OCEAN BOULEVARD N1

2 Beds

2 Baths

1,200 Sq.Ft.

$7,900

MLS#: A4662525

Turn-key Furnished with 38ft heated saltwater pool and spa, fully fenced yard, putting area and outdoor kitchen! Welcome to The "Retro Ringling" house, a unique designer home in downtown Sarasota with tons of modern amenities and nostalgic charm- all within a stone’s throw from Main St Sarasota, Payne Park and Legacy Trail & just a few short miles to the white sands of Siesta and Lido Beaches. There’s room for everyone in this 1954 built ranch style home with wide open floor plan and more natural light than any home you’re likely to visit. The Retro Ringling has a front to back living room with seating for 8 people and enormous Jalousie windows that capture the romance of the time. The house comes turn-key furnished! We've appointed the house in mid-century modern designer furniture while preserving the original terrazzo floors and custom tile work in the kitchen and baths. Our home is designed to transport you to a simpler time. Located on a quiet street in the historic Ringling Park neighborhood this home is classic, cozy and convenient. The living room centers around a 65 inch 4K Smart TV with ability to connect to Netflix, Amazon Video and other subscription services using our 200 mbps internet speed. Seating around the TV includes one leather couch, one upholstered queen sleeper sofa, 4 cushioned chairs and 2 bar stools. You will also find a vinyl record player with some classic albums, an oscillating Vornado fan as well as a retro bar stocked with board games and other goodies for all ages. There are 2 bedrooms and 2 full bathrooms as well as a separate cubby space that acts as a 3rd bedroom, (the Siesta Room) with a twin futon. All beds feature premium Lucid Mattresses and hotel grade bedding. The bed configuration is as follows: Bedroom 1: 1 queen bed (Sleeps 2); 2 full beds (sleeps 2 adults or 4 kids) Bedroom 2: 1 King bed (Sleeps 2) Siesta Room (3rd Bedroom): 1 Twin bed (Sleeps 1)- Linens in Orange Cube next to bed. Living Room: 1 Queen Sleeper Sofa (Sleeps 2)- Linens in hallway closet. Both bedrooms have large empty closets with hangers as well as dresser space and nightstands with bedside lamps. The Master bathroom offers a tub/shower combo and the 2nd bath is smaller with a walk-in shower. The eat-in kitchen will make you smile. There’s seating for 6 around a retro tulip table and and the beachy mint tile counters and backsplash set the stage for a brand new Big Chill 1950s style refrigerator with ice maker. There’s also a range/ oven, microwave, toaster over, spice rack, knife block set and coffee maker. The Florida room is spacious with a dining table for up to 8 people and a separate seating area with room for 6 more centered around a 50 inch 4K Smart TV on a swivel mount. This room is not air-conditioned however two ceiling fans provide some relief in the hotter months. This room also has a dart board and a cornhole set to be used out back. Full laundry is available in the garage as well as an iron and ironing board and bench top for folding your clothes. We have a large private, fenced back yard with brand new saltwater pebble tec pool and spa. The pool has also sunshelf with bubbler. There is a mini golf area, a cornhole area and a covered outdoor kitchen. Dogs are allowed with pre-approval and proof of flea/tick treatment. The Retro Ringling offers the best of urban residential living with close proximity to all of the best restaurants and beaches but with room to spread out on a fully fenced private lot.
#A4464508

SARASOTA

2473 DAVIS BOULEVARD

3 Beds

2 Baths

1,376 Sq.Ft.

$7,750

MLS#: A4464508

Beautiful Key West-style three bedroom, two bath, turnkey furnished condo with its own garage in a lush, tropical resort setting. The townhouse, second/third floor condo, is meticulously maintained and beautifully furnished - There's even a teeny "peek-a-boo" water view from the lanai. The furnishings and flooring are stylish and perfect for the beach. The updated kitchen has granite counter tops and stainless steel appliances with a work station looking out to the pool. The beach is a short walk across the street and the restaurants, shopping and clubs of Siesta Key Village are minutes away! **Taxes and fees not included.
#A4594300

SARASOTA

1350 SIESTA BAYSIDE DRIVE 1350-B

3 Beds

2 Baths

1,495 Sq.Ft.

$7,700

MLS#: A4594300

A spacious two bedroom/two bath ground floor home with attached garage. Relax on the private south-facing lanai overlooking a lake featuring a fountain and frequent visits by numerous water birds. After a long day enjoy HDTV and high-speed internet ready to stream your favorite programs. Wireless internet is also available throughout Bayside and at the pools. The living area is tiled, and the bedrooms have newly-installed plank flooring. Updated bathrooms, in-suite laundry and a well-equipped kitchen featuring stainless steel appliances ensure your stay will have all the comforts of home., Just a short walk away is Crescent and Siesta Beach, rated No. 1 beach in the US easily accessed by private deeded access to its renowned white sands and blue waters. The unit is also conveniently located mid-way between the two pools on the Bayside grounds, guests also have access to the newly renovated fitness center and gas BBQ grills and tennis courts. A fishing dock located on the shell lined walking path encircling the property features a fish light attracting a variety of marine life. A ONE WEEK MINIMUM RENTAL IS REQUIRED. IF YOU DESIRE TO STAY MORE THAN ONE WEEK, PLEASE CONTACT US TO HELP YOU BOOK YOUR RESERVATION. **Taxes and fees not included.
#A4591700

SARASOTA

1260 SIESTA BAYSIDE DRIVE 1260-A

2 Beds

2 Baths

1,130 Sq.Ft.

$7,700

MLS#: A4591700

Welcome to our recently updated two-bedroom, two-bathroom second-floor unit in Gulf and Bay - Bayside on Siesta Key. This stunning condo offers a host of modern features and stylish enhancements that will elevate your vacation experience to new heights. With vaulted ceilings creating an open and airy atmosphere, you'll find that every corner of this unit has been thoughtfully designed for your comfort and enjoyment. Step inside, and you'll immediately notice the fresh, inviting ambiance that stems from the recent updates. The entire space has been treated to a fresh coat of paint, breathing new life into every room. It's the perfect backdrop for the beautiful furnishings that adorn the living area, dining area, and lanai. Relax on plush sofas and chairs, enjoying the cozy atmosphere created by the new furniture, which has been carefully chosen for both aesthetics and comfort. The living area seamlessly flows into the kitchen, dining area, and lanai, all of which have been adorned with brand new tile flooring. This not only adds a touch of modern elegance but also ensures a cool and refreshing underfoot experience throughout these spaces. Whether you're preparing a meal in the well-appointed kitchen or dining with loved ones at the stylish table, you'll appreciate the chic, easy-to-clean flooring. When it's time to retreat to your private sanctuary, the bedrooms offer the perfect haven for rest and relaxation. The new carpeting in these spaces provides a soft and plush surface underfoot, making it a joy to step out of bed in the morning. Both bedrooms are tastefully decorated and offer a peaceful ambiance, allowing you to unwind and recharge after a day of Siesta Key adventures. One of the highlights of this unit is the glassed lanai, featuring sliders that allow you to control the flow of fresh air and natural light. Whether you choose to use this space as a cozy reading nook or an additional dining area, you'll appreciate the flexibility it offers. The kitchen has received a stunning makeover with new cabinets and granite countertops. This modern and functional space is equipped with all the appliances and utensils you need to prepare meals and snacks at your leisure. It's a true culinary haven for those who enjoy cooking or simply want to indulge in some homemade treats during their stay. In addition to the remarkable updates within the condo, Gulf and Bay - Bayside on Siesta Key offers a range of amenities to enhance your vacation. Take a dip in the swimming pools, play a game of tennis, or simply relax amidst the beautifully maintained grounds. In conclusion, our recently updated two-bedroom, two-bathroom second-floor unit is a gem within Gulf and Bay - Bayside on Siesta Key. With its vaulted ceilings, fresh paint, new furniture, elegant tile and carpeting, and a modern kitchen, it offers an exceptional and stylish retreat on this beautiful island. Whether you're seeking relaxation or adventure, this condo provides the ideal base for your Siesta Key getaway. Don't miss the opportunity to experience the comfort and luxury of this newly updated vacation rental – book your stay with us today! **Taxes and fees not included.
#A4591706

SARASOTA

1340 SIESTA BAYSIDE DRIVE 1340-C

2 Beds

2 Baths

1,280 Sq.Ft.

$7,600

MLS#: A4591706

Gulf and Bay Club Bayside is one of the most attractive condominium units on Siesta Key. This beautifully remodeled unit offers luxury accommodations at a reasonable cost. Offering a beautiful lake view and steps to the resort-style pool. You will enjoy your stay every minute. Enjoy all of the luxurious amenities this unit has to offer, from comfortable King size bed to the comfy queen-size sofa sleeper suitable for extra guests. This beautiful unit is decorated in true island style that highlights the natural surroundings of Siesta Key. The office features a double futon that is suitable for an extra guest or perhaps two small children. The glass enclosed lanai overlooks the serene lake with lighted fountain. If you choose to cook, it will be a pleasure while using the new appliances and well-equipped kitchen. This fabulous unit offers one and a half bathrooms! Beach gear is provided for your convenience - chairs, umbrella, and beach towels. This immaculate unit is waiting for you! What are you waiting for? Book now and ask for Unit 1313 - life is good! **Taxes and fees not included.
#A4594318

SARASOTA

1313 SIESTA BAYSIDE DRIVE 1313-D

2 Beds

1 Baths

959 Sq.Ft.

$7,600

MLS#: A4594318

Available for 3 months or longer. Located in the much sought-after Laurel Park neighborhood near upscale Main Street. This unique 3BR/2 bath impeccably furnished 1927 Historic home along with a separate 2 car garage. The renovations completed in 2020 were done with care and precision, from floor to ceiling. The new owners have carefully curated the high-end furnishing, artwork and accessories in conjunction with a well-known interior decorator. The property is one of a kind and you will be hard-pressed to find another home of this quality for lease. Featuring wood flooring throughout, the primary bedroom offers a King bed, walk in closet with built-ins, smart TV and is ensuite. The second bedroom is set up as a den with comfortable seating and a Smart TV and plenty of room to work from home. The third bedroom has a Queen bed. The living area has a charming decorative fireplace, and the dining area offers seating for four or more. If you love to cook, you will enjoy the newly renovated Chef's Kitchen with gas cooktop, center island and breakfast bar. The peaceful large backyard has an outdoor deck and a screened Gazebo for dining al fresco. The property is walking distance to the Marina and Shelby Gardens as well as the great restaurants and shops on Main Street. The property is minutes from Armand Circle and easy short bike ride or drive to Lido and Siesta beach. Sarasota’s finest in a quiet residential area with great school districts. Ideal for the reassigned executive or for those looking for luxury during relocation or renovation. (Booked January through end of March 2026)
#A4588664

SARASOTA

1716 OAK STREET

3 Beds

2 Baths

1,689 Sq.Ft.

$7,500

MLS#: A4588664

DOWNTOWN SARASOTA TOWNHOUSE AVAILABLE AT THE Q AVAILABLE FOR THE 2026 SEASON! The three level townhouse with elevator and garage, features fine finishes and furnishings for your winter escape. The home has a light-filled interior with high ceilings and multiple outdoor areas, including a large rooftop terrace and garden, the perfect place for relaxing or entertaining. The downtown Sarasota location is steps away from dining, shopping, and entertainment. A short drive over the Ringling Causeway takes you to Lido Key Beach and St. Armand’s Circle. 3 month minimum. LEASED 11/1/25 TO 5/2/26
#A4643564

SARASOTA

241 COSMOPOLITAN COURT

2 Beds

2 Baths

2,844 Sq.Ft.

$7,500

MLS#: A4643564

Available May 2026. Direct beach front condo on Siesta Key beach. This unit has it all for that Florida vacation. 2 bedroom, 2 baths, located on the 2nd floor with private lanai. Living room and dining area face the Gulf of Mexico which allows for beautiful sunsets. The condo is tastefully decorated with wood and tile floors. Cool off in the pool located next to the unit, take a walk along the pristine sugary quartz sandy beach or take a swim in the turquoise waters of the Gulf. Just a short distance to shopping, dining and nightlife of Siesta Key Village.
#A4481650

SARASOTA

460 BEACH ROAD A1

2 Beds

2 Baths

1,363 Sq.Ft.

$7,500

MLS#: A4481650

Lovely pool home located in PALMER RANCH...perfect SEASONAL getaway! Three bedrooms + a den/office, 3 baths, 2 car garage. Beautifully decorated with all the comforts of home. Split floor plan features formal living and dining rooms, a spacious master suite with his and her closets, a King size bed and large en-suite bathroom. The two guest bedrooms are tastefully furnished with a queen bed and two XL twin beds. The main rooms and master open to the beautiful heated pool and spacious travertine deck perfect for entertaining or just relaxing. The eat in kitchen is open to the family room and features stainless appliances, granite countertops, custom cabinets and a great pool view. Laundry room with large washer/dryer and a utility sink. Wifi, HD cable and premium channels included. Small dogs allowed with owners approval. SARASOTA FLORIDA, VACATION RENTALS, LUXURY PROPERTIES.
#A4492242

SARASOTA

7348 STANHOPE COURT

3 Beds

2 Baths

2,828 Sq.Ft.

$7,500

MLS#: A4492242

Discover your own slice of paradise at Jamaica Royale! This beautifully updated and tastefully decorated 1-bedroom, 1-bathroom condo is just steps from the refreshing waters of heated Pool #1 and a short stroll to the world-famous, powdery whit e sands of Siesta Key Beach. Enjoy the convenience of your assigned covered parking space located right outside your door. Inside, the condo is thoughtfully furnished and generously equipped for your home-away-from-home experience. The kitchen comes fully stocked with modern appliances, including a dishwasher, while the spacious bedroom features a comfortable king bed and ample closet and drawer space. A sleeper sofa in the living room offers additional accommodations, and a washer/dryer inside the unit adds extra ease. Step outside to soak in breathtaking sunsets or wander along Jamaica Royale’s private 300-foot stretch of beach, complete with lounge chairs exclusively for guests. Two Tiki huts provide shady retreats, while three heated pools ensure plenty of space to relax. The community also offers two BBQ grills—one beachside and another on the patio at the front—perfect for casual dining. Private cabanas are also available through the onsite office. For added fun, the public beach is just 1/4 mile away, where you’ll find tennis and volleyball courts, yoga classes, special events, and a new concession stand serving gourmet beach fare. On Siesta Key itself, enjoy a variety of restaurants, shopping, and grocery stores, all easily accessible with free local ride services. Beyond the Key, explore Sarasota’s wealth of attractions, from world-class museums and golf courses to vibrant shopping districts and scenic parks. Whether you’re seeking relaxation, adventure, or a bit of both, this Jamaica Royale condo is your perfect retreat in paradise.
#A4665342

SARASOTA

5830 MIDNIGHT PASS ROAD 54

1 Beds

1 Baths

988 Sq.Ft.

$7,500

MLS#: A4665342

Frist time available to rent. Enjoy urban luxury living in Personal Residence1001, Rivo @ Ringling, 1771 Ringling Blvd, Sarasota FL 34236. Nestled in the vibrant heart of downtown Sarasota, FL. This exquisite two-bedroom, two-bathroom unit at Rivo at Ringling offers a bonus room to office in with Murphy Bed for your short term visitors. Westward views and the downtown lifestyle. The ideal destination for vacationers, professionals on the move, and anyone seeking a blend of comfort and convenience. Why would you ever leave home? As you step into this stunning 10th-floor retreat, you're greeted by a dramatic view that draws you into the residence. The impact windows and hurricane glass floor-to-ceiling sliders usher in natural light and open to a charming covered balcony. Here, panoramic views of the city westward skyline set the stage for intimate dinners or people watching during Main Street events. The kitchen, a delight for culinary enthusiasts, boasts granite countertops, stainless steel appliances, and an inviting openness to the cafe dining area. A Bonus Room, equipped with a Murphy Bed and built in closet, offers additional sleeping quarters or a tranquil space for leisure activities or office. Retire to the master bedroom suite where indulgence awaits with California King-size accommodations, premium bedding, a substantial walk-in closet, and an en-suite bathroom crafted for relaxation. The second bedroom, featuring a Queen platform bed, is a serene sanctuary for your guests. Added conveniences include a separate utility room with a full-size stackable washer and dryer, and two secure parking spaces inside the building garage. The Rivo at Ringling is more than just a residence; it's a lifestyle. Residents enjoy concierge type service, a fitness center, heated pool and spa, community grill, party room, and bike storage. Its unparalleled location places you within steps of Sarasota's finest theaters, diverse dining options, boutique shopping, the Bayfront, St. Armand's Circle, and the pristine beaches of Lido and Longboat Key. The Association does not allow Pets for tenants or visitors.
#A4646786

SARASOTA

1771 RINGLING BOULEVARD 1001

3 Beds

2 Baths

1,984 Sq.Ft.

$7,500

MLS#: A4646786

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

An Ascendia Property! **Listing reflects monthly rate. Unit can be rented on a 1-Week minimum basis - call us today for weekly pricing!** Welcome to your BOHO CHIC beach retreat located near the famous Crescent Beach on Siesta Key! You'll feel right at home when you stay in this 2 bedroom, 2 bathroom (sleeps 5) condo. Spend time cooking your favorite meals in the fully stocked kitchen... Cozy up on the couches in the living room to watch your favorite movies... Take a seat in your screened lanai to read a good book... but remember.. you're in SIESTA KEY! Enjoy relaxing days by the community pool or walk across the street and spend time playing or just laying in the sand! You will also have access to the laundry room that is on-site, just a few steps outside the front door! Looking for a GREAT LOCATION?? You've found it! You will be located in the quiet community called Vista Hermosa, which has amazing walkability! Walk to Point of Rocks beach access (no. 12 & 13), where you can snorkel, fish, swim, and search for the perfect shells! You can also walk to Siesta Key's South Village, where you will find shops, restaurants, and entertainment including long standing local favorite Captain Curt's! Book today, everything you need for a perfect beach vacation is here! **ESSENTIALS: This property is a vacation rental and comes fully equipped with everything you will need such as pots, pans, linens, towels including pool/beach towels, beach wagon, beach chairs, and all the beach gear you will need! **LAUNDRY: Coin laundry is available for your convenience! **To book this unit a REFUNDABLE security deposit is required.**
#A4607431

SARASOTA

116 VISTA HERMOSA CIRCLE 308C

2 Beds

2 Baths

980 Sq.Ft.

$7,500

MLS#: A4607431

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