Vacation Condo Rentals By Owner In Sarasota, FL

Welcome to La Siesta 103! Newly renovated and completely furnished with an upscale beachy vibe. Enjoy your favorite beverage on your private screened in lanai or walk out the ground floor unit and take 200 steps to the white crystal sands of the #1 Beach- Siesta Key! Our unit is located directly across from the beach and comes furnished with beach chairs, beach umbrella, beach and pool towels just bring your bathing suits. Bedroom features a King bed with a cool memory foam mattress by Nectar for a great night’s sleep, walk in closet with three clothes bars, large wall mounted TV and nightstand lamps equipped with USB ports to charge your phone. Unit includes queen convertible couch with upgraded mattress. High speed Wi-Fi and cable are included for those taking a break from the sun and fun. Enjoy watching your favorite shows or sports on the 65” smart TV in the living room. Spacious custom kitchen with new appliances and Keurig coffee maker. La Siesta is conveniently located within walking distance to village of Siesta Key or hop on the free trolly to go to Turtle beach or the Village.

Unit 103- Paradise Awaits

Sarasota, Florida, United States

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$224.19

Bright 1-bedroom condo with peaceful lake views in a quiet residential area of Sarasota.brSiesta Key Beach is a 5–10 minute drive (traffic dependent).brPet-friendly home — all pets welcome with a flat $10 pet fee per reservation, regardless of the number of pets.brGuests enjoy access to a heated community pool and a calm setting close to shopping and dining.brbrLake view – ideal for morning coffee or relaxing eveningsbrbrFully equipped kitchen for everyday cooking and longer staysbrbrBright, open living area suitable for relaxing or remote workbrbrBedroom: King bed with premium linensbrbrLiving area: Queen sleeper sofabrbrComfortably accommodates up to 4 guestsbrbrHigh-speed WiFibrbrEthernet (wired) internet connection available for stable remote workbrbrSmart TVs in every bedroom and the living room, with access to 600+ streaming channels for easy entertainmentbrbrOnsite washer and dryerbrbrBeach essentials provided (chairs, towels, umbrella)brbrFree parking: 1 designated space plus extra guest parkingbrbrContactless self check-in & check-outbrbrWalking distance to Publix, restaurants, and local barsbrbrDowntown Sarasota & St. Armands Circle: approx. 20 minutesbrbrI-75 access: approx. 8 minutesbrbrSarasota-Bradenton Airport (SRQ): 15–20 minutesbrbrTampa International Airport: approx. 60 minutes

Lake View 1BR Condo , Heated Pool Near Siesta

Sarasota, Florida, United States

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Bath

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$171.39

Enjoy views of Sarasota Bay from your balcony , on the 3rd floor in the center of this new waterfront condo . take a dip in the heated pool or spa after a workout in the fitness center. Amenities also include use of kayak, gas BBQ grills by the pool, fire pit, or have your friends pick you up by boat at the day dock. This new condo features the best of everything, all you need to bring is your clothes! There is 1 king bed with ensuite bathroom with shower, and walk in closet, full size washer/ dryer, and 1 den with comfy sofa futon for a guest. Beach chairs, umbrella, cooler provided. Second bathroom has tub shower combo. Kickback, relax, and enjoy everything Sarasota and our condo has to offer- you won't be disappointed! Property is gated and secure entry with security cameras, and underground designated parking . This property is hypoallergenic, so we do not allow any smokers or animals to ensure safety for those with allergies. 1 mile from downtown Sarasota and half a mile to “The Bay Park “

Sarasota Waterfront Condo one mile to downtown with EVERYTHING plus more !

Sarasota, Florida, United States

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Bath

Sleeps

$354.45

Summary:brbr3rd floor unit in the clubhouses located on the beachside of Palm Bay Club, which is steps from the beach. Custom cabinets, granite counters, stainless steel kitchen appliances, screened lanai, 3 LCD TV's, stackable washer/ dryer in unit. WIFI. Complex offers elevators, 2 pools (1 beachside, 1 bayside), tennis and pickleball courts. Beach chairs provided by complex. Sleeps 6 (1 King, 2 Twin, queen air mattress). 1-week minimum.

Palm Bay Club #146

Sarasota, Florida, United States

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Bath

Sleeps

$568.39

Summary:brbrCome stay and relax in this beautiful 2 bedroom, 2 bath condo located in the tower at Palm Bay Club overlooking the world famous white sands of Siesta Key beach. Complex offers two pools (one bayside and one beachside), beach chairs and covered parking for 1 car. Tile flooring with granite countertops and stainless steel appliances. Leather furniture, washer/dryer and smart TVs. WIFI. No pets. No smoking. Sleeps 6 (1 King, 2 Queen). 1-week minimum.

Palm Bay Club #97

Sarasota, Florida, United States

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Bath

Sleeps

$395.47

Experience Sarasota like a local at Canvas RADD. Just minutes from downtown Sarasota, the Rosemary Art & Design District is a vibrant neighborhood known for its creative energy. brbrOnce industrial, it now thrives with galleries, studios, murals, and an expanding mix of restaurants, cafés, and breweries. Walkable and central, it offers easy access to the bayfront and Sarasota’s beaches, all infused with creative energy.brbrWelcome to your perfect Sarasota getaway—this spacious three-story condo with elevator offers the ideal blend of comfort, style, and location. Featuring 3 bedrooms and 3 full bathrooms, there’s plenty of room for families or groups to spread out and relax. brbrThe open-concept living area is designed for gathering, while the loft provides a versatile bonus space complete with a wet bar—perfect for mixing cocktails or entertaining with ease. brbrHead upstairs to your private rooftop retreat, where you can soak up the Florida sunshine, enjoy evening drinks, or take in the beautiful Sarasota skies. Whether you’re here for the beach, dining, or exploring downtown, this home is the perfect home base.

Modern Loft in the Rosemary District-DT Sarasota 2

Sarasota, Florida, United States

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Bath

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$581.95

No parties here!!! Sea Club II -Only those looking for a relaxing, quiet and tranquil get-away with an Old Florida feel. Sea Club II- Private access to Siesta Key is a 5 minute walk. This Unit is on the second floor with stair access only. Discover the beauty of Siesta Key from this superb 2-bedroom condo. With 1 king bed and 1 queen bed, queen sofa bed in living room. Cozy Electric Fire Place, Heated Pool, Area for lounging in the sun, dock area for fishing, Tiki Hut with chairs & charcoal grills. Our Fabulous property offers a comfortable and inviting space for guests- enclosed lanai and a large private deck over looking the Bay with a gas grill and outdoor furniture. You'll find all the essentials you need, including AC, a hair dryer, WiFi, an iron, coin laundry, beach chairs, wagon and umbrella, beach towels. 5 minute walk to Siesta Key Beach. Coin laundry on 1st floor. Pets are not allowed. Minutes from Restaurants, Shopping, Entertainment, Grocery Store and Downtown Siesta Key Village. Public Stop for the Trolly is steps from the Condo Entrance!

Siesta Key Access- Large Deck w/ Bay View: 2-Bdrm Condo-sleeps 6 Heated Pool!

Sarasota, Florida, United States

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Bath

Sleeps

$403.86

The Palm Bay Club on Siesta Key BeachbrEnjoy sunrise to sunset from our great resort that has private bay to beach access . NO roads to cross we are a direct beach front resort.br2 bedroom 2 Bath second fl. unit141brBedroom offers private en-suite , Clean and bright open floor plan, well appointed kitchen ,Central A/C .brResort features 2 heated pools , enjoy the tranquility of the bay from the large hot tub or pool . Fishing pier, tennis & pickle ball courts, gym, laundry , we also offer boat slip

Palm Bay Club Private Balcony Beach Side

Sarasota, Florida, United States

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Bath

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$209.85

This hotel-style water front condo boosts luxury, comfort, and super convenient location! Set along Sarasota Bay, the 2-bedroom residence sleeps 4 (2 adults & 2 kids)-perfect for families and couples. Enjoy easy access to Siesta Beach’s vibrant energy, Longboat Key’s calm beaches, and Lido Beach’s relaxed shoreline. Mnts from downtown Sarasota’s Rosemary District, St. Armands Circle, and Sarasota's arts district. Nearby attractions include performing arts theaters, the historic circus, fishing piers, kids’ parks, and waterfront picnic areas. The gated community offers boating slips with direct bay access, a heated pool, hot tub, kayak launch, gym, elevator, grill, fire pit, EV charging, and more. Driving distance to IMG Academy and Sarasota Memorial Hospital makes this a very accessible option for sports teams, traveling nurses, and digital nomads. Checkout our deeply discounted monthly rates for extended stays.

Sarasota Poolside Stylish Retreat w/Grill, Fishing

Sarasota, Florida, United States

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Bath

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$191.62

Within a short walk to Siesta Key Island, this beautiful newly furnished and decorated condo in a boutique setting is a superb vacation rental for guests seeking an enjoyable and comfortable stay. The seamless flow from the dining, kitchen, living and 2 story enclosed lanai makes this unit perfect for entertaining or relaxing. brThe heated outdoor pool is steps away from the private screened in 2 story furnished lanai with an electric grill. With 2 bedrooms, including a king bed, attached bathroom and outdoor balcony, and a second bedroom offering both queen and full beds, this gorgeous property provides for ample relaxation. The dining area offers a large table with seating for up to 7. The full kitchen provides all of your essentials for many family meals. The living room includes a flat screen tv, cozy sofa bed, recliner and chair for plenty of seating. Have a seat at the kitchen bar or prepare drinks from the unique built in living room bar that includes a wine refrigerator. You'll find all the necessary amenities like a hair dryer, iron, washing machine, dryer, AC and heating. There are beach chairs and 2 brand new cruiser bikes ready for biking to the beach, bars and restaurants. brbrWe love our condominium and think it will help you experience everything Sarasota and Siesta Key has to offer.brbr*Bookings must be made a minimum of 30 days prior to arrival*br* First time renters at Key Point Village are required to submit an application for rent to the HOA which includes a background check. Fees for this application are $100.00 for the first two renters and $40.00 per additional adult. (Information and paperwork will be sent once rental is confirmed) br*Peak months January, February and March require minimum monthly stay**brbrbrbr

Charming 2-bedroom, 2 story unit within a short walk to Siesta Key!

Sarasota, Florida, United States

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Bath

Sleeps

$216.59

This 2 BR/2 BA condo is located on the quiet end of Siesta key with beautiful direct views of the Gulf and Blind Pass located on the Inter-Coastal Waterway. Sit out on your lanai, listen to the sound of the surf and enjoy watching the boats pass by or, if you prefer, join in on the fun! The local marina offers various boat rentals including kayaks, paddleboards, and jet skis. Pull your boat right up to our community dock equipped with cleaning stations. Convenient launch area for paddleboards and kayaks also located on-premise. Walk just a few minutes to beautiful Turtle Beach or enjoy upscale waterfront dining just steps from your condo. brbrFree local shuttle allows you to explore Siesta Key with its many beaches (Siesta Key Beach ranked #1 in the US), restaurants and shopping areas. Take a short drive off the key and visit the world-famous St. Armands Circle located in Sarasota, known for its sophisticated shopping and dining with over 100 boutiques, specialty shops, galleries, and restaurants. Return just in time to watch spectacular sunsets over the ocean from the comfort of your own lanai. brbrThe condo has 2 bedrooms (1 king, 2 twin beds) and 2 full baths, fully equipped kitchen (everything you need to bring out the chef in you), living room with queen sleep sofa, 50” HDTV, Bluray player and printer for your business needs. WiFi and cable included. Additional TV located in the master bedroom. A pocket sliding glass door leads out to fully furnished lanai with ceiling fan. Direct views of the ocean and Inter Coastal Waterway as well as a view of heated swimming pool. Stackable wash/dryer located in the unit with additional washing facilities on-premise.brbrEverything you need to feel at home is provided including toiletries, cleaning supplies, dishes, iron/ironing board, hairdryer, vacuum, linens, pillows, beach towels, beach chairs, beach bag. We provide plastic ware for your convenience should you decide to grill outside and enjoy a meal poolside. brbrPlease note the winter high season, January - March, is a minimum three-month rental. All other dates can be rented on a monthly basis.br

Perfect Location. Beautiful Waterviews. Heated Pool. 2 BD/2 BA

Sarasota, Florida, United States

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Bath

Sleeps

$119.88

The two bedroom, two bathroom condo with luxury memory king-sized and queen-sized beds, all new Whirlpool appliances, granite kitchen countertop, waterproof vinyl floor and two full bathrooms with bathtubs, new furniture with 55 smart TV, wi-fi included, beautiful views from furnished balcony, kitchen, and two bedrooms. Central-aired. Swimming pool, tennis court, and gym are in the premise. Laundry room is in the parking lot, directly cross the condo. Next to Turtle Walkway Park, 1.5 miles to downtown, 4 miles to Bird Key beach, 8.5 miles to Siesta Key beach. Plenty of grocery and convenience stores around the corner. Peaceful and quiet community.

Remodeled 2 bedroom 2 bedroom condo with swimming pool& tennis court in Sarasota

Sarasota, Florida, United States

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Bath

Sleeps

$427.87

Perfect for the whole family, this beautifully appointed, three-bedroom condo is situated within walking distance of the exclusive boutiques, art galleries, and restaurants that downtown Sarasota has to offer. You'll enjoy all of the entertainment, nightlife, and shopping of the city from this convenient, yet secluded, location overlooking the Hudson Bayou.brbrIf you enjoy kayaking, there is no better location! Skip the parking costs and rental fees and take the kayaks that are provided for you down the canal, which is conveniently located in the backyard. Prefer riding a bike Take our bikes for a ride instead. Afterwards, feel free to take the beach chairs and umbrellas also provided to nearby Lido beach in order to soak up the warm Florida sun and calming ocean breezes.brbrAbout the property:brbrThe main entry door is located on the left side of the building with a second entry door located inside of the parking garage. The condo has an elevator, but guests must be able to walk up the steps leading to either entry door in order to enter the building. The first floor includes a bedroom with a full bathroom and access to the patio. The second floor includes the kitchen, a full bathroom, and the living room with balconies overlooking the canal. The third floor includes the master bedroom with its own balcony and full bathroom, the laundry space, as well as another bedroom and full bathroom.brbrParking Garagebrbr2 bikes, 2 kayaks, 4 beach chairs, and 2 beach umbrellas available for guests in garagebrbrShared pool access with neighboring condosbrbrPropane grill located in backyardbrbrWireless Internet Accessbrbr***Guest pets are not permitted.brbr***By booking this property, guest acknowledges that use of the swimming pool, adjacent bayou, and any watercraft including boats or kayaks is entirely at their own risk. The property owner assumes no responsibility or liability for accidents, injuries, or loss of life related to swimming, fishing, boating, kayaking, or any other water-related activities on or near the premises. No lifeguard or supervision is provided, and children must be supervised at all times. Guests are kindly asked to exercise caution and good judgment, and understand they are responsible for their own safety and that of their group while enjoying these amenities.

Brand New Luxury Townhouse in Downtown Sarasota w/Elevator, Kayaks, and bicycles

Sarasota, Florida, United States

3

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Bath

Sleeps

$430.67

Enjoy a peaceful stay at this fabulous 2-bedroom condo in Sarasota. The condo features 2 queen beds, 2 bathrooms with a hair dryer, and essential amenities like an iron and AC. Relax in the soothing ambiance of this cozy retreat in our condo. Screened in Lanai for additional dining space. Close to Siesta Key. Large gazebo for get togethers with outdoor kitchen. We hope you enjoy our condo.

Enchanting 2-bedroom condo with AC in Sarasota

Sarasota, Florida, United States

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Bath

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$186.45

This fully furnished third-floor waterfront condo is centrally located on the West side of “The Strand” and spreads over 896 sq ft, with a generous 120 sq ft patio overlooking the serene Whitaker Bayou. This gated community offers a heated communal pool, a gym, 2x barbeques, a dog run and a kayak launch. Please note that pool temperature may vary depending on outdoor conditions, and during colder weather, it may not always reach the desired setting. The pool is heated seasonally in accordance with Homeowners Association guidelines. Guests are kindly asked to follow all HOA pool rules, including posted hours of operation.brbrWe have taken great care to ensure that you have everything you need to feel at home during your stay.brbr★Living Area:brThe living area has two comfortable couches, a coffee table and a Smart Tv for streaming (for your own login credentials), there is no cable Tv. brOne couch is a convertible sofa with a 54.5 in. x 84.5 in sleeping areabr.br★Kitchen/Dining:brThe kitchen features brand new appliances such as a stove, oven, microwave, fridge, dishwasher, toaster, kettle, drip coffee maker, and a Keurig. It has four bar stools at the kitchen island for dining.brA new sponge, dish soap, trash bags and dishwashing detergent to get you started are included.brbr★Bedroom:brLocated on the right-hand side upon entering the condo, it includes a king sized bed, a closet, dresser and two nightstands with lighting. Bedding & linens are included.brbr★Bathrooms:brThe master bath is connected to the bedroom. It features a bathtub, sink and toilet.brThe half bath is located down the hallway and features a sink and toilet.brTowels, a blow dryer and essential soap products are included.brbr★Patio:brThe patio can be accessed through the large sliding doors and can comfortably host up to 6 people. brIt includes two chairs, a couch, and outdoor dining set.brIt is the perfect location to enjoy the sunsets. brbr★Laundry:brThe washing and dryer machines are located in the master bathroom. brBasic detergents are supplied to start you off.brbr★Parking:brYou have one reserved spot inside the parking garage. brPlenty of uncovered guest parking available on a first-come first-serve basis. brbr★Miscellaneous:brSelf check-in starting 4 pm & self check-out by 10 am.brSecure community with MyEnvera gate system.brCar charging stations available.brIf you wish to receive mail, it must be sent to our Orquera Florida Investment office - Sarasota downtown.brbr★Location:brDowntown Sarasota – 5-10 min drivebrLido Beach - 15 min drivebrSiesta Key Beach - 25 min drivebrWicked Cantina Mexican Restaurant & Subway within walking distance.brNew Bay Park – 5 min drive/10 min walkbrbr★Important Notes & Rules:brAn HOA application is required. The $150 application fee is included in the booking fee. (The fee amount is subject to change)brNo parties and non-smoking.brNo pets, no exceptions. brAC cannot be lower than 70 F and heat cannot be higher than 77 F.brDon't leave doors/windows open when AC/Heat is runningbrFor your safety, swimming is at your own risk, and children must be supervised at all times.brResidence is located on the canal without a fence. Supervise children at all times.brIf you require elevator assistance: Elevators may be temporarily disabled during severe weather. In such instances, stairwells are available in the building.brbr★Add-on:brTraveling with a little one We offer a Pack 'n Play for use during your stay for a one-time fee of $50. This includes clean, fitted sheets for your convenience. Just let us know in advance if you'd like to add this to your booking!brbr★Wildlife Awareness:brFlorida's diverse wildlife awaits responsibly; refrain from direct contact and adhere to safety guidelines. For more information, visit the Florida Fish and Wildlife Conservation Commission. brbrAre you traveling with family or friends We manage other units in The Strand including waterfront condos, just ask us!brbrFind us on FB or IG: Orquera Florida Investments brbrYour unforgettable getaway awaits!

1/1.5 Modern Waterfront Condo with Pool and Fitness Room

Sarasota, Florida, United States

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$149.43

Freshly updated/painted condo with luxurious furnishings and steps to the Gulf of Mexico on exclusive Lido Key. This condo is 100 steps to Lido Beach and only a few blocks to world famous St. Armands Circle where you can go shopping or dine at one of the many restaurants. Enjoy the white sand and turquoise water of the beach and in the evenings unwind with the gulf breeze flowing through one of the two unit's lanais. Whichever your style, this is paradise found. Guests must pass a background check performed by the condo homeowners association. Leases run from the 1st day of a month to the last day of a month.

Luxurious Living Steps to Lido Beach & Walking Distance to St. Armands Circle

Sarasota, Florida, United States

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$254.91

SPECIAL RATE!! 15% DISCOUNTED RENTAL RATE FOR ALL NEW BOOKING THROUGH 12/11/26 brWelcome to Beachside Bungalow at LaSiesta 108. This newly renovated, down to the baseboards, ground floor (no steps Yeah!) 2 bedroom 1 bath features all your comforts of home. The sparkly new fully stocked kitchen with dining area and comfy living room lead to the primary king bedroom and down the hall to 2 twin beds. The bath features a step in shower. Follow the path out the lanai door directly to famous Siesta Beach. This area of the beach features a fantastic playground, pickleball/tennis courts, restrooms, 2 delicious snack / dining areas that serve breakfast, lunch AND dinner selections. The powder white quartz sand leads down to the beautiful water of the gulf watched over by our fantastic lifeguards. Now, go out your front door and you are steps from the heated pool and deck area. There is also a clubhouse area with poolside restrooms, small gym, pool table and ping pong, it also offers a lounge area. For up to 4 guests, you’ll find Beachside Bungalow at LaSiesta perfect for your stay on Siesta Key, Sarasota Florida.

Siesta Key - steps to the beach & pool#108

Sarasota, Florida, United States

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1

Bath

Sleeps

$310.77

Experience Sarasota like a local at Canvas RADD. Just minutes from downtown Sarasota, the Rosemary Art & Design District is a vibrant, up-and-coming neighborhood known for its creative energy. brbrOnce industrial, it now thrives with galleries, studios, murals, and an expanding mix of restaurants, cafés, and breweries. Walkable and central, it offers easy access to the bayfront and Sarasota’s beaches, all infused with creative energy.brbrWelcome to your stylish Sarasota retreat in the heart of the Rosemary Art & Design District! This beautiful 3-bedroom, 2-bathroom condo offers the perfect blend of comfort, convenience, and local charm—ideal for a relaxing getaway, family vacation, or extended stay.brbrStep inside to find a bright, open-concept living space with modern furnishings and plenty of room to unwind. The fully equipped kitchen makes it easy to prepare meals at home, while the spacious living and dining areas are perfect for gathering after a day of exploring.brbrEnjoy your own private courtyard—perfect for morning coffee, evening cocktails, or a quiet moment to relax. Guests also have access to a shared rooftop space, offering a great spot to take in the Florida sunshine, unwind, or enjoy time with friends and family.brbrEach of the three bedrooms is thoughtfully designed for comfort, featuring cozy bedding and ample storage. The primary suite includes a private en-suite bathroom, while the additional bedrooms share a well-appointed second bath—perfect for families or groups.brbrLocated in Sarasota’s vibrant Rosemary Art & Design District, you’ll be just steps away from local art galleries, boutique shops, coffee spots, and some of the area’s best dining. Downtown Sarasota, the bayfront, and popular destinations like St. Armands Circle and Lido Beach are all just a short drive away.

Rosemary District Flat in Downtown Sarasota 3

Sarasota, Florida, United States

3

Bed

Bath

Sleeps

$395.47

Experience Sarasota like a local at Canvas RADD. Just minutes from downtown Sarasota, the Rosemary Art & Design District is a vibrant neighborhood known for its creative energy. brbrOnce industrial, it now thrives with galleries, studios, murals, and an expanding mix of restaurants, cafés, and breweries. Walkable and central, it offers easy access to the bayfront and Sarasota’s beaches, all infused with creative energy.

Modern Loft in the Rosemary District-DT Sarasota 3

Sarasota, Florida, United States

3

Bed

Bath