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Siesta Key, FL Condos for Rent

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  • 4660 Ocean Blvd, Siesta Key, FL 34242
    4660 Ocean Blvd, Siesta Key, FL 34242
    4660 Ocean Blvd, Siesta Key, FL 34242
    /20

    $7,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,305 Sq Ft
    • Meticulous Gulf front condo with unobstructed views of the clear blue water.

    4660 Ocean Blvd, Siesta Key, FL 34242

    FULL GULF & SUNSET VIEWS | TURNKEY FURNISHED | WALK TO SIESTA VILLAGE & BEACHSeasonal rental available for January, February and March of 2027. Taxes are not included in the rent. You will be WOWED by the breathtaking full Gulf and sunset views from this TURNKEY FURNISHED Siesta Key residence! Ideally located within walking distance of the vibrant Siesta Village and the world-famous,

    4660 Ocean Blvd, Siesta Key, FL 34242
  • 1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242
    1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242
    1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242
    /28

    $7,050 Per Month

    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft
    • Condo for Rent

    1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242

    This luxurious condo is in a Gulf-side High-rise and is located on the 7th floor. This condo has 2 bedrooms and 2 full bathrooms.A fully equipped kitchen awaits you with cabinet lighting, a ceiling fan and a breakfast bar for 3. It is supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and a Keurig.The formal dining room

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242
  • 797 Beach Rd Unit 305, Sarasota, FL 34242
    797 Beach Rd Unit 305, Sarasota, FL 34242
    797 Beach Rd Unit 305, Sarasota, FL 34242
    /42

    Call for Price

    • 1 Bed
    • 1 Bath
    • 820 Sq Ft
    • Condo for Rent

    797 Beach Rd Unit 305, Sarasota, FL 34242

    Welcome to Your Slice of Paradise – Crescent Royale 3053D Tour URL: AVAILABILITY, PRICING and BOOKING HERE: Note: 7 day minimum required booking.Fully remodeled and infused with a modern coastal flair, this deluxe one-bedroom, one-bath condo is the ultimate Siesta Key escape. With over 820 square feet of bright, open living space, you’ll find all the bells and

    797 Beach Rd Unit 305, Sarasota, FL 34242
  • 1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242
    1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242
    1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242
    /45

    $9,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242

    Welcome to this beautifully designed 2-bedroom, 2-bathroom first floor condo located in the sought-after Gulf and Bayside Bay Club, offers breathtaking views of the boat harbor and Intracoastal Waterway.The kitchen is a chef's delight, boasting stainless steel appliances and sleek countertops. The living room is the perfect place to kick back and relax after a day of adventure, with

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242
  • 1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242
    1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242
    1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242
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    $7,600 Per Month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242

    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

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1340 Siesta Bayside Dr Unit 1340C, Sarasota, FL 34242
  • 1257 S Portofino Dr Unit 36, Sarasota, FL 34242
    1257 S Portofino Dr Unit 36, Sarasota, FL 34242
    1257 S Portofino Dr Unit 36, Sarasota, FL 34242
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    $4,500 Per Month

    • 1 Bed
    • 2 Baths
    • 780 Sq Ft
    • Condo for Rent

    1257 S Portofino Dr Unit 36, Sarasota, FL 34242

    Siesta Key vacation rental! Siesta Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing 1 bedroom has 2 full baths, and is conveniently located on the ground floor close to your assigned parking space. Owner has an air mattress available for guests, a portable electric grill, bikes, beach chairs, and a new 10X10 beach canopy. An open

    Margaret Young JENNETTE PROPERTIES, INC.

    1257 S Portofino Dr Unit 36, Sarasota, FL 34242
  • 1200 E Peppertree Ln Unit 303, Sarasota, FL 34242
    1200 E Peppertree Ln Unit 303, Sarasota, FL 34242
    1200 E Peppertree Ln Unit 303, Sarasota, FL 34242
    /31

    $7,000 Per Month

    • 2 Beds
    • 11 Baths
    • 1,200 Sq Ft
    • Condo for Rent

    1200 E Peppertree Ln Unit 303, Sarasota, FL 34242

    This property is a 30 night minimum.1200-303 is a Bay side Mid-rise unit, located approximately 150 yards away from the Bay.Newly remodeled kitchen with stainless steel appliances. Grab bars located in both bathrooms. Guest bedroom T.V is mounted on the wall. Assigned covered parking located in parking garage.Approx. 1250 Sq. Ft. (1375 including the lanai) Condo Summary:Bedding:

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1200 E Peppertree Ln Unit 303, Sarasota, FL 34242
  • 1215 S Portofino Dr Unit 308, Sarasota, FL 34242
    1215 S Portofino Dr Unit 308, Sarasota, FL 34242
    1215 S Portofino Dr Unit 308, Sarasota, FL 34242
    /30

    $4,000 Per Month

    • 2 Beds
    • 2 Baths
    • 991 Sq Ft
    • Condo for Rent

    1215 S Portofino Dr Unit 308, Sarasota, FL 34242

    BEAUTIFUL WATERFRONT CONDO IN SIESTA HARBOR! CANAL VIEWS • BEACH ACCESS • BOAT SLIPS ON SITE REASONABLY PRICE, CHECK AVAILABILITY. Condo available through January 15, 2027 or April 2027! Step into coastal luxury in this private, beautifully furnished corner end-unit in the highly sought-after Dolphin Building of Siesta Harbor. Enjoy gorgeous water views of the canal from your enclosed hurricane

    Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

    1215 S Portofino Dr Unit 308, Sarasota, FL 34242
  • 1315 Siesta Bayside Dr Unit 1315B, Sarasota, FL 34242
    1315 Siesta Bayside Dr Unit 1315B, Sarasota, FL 34242
    1315 Siesta Bayside Dr Unit 1315B, Sarasota, FL 34242
    /50

    $8,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,645 Sq Ft
    • Condo for Rent

    1315 Siesta Bayside Dr Unit 1315B, Sarasota, FL 34242

    Welcome to this stunning 2-bedroom, 2-bathroom lakefront condo located on the second floor in Gulf and Bay Bayside, Siesta Key. This two-story retreat features two primary bedrooms, each with a luxurious king-size bed, spacious walk-in closets, and beautifully appointed bathrooms with walk-in showers. In the second floor primary bedroom there is additional sleeping accommodations with a full-size

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1315 Siesta Bayside Dr Unit 1315B, Sarasota, FL 34242
  • 1272 Siesta Bayside Dr Unit 1272C, Sarasota, FL 34242
    1272 Siesta Bayside Dr Unit 1272C, Sarasota, FL 34242
    1272 Siesta Bayside Dr Unit 1272C, Sarasota, FL 34242
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    $9,300 Per Month

    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    1272 Siesta Bayside Dr Unit 1272C, Sarasota, FL 34242

    Spacious two bedroom/two full bathroom vacation rental at the Gulf and Bay Club Bayside. Private beach access – 5 minute walk. Tile floors throughout and completely re-decorated and furnished with many amenities for your family’s enjoyment. King bed in the master and two doubles in the guest room.*Taxes and fees not included.

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1272 Siesta Bayside Dr Unit 1272C, Sarasota, FL 34242
  • 1215 S Portofino Dr Unit 202, Sarasota, FL 34242
    1215 S Portofino Dr Unit 202, Sarasota, FL 34242
    1215 S Portofino Dr Unit 202, Sarasota, FL 34242
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    $6,500 Per Month

    • 2 Beds
    • 2 Baths
    • 929 Sq Ft
    • Condo for Rent

    1215 S Portofino Dr Unit 202, Sarasota, FL 34242

    BEAUTIFUL WATERFRONT CONDO ON SIESTA KEY AVAILABLE NOW AND the month of January! CANAL VIEW • BEACH ACCESS • BOAT SLIPS UPON AVAILABILITY - REASONABLY PRICED. Now available In Season and as an annual Rental! Private, beautifully furnished condo with a gorgeous view of the Harbor and Sailboat Water Canal in Siesta Harbor. Enjoy water views of the canal from your enclosed balcony and just a quick,

    Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

    1215 S Portofino Dr Unit 202, Sarasota, FL 34242
  • 1230 Siesta Bayside Dr Unit 1230D, Sarasota, FL 34242
    1230 Siesta Bayside Dr Unit 1230D, Sarasota, FL 34242
    1230 Siesta Bayside Dr Unit 1230D, Sarasota, FL 34242
    /23

    $6,900 Per Month

    • 2 Beds
    • 2 Baths
    • 959 Sq Ft
    • Condo for Rent

    1230 Siesta Bayside Dr Unit 1230D, Sarasota, FL 34242

    This fabulous, updated, one-bedroom PLUS separate sleeping den easily sleeps four guests. The den has a queen size bed for additional sleeping space - Complete with a closet and door for privacy.Relax in the spacious living area or enjoy a glass of wine on the lanai where you can enjoy watching the multitude of birds who visit each day.The condo is turnkey furnished including a

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1230 Siesta Bayside Dr Unit 1230D, Sarasota, FL 34242
  • 5780 Midnight Pass Rd Unit 609, Sarasota, FL 34242
    5780 Midnight Pass Rd Unit 609, Sarasota, FL 34242
    5780 Midnight Pass Rd Unit 609, Sarasota, FL 34242
    /73

    $10,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,361 Sq Ft
    • Condo for Rent

    5780 Midnight Pass Rd Unit 609, Sarasota, FL 34242

    Welcome to Gulf Horizon, your luxurious coastal escape at the Gulf & Bay Club in beautiful Siesta Key. Professionally managed by Gulf Coast Vacations, this stunning 2-bedroom, 2-bathroom sixth-floor gulf-view condo offers the ultimate blend of elegance, comfort, and breathtaking scenery in one of the island’s most exclusive beachfront communities.From the moment you step into the elegant

    Andy Moore GULF COAST REALTY & MANAGEMENT

    5780 Midnight Pass Rd Unit 609, Sarasota, FL 34242
  • 1700 Cove II Place Unit 310, Sarasota, FL 34242
    1700 Cove II Place Unit 310, Sarasota, FL 34242
    1700 Cove II Place Unit 310, Sarasota, FL 34242
    /78

    $2,950 Per Month

    • 2 Beds
    • 1.5 Baths
    • 860 Sq Ft
    • Condo for Rent

    1700 Cove II Place Unit 310, Sarasota, FL 34242

    Available 2950.00 Monthly - April 20th 2026 through December 31st 2026... Not Available 2027 Jan through April 15th 2027 Stunning Water Views & Deeded Beach Access | Siesta Key plus taxes and fees. Live your Dream on Siesta Key for the Summer...Welcome to your perfect beach getaway! This 2-bedroom, 1.5-bath condo in Midnight Cove II offers breathtaking water views from both the unit and the

    Robert Bevington SHOWTIME REALTY

    1700 Cove II Place Unit 310, Sarasota, FL 34242
  • 1275 Siesta Bayside Dr Unit 1275B, Sarasota, FL 34242
    1275 Siesta Bayside Dr Unit 1275B, Sarasota, FL 34242
    1275 Siesta Bayside Dr Unit 1275B, Sarasota, FL 34242
    /38

    $8,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,645 Sq Ft
    • Condo for Rent

    1275 Siesta Bayside Dr Unit 1275B, Sarasota, FL 34242

    Welcome to this stunning second-level condo nestled within the prestigious Gulf and Bay Club Bayside in the serene enclave of Siesta Key. Boasting breathtaking views of the shimmering lake, this meticulously designed residence offers the epitome of luxurious coastal living.As you step inside, you are greeted by an inviting ambiance that seamlessly blends modern elegance with coastal

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1275 Siesta Bayside Dr Unit 1275B, Sarasota, FL 34242
  • 1250 N Portofino Dr Unit 302, Sarasota, FL 34242
    1250 N Portofino Dr Unit 302, Sarasota, FL 34242
    1250 N Portofino Dr Unit 302, Sarasota, FL 34242
    /20

    $3,150 Per Month

    • 2 Beds
    • 2 Baths
    • 929 Sq Ft
    • Condo for Rent

    1250 N Portofino Dr Unit 302, Sarasota, FL 34242

    55+ Harbor View Haven on Siesta Key w/beach access! Discover relaxation and adventure at our Siesta Harbor condo on Siesta Key. This bright 2 bedroom unit offers modern comfort and stunning harbor views from the screened porch. Enjoy deeded beach access and watch breathtaking sunsets. You'll have access to amenities like a fishing pier, boat slips, a pool, and clubhouse activities. Whether you're

    Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

    1250 N Portofino Dr Unit 302, Sarasota, FL 34242
  • 4660 Ocean Blvd Unit G1, Sarasota, FL 34242
    4660 Ocean Blvd Unit G1, Sarasota, FL 34242
    4660 Ocean Blvd Unit G1, Sarasota, FL 34242
    /38

    $2,800 Per Month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Condo for Rent

    4660 Ocean Blvd Unit G1, Sarasota, FL 34242

    Discover your sunlit retreat in the desirable waterfront community of Sea Village on Siesta Key! This ground-floor, 2-bedroom, 2-bathroom condo offers a bright and spacious living environment. The open kitchen is perfect for those who enjoy cooking, and the living area provides ample space for relaxation and entertaining. Each bedroom is a comfortable haven with custom closets for added

    Beth Dilley ASCENDIA REAL ESTATE

    4660 Ocean Blvd Unit G1, Sarasota, FL 34242
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /38

    $9,350 Per Month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    Unlisted Address

    Make yourself at home in our spacious two bedroom, two bath second floor condo located at the beautiful Gulf and Bay Club Bayside. The Key West style cluster buildings afford you a quiet residential feel while you are just a short walk to the powdery white quartz sand of the world famous Siesta Key/Crescent Beach.New to the rental program, our condo has previously been owner occupied and

    Andy Moore GULF COAST REALTY & MANAGEMENT

    Unlisted Address
  • 420 Beach Rd Unit 706, Sarasota, FL 34242
    420 Beach Rd Unit 706, Sarasota, FL 34242
    420 Beach Rd Unit 706, Sarasota, FL 34242
    /34

    $6,000 Per Month

    • 3 Beds
    • 2 Baths
    • 2,022 Sq Ft
    • Condo for Rent

    420 Beach Rd Unit 706, Sarasota, FL 34242

    Experience elevated beachfront living in this rarely available, higher-floor, 2,415-square-foot Gulf-front retreat. Offered as a long-term rental. This expansive three-bedroom, two-bathroom unit seamlessly blends refined comfort with panoramic Gulf views, catering to the most discerning rental client. Triple sliding glass windows flood the open-concept living area with natural light, capturing

    Katie Cintron COLDWELL BANKER REALTY

    420 Beach Rd Unit 706, Sarasota, FL 34242
  • 460 Beach Rd Unit A1, Sarasota, FL 34242
    460 Beach Rd Unit A1, Sarasota, FL 34242
    460 Beach Rd Unit A1, Sarasota, FL 34242
    /15

    $8,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,363 Sq Ft
    • Condo for Rent

    460 Beach Rd Unit A1, Sarasota, FL 34242

    Leased 2027 season! Available 7/1/2026-12/31/2026. 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

    Brenda Cozy COLDWELL BANKER REALTY

    460 Beach Rd Unit A1, Sarasota, FL 34242
  • 1344 Siesta Bayside Dr Unit 1344D, Sarasota, FL 34242
    1344 Siesta Bayside Dr Unit 1344D, Sarasota, FL 34242
    1344 Siesta Bayside Dr Unit 1344D, Sarasota, FL 34242
    /24

    $9,300 Per Month

    • 2 Beds
    • 2 Baths
    • 959 Sq Ft
    • Condo for Rent

    1344 Siesta Bayside Dr Unit 1344D, Sarasota, FL 34242

    This fabulous two bedroom features the primary bedroom with a King bed and the guest with a queen bed. The spacious living area opens onto a tiled lanai surrounded with sliding windows/doors that can be opened or closed as desired. Enjoy your breakfast there in the morning sun or relax with a glass of wine as the sun sets.The condo is turnkey furnished including washer / dryer and private

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1344 Siesta Bayside Dr Unit 1344D, Sarasota, FL 34242
  • 1374 Siesta Bayside Dr Unit 1374D, Sarasota, FL 34242
    1374 Siesta Bayside Dr Unit 1374D, Sarasota, FL 34242
    1374 Siesta Bayside Dr Unit 1374D, Sarasota, FL 34242
    /24

    $7,200 Per Month

    • 2 Beds
    • 2 Baths
    • 959 Sq Ft
    • Condo for Rent

    1374 Siesta Bayside Dr Unit 1374D, Sarasota, FL 34242

    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

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1374 Siesta Bayside Dr Unit 1374D, Sarasota, FL 34242
  • 1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242
    1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242
    1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242
    /51

    $8,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,495 Sq Ft
    • Condo for Rent

    1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242

    Experience coastal living at its finest in this 3-bedroom, 2-bathroom second-floor lakefront condo located in the desirable Gulf and Bay Club Bayside community in Siesta Key. With breathtaking views of the lake, pool, and tennis court from the screened-in lanai, this home is a perfect retreat. The kitchen is equipped with stainless-steel appliances, and the adjacent dining table offers a great

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242
  • 5740 Midnight Pass Rd Unit 303, Sarasota, FL 34242
    5740 Midnight Pass Rd Unit 303, Sarasota, FL 34242
    5740 Midnight Pass Rd Unit 303, Sarasota, FL 34242
    /51

    $6,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,337 Sq Ft
    • Condo for Rent

    5740 Midnight Pass Rd Unit 303, Sarasota, FL 34242

    This luxury Siesta Key beachfront unit in the exclusive Gulf and Bay Club offers full panoramic views of the Gulf of Mexico and the #1 beach in the USA, Siesta Key! This beautifully updated 2-bedroom, 2-bathroom unit features hardwood floors, granite countertops, and an abundance of cabinet space. The bathrooms are elegantly updated with tile and granite counters, making this a truly turnkey

    Robert Bevington SHOWTIME REALTY

    5740 Midnight Pass Rd Unit 303, Sarasota, FL 34242
  • 1200 E Peppertree Ln Unit 402, Sarasota, FL 34242
    1200 E Peppertree Ln Unit 402, Sarasota, FL 34242
    1200 E Peppertree Ln Unit 402, Sarasota, FL 34242
    /32

    $8,300 Per Month

    • 2 Beds
    • 2 Baths
    • 1,163 Sq Ft
    • Condo for Rent

    1200 E Peppertree Ln Unit 402, Sarasota, FL 34242

    This condo is a 30-night minimum.Condo 1200-402 at Peppertree Bay on Siesta KeyThis 2 bedroom, 2 bathrooms recently remodeled, is only steps away from Crescent Beach and is located on the 4th floor.This condo comfortably sleeps 6 guests.The master King bedroom is equipped with a 43'' Smart TV for your entertainment and a ceiling fan. The master bathroom has a walk-in

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1200 E Peppertree Ln Unit 402, Sarasota, FL 34242
  • 4660 Ocean Blvd Unit Q, Sarasota, FL 34242
    4660 Ocean Blvd Unit Q, Sarasota, FL 34242
    4660 Ocean Blvd Unit Q, Sarasota, FL 34242
    /26

    $7,999 Per Month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Condo for Rent

    4660 Ocean Blvd Unit Q, Sarasota, FL 34242

    FULL GULF & SUNSET VIEWS | TURNKEY FURNISHED | WALK TO SIESTA VILLAGE & BEACHSeasonal rental available for January, February and March of 2027. Taxes are not included in the rent. Two small dogs allowed!You will be WOWED by the breathtaking full Gulf and sunset views from this TURNKEY FURNISHED Siesta Key residence! Ideally located within walking distance of the vibrant Siesta Village and

    Paul Svilokos RENTPRO MANAGEMENT LLC

    4660 Ocean Blvd Unit Q, Sarasota, FL 34242
  • 1257 S Portofino Dr Unit 38, Sarasota, FL 34242
    1257 S Portofino Dr Unit 38, Sarasota, FL 34242
    1257 S Portofino Dr Unit 38, Sarasota, FL 34242
    /96

    $4,500 Per Month

    • 2 Beds
    • 2 Baths
    • 929 Sq Ft
    • Condo for Rent

    1257 S Portofino Dr Unit 38, Sarasota, FL 34242

    Welcome to Siesta Harbor! Siesta Key Turnkey furnished ground floor 2/2 condo. Remodeled with beautiful kitchen, new stainless steel appliances, granite countertops, remodeled bathrooms and nice décor. King bed in master bedroom, two twins in second bedroom. One month minimum rental. This over 55 community is ideal for your island beach vacation. Enjoy a cocktail or your morning coffee from the

    Kay Esposito SIGNATURE REALTY ASSOCIATES

    1257 S Portofino Dr Unit 38, Sarasota, FL 34242
  • 5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242
    5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242
    5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242
    /50

    $10,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,270 Sq Ft
    • Condo for Rent

    5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242

    Welcome to your perfect Siesta Key getaway! This beautifully updated 2-bedroom, 2-bath end-unit condo in the Palm Bay Club offers stunning bay views, a bright, open interior, and resort-style amenities—just steps from the Bayfront pool. At 1,270 sq. ft., this is one of the largest condos in Palm Bay. You'll love the driftwood-style cabinetry, quartz countertops, and stainless steel appliances in

    Robert Bevington SHOWTIME REALTY

    5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242
  • 1355 S Portofino Dr Unit 103, Sarasota, FL 34242
    1355 S Portofino Dr Unit 103, Sarasota, FL 34242
    1355 S Portofino Dr Unit 103, Sarasota, FL 34242
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    $10,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,389 Sq Ft
    • Condo for Rent

    1355 S Portofino Dr Unit 103, Sarasota, FL 34242

    Discover this exceptional 2-bedroom, 2-bathroom condo, perfectly positioned for the ultimate Florida coastal escape. Step out onto your dual balconies—one on the side and one in the back—offering breathtaking, unobstructed views of the serene Intracoastal Waterway. Watch boats glide by, spot dolphins playing, and soak in the stunning views from your own private vantage points. This rarely

    Teresa Ribaudo JENNETTE PROPERTIES INC

    1355 S Portofino Dr Unit 103, Sarasota, FL 34242
  • 4822 Ocean Blvd Unit 2F, Sarasota, FL 34242
    4822 Ocean Blvd Unit 2F, Sarasota, FL 34242
    4822 Ocean Blvd Unit 2F, Sarasota, FL 34242
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    $9,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,435 Sq Ft
    • Condo for Rent

    4822 Ocean Blvd Unit 2F, Sarasota, FL 34242

    Gulf Views!!Siesta Key! This captivating 2-bedroom, 2-bathroom condominium is found in Siesta Towers in Siesta Key and is close to restaurants and outdoor recreation. The complex is an easy pedestrian distance to Siesta Key Village, and convenient to Siesta Key Beach. The interior welcomes you with stylish fixtures blending seamlessly with bounteous window light and neutral decor. The large

    Jane Hunter JENNETTE PROPERTIES INC

    4822 Ocean Blvd Unit 2F, Sarasota, FL 34242
  • 1364 Siesta Bayside Dr Unit 1364C, Sarasota, FL 34242
    1364 Siesta Bayside Dr Unit 1364C, Sarasota, FL 34242
    1364 Siesta Bayside Dr Unit 1364C, Sarasota, FL 34242
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    $8,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    1364 Siesta Bayside Dr Unit 1364C, Sarasota, FL 34242

    Embrace coastal living in this inviting 2-bedroom, 2-bathroom first-level condo nestled within the prestigious Gulf & Bay Club Bayside in Siesta Key, Florida. Step inside to discover a thoughtfully designed space adorned with coastal-inspired décor and an abundance of natural light. The open-concept layout seamlessly connects the living, dining, and kitchen areas, creating an ideal space for

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1364 Siesta Bayside Dr Unit 1364C, Sarasota, FL 34242
  • 1250 N Portofino Dr Unit 102, Sarasota, FL 34242
    1250 N Portofino Dr Unit 102, Sarasota, FL 34242
    1250 N Portofino Dr Unit 102, Sarasota, FL 34242
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    $4,500 Per Month

    • 2 Beds
    • 2 Baths
    • 929 Sq Ft
    • Condo for Rent

    1250 N Portofino Dr Unit 102, Sarasota, FL 34242

    Available April 1, 2027! Beautiful two bedroom, two bath spacious condo. Furnished lanai with view of the Harbor and the Intracoastal Waterway - rarely available! Fifty-five+ community. Easy walk to deeded beach access to Siesta Key, the Number One Beach in the Country! Heated Outdoor Pool and Spa, Saunas, Modern Clubhouse, Patio Seating Area on the canal and our own Siesta Harbor Fishing Pier.

    Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

    1250 N Portofino Dr Unit 102, Sarasota, FL 34242
  • 1339 Siesta Bayside Dr Unit 1339C, Sarasota, FL 34242
    1339 Siesta Bayside Dr Unit 1339C, Sarasota, FL 34242
    1339 Siesta Bayside Dr Unit 1339C, Sarasota, FL 34242
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    $9,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    1339 Siesta Bayside Dr Unit 1339C, Sarasota, FL 34242

    Welcome to your elevated sanctuary in paradise – a second-floor two-bedroom condo at Gulf & Bay Bayside on the enchanting Siesta Key, Florida. Upon entering, you're immediately greeted by an open-concept living space that seamlessly integrates the interior with the scenic beauty beyond. The living area, adorned with coastal-inspired décor, invites you to relax in comfort while large

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1339 Siesta Bayside Dr Unit 1339C, Sarasota, FL 34242
  • 1313 Siesta Bayside Dr Unit 1313D, Sarasota, FL 34242
    1313 Siesta Bayside Dr Unit 1313D, Sarasota, FL 34242
    1313 Siesta Bayside Dr Unit 1313D, Sarasota, FL 34242
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    $7,600 Per Month

    • 2 Beds
    • 1 Bath
    • 959 Sq Ft
    • Condo for Rent

    1313 Siesta Bayside Dr Unit 1313D, Sarasota, FL 34242

    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

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1313 Siesta Bayside Dr Unit 1313D, Sarasota, FL 34242
  • 1241 Siesta Bayside Dr Unit 1241A, Sarasota, FL 34242
    1241 Siesta Bayside Dr Unit 1241A, Sarasota, FL 34242
    1241 Siesta Bayside Dr Unit 1241A, Sarasota, FL 34242
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    $9,300 Per Month

    • 2 Beds
    • 2 Baths
    • 1,130 Sq Ft
    • Condo for Rent

    1241 Siesta Bayside Dr Unit 1241A, Sarasota, FL 34242

    Relax in this spacious two bedroom / two bathroom vacation rental. This condo is turnkey furnished including washer / dryer and private garage. Guests are walking distance away from private, walking 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.

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1241 Siesta Bayside Dr Unit 1241A, Sarasota, FL 34242
  • 6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242
    6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242
    6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242
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    $5,000 Per Month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242

    Beachfront Bliss at Casa Mar – Siesta Key Dreaming of a Siesta Key getaway? Welcome to Unit 15 at Casa Mar, a charming 1BR/1BA beachfront condo that offers the perfect mix of relaxation and resort-style fun. Step outside and enjoy exclusive access to Casa Mar’s private stretch of quartz-whit e sand, complete with lounge chairs for sunbathing and unforgettable Gulf views. Cool off with a swim in

    Robert Bevington SHOWTIME REALTY

    6006 Midnight Pass Rd Unit 16, Sarasota, FL 34242
  • 1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
    1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
    1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
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    $9,300 Per Month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242

    Enjoy all the Siesta Key and Gulf and Bay Club Bayside amenities while staying in this spacious two-bedroom/two-bathroom vacation rental condo. The condo offers a relaxing lake, pool and tennis court view from the lanai. A few of your amenities include your own private garage, a washer and dryer IN THE CONDO, and a fully-equipped kitchen The community offers BBQ grills (6), two tennis courts,

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1226 Siesta Bayside Dr Unit 1226C, Sarasota, FL 34242
  • 1055 W Peppertree Dr Unit 506AA, Sarasota, FL 34242
    1055 W Peppertree Dr Unit 506AA, Sarasota, FL 34242
    1055 W Peppertree Dr Unit 506AA, Sarasota, FL 34242
    /31

    $7,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,163 Sq Ft
    • Condo for Rent

    1055 W Peppertree Dr Unit 506AA, Sarasota, FL 34242

    Only steps from the beautiful Crescent Beach. This luxurious 2 bedroom and 2 full bathroom unit has it all. The condo is in a Gulf-side High-rise building on the 5th floor. Assigned covered parking located in the parking garage under the building.A luxurious dining area greets you as you enter, that flows through to the living room and out to the lanai. The lanai works as an extended living

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1055 W Peppertree Dr Unit 506AA, Sarasota, FL 34242
  • 1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242
    1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242
    1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242
    /27

    $12,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,495 Sq Ft
    • Condo for Rent

    1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242

    Enjoy your vacation on Siesta Key in this spacious three bedroom / two bathroom vacation rental. 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.

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242
  • 1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242
    1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242
    1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242
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    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,130 Sq Ft
    • Condo for Rent

    1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242

    Welcome to your slice of paradise in Gulf & Bay Club Bayside, a highly sought-after community located on beautiful Siesta Key, Florida. Professionally managed by Gulf Coast Vacation rentals, this first-floor 2-bedroom, 2-bathroom lakefront condo offers the perfect blend of coastal charm and resort-style living. From the moment you step inside, you’ll be greeted by a beachy, relaxed vibe that

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1291 Siesta Bayside Dr Unit 1291A, Sarasota, FL 34242

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