106

Siesta Key, FL Condos for Rent with Community Pool

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  • /49

    $9,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,489 Sq Ft
    • Condo for Rent

    6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242

    ***AVAILABLE MAY 2026*** one MONTH MIN***Welcome to the Beach! Prime Siesta Key location. This large, spacious 2 Bedroom/2 Bath split floor plan condo comes with a full-length balcony with views of the gulf and intracoastal waterway, as well as the beautiful sunsets. Available as a monthly rental, the interior boasts a decorative fireplace, reclining sofa, two walk-in closets, washer and dryer in

    Agent Photo

    Anthony DeLuca

    AUDREY RAIN RENTALS, INC

    (941) 271-7125

    6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
  • /20

    $4,900 Per Month

    • 1 Bed
    • 1 Bath
    • 1,040 Sq Ft
    • Condo for Rent

    5860 Midnight Pass Rd Unit 40, Sarasota, FL 34242

    Property Id: 2528213Experience the best of coastal living in this beautifully appointed beachside residence located within the highly desirable Siesta Key community of Gulf Haven. Perfectly positioned just steps from the sugar-white sands and turquoise waters of the Gulf, this charming 1-bedroom, 1-bathroom condo offers the relaxed luxury and island lifestyle that makes Siesta Key one of

    (941) 404-7666

    5860 Midnight Pass Rd Unit 40, Sarasota, FL 34242
  • /27

    $8,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,455 Sq Ft
    • Condo for Rent

    1195 Coquille St Unit 309, Sarasota, FL 34242

    Beautiful 2 Bedroom 2 Bathroom Townhome available! Come see this gorgeous home ready for you to call home! Large living spaces including full kitchen, living room and dining room, 3 seasons room and loft area. Loft area ideal for office space or second floor den. Two large bedrooms including plenty of closet and storage space. Nice patio with grill to enjoy evenings and entertaining. Large full

    Agent Photo

    Anna Fattore

    COMPASS FLORIDA LLC

    (941) 390-0370

    1195 Coquille St Unit 309, Sarasota, FL 34242
  • /26

    $3,000

    Total Monthly Price

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

    5683 Midnight Pass Rd Unit 105, Siesta Key, FL 34242

    5683 Midnight Pass Rd Unit 105, Siesta Key, FL 34242
  • /50

    $6,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,260 Sq Ft
    • Condo for Rent

    5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242

    RARE OPPORTUNITY to RENT THE PENTHOUSE. 3 BEDS/2.5 BATHS full size washer/dryer and a roof top deck with panoramic views available September 2025 stay for a year, 2 or 3+ owner wants this beautiful turnkey home with a BOAT DOCK (no lift yet)RENTED LONG TERM. Owner open to lift discussion. You will enjoy Penthouse end unit in Boca Siesta is located in the heart of Siesta Key the #1 Beach in the

    Agent Photo

    Marianne LeBar

    ROSEBAY INTERNATIONAL REALTY, INC

    (941) 213-8487

    5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242
  • /63

    $15,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 3,524 Sq Ft
    • Condo for Rent

    1308 Old Stickney Point Rd Unit WP3, Sarasota, FL 34242

    AVAILABLE 1/4/27 Experience the pinnacle of coastal living in this exceptional penthouse at Marina Del Sol with PRIVATE 52 FT BOAT SLIP. Perfectly positioned moments from the #1-rated Siesta Key Beach. This rare residence offers panoramic Gulf of Mexico sunsets on one side and serene Bay views on the other—an unmatched indoor-outdoor lifestyle framed by water in every direction.****Designed for

    Agent Photo

    Tracy Srodes

    FINE PROPERTIES

    (941) 883-3308

    1308 Old Stickney Point Rd Unit WP3, Sarasota, FL 34242
  • /16

    $9,500 Per Month

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

    1055 W Peppertree Dr Unit 603AA, Sarasota, FL 34242

    Just steps from Crescent Beach, this unit has 2 bedrooms and 2 full bathrooms. Complete with a full kitchen supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and has a Keurig.The formal dining area has seating for 6. This flows into the living area that has comfortable couch seating, a fan, access to the lanai and a 55"

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1055 W Peppertree Dr Unit 603AA, Sarasota, FL 34242
  • /35

    $7,400 Per Month

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

    1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242

    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

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242
  • /36

    $7,500 Per Month

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

    5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242

    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

    Robert Bevington SHOWTIME REALTY

    5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242
  • /54

    $9,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,835 Sq Ft
    • Condo for Rent

    1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242

    Indulge in opulent coastal living with this luxurious 3-bedroom, 2-bathroom second-floor, two-level condo in the prestigious Gulf & Bay Club Bayside on Siesta Key, Florida. This impeccably designed residence offers a unique and spacious layout, with the primary bedroom occupying its own private floor for the utmost in privacy and elegance.As you enter, the living room, dining room, and

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1389 Siesta Bayside Dr Unit 1389F, 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
  • /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
  • /15

    $5,000 Per Month

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

    1255 E Peppertree Dr Unit 306, Sarasota, FL 34242

    2 BR - 2 BA - 6 Person Max - High-rise - Greenbelt View This property is a 30 night minimum.1255 - 306 is a Bay-side Mid-rise unit, located approximately 75 yards away from the Bay.Hardwood floors on the lanai. Assigned covered parking located in parking garage.Approx. 1250 Sq. Ft. (1375 including the lanai) Condo Summary:Bedding: Master Bedroom: King - Guest Bedroom:

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1255 E Peppertree Dr Unit 306, Sarasota, FL 34242
  • /27

    $5,200 Per Month

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

    1255 E Peppertree Dr Unit 602, Sarasota, FL 34242

    Enjoy Gulf of Mexico views from our recently renovated penthouse apartment on Siesta Key. You will have access to the #1 beach in the US with white powder sand and warm gulf waters. Enjoy beautiful views of the gulf from our full-length lanai and both bedrooms.The condominium offers multiple heated swimming pools, beach side and bay side grills, fishing pier, and a recently renovated exercise

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1255 E Peppertree Dr Unit 602, Sarasota, FL 34242
  • /41

    $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
  • /72

    $5,000 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
  • /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
  • /30

    $3,500 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 May through December 2026! 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 glass lanai,

    Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

    1215 S Portofino Dr Unit 308, Sarasota, FL 34242
  • /76

    $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 Keyplus 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

    Robert Bevington SHOWTIME REALTY

    1700 Cove II Place Unit 310, Sarasota, FL 34242
  • /49

    $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

    Robert Bevington SHOWTIME REALTY

    5963 Midnight Pass Rd Unit 332, Sarasota, FL 34242
  • /22

    $8,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,319 Sq Ft
    • Condo for Rent

    6044 W Peppertree Way Unit 233B, Sarasota, FL 34242

    This property is a 30 night minimum. Welcome to your perfect vacation retreat! This beautifully appointed 3-bedroom, 2-bathroom condo offers the ideal blend of comfort, style, and convenience. Situated in a prime location, this property provides the perfect base for your getaway, whether you’re seeking relaxation, adventure, or a little of both. Step inside to find a spacious open-concept living

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6044 W Peppertree Way Unit 233B, 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
  • /36

    $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
  • /37

    $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

    Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

    1215 S Portofino Dr Unit 202, 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
  • /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
  • /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
  • /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

    Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

    1250 N Portofino Dr Unit 302, Sarasota, FL 34242
  • /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
  • /15

    $8,000 Per Month

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

    460 Beach Rd Unit A1, Sarasota, FL 34242

    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

    Brenda Cozy COLDWELL BANKER REALTY

    460 Beach Rd Unit A1, 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
  • /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
  • /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
  • /31

    $8,900 Per Month

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

    1055 W Peppertree Dr Unit 302AA, Sarasota, FL 34242

    Only steps from the beautiful Crescent Beach. This luxurious 2 bedroom and 2 full bathroom unit has it all. The unit is in a Gulfside Highrise building on the 3rd floor. The kitchen has been renovated with stainless steel appliances and is supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and has a Keurig. The master bedroom

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1055 W Peppertree Dr Unit 302AA, Sarasota, FL 34242
  • /67

    $3,350 Per Month

    • 2 Beds
    • 2 Baths
    • 1,498 Sq Ft
    • Condo for Rent

    5880 Midnight Pass Rd Unit 306, Sarasota, FL 34242

    Available April 2026 and Beyond! The rate shown reflects the annual rental price. Seasonal rates for April 2026 may vary. Don’t miss the opportunity to secure this property, reach out for availability and details. Step into paradise at Casarina, a beautifully maintained beachfront community right on Siesta Key’s world-famous Crescent Beach. With 200 feet of private beach access, you’re just steps

    Cole Collins COLDWELL BANKER REALTY

    5880 Midnight Pass Rd Unit 306, Sarasota, FL 34242
  • /65

    $6,000 Per Month

    • 1 Bed
    • 1.5 Baths
    • 928 Sq Ft
    • Condo for Rent

    5400 Ocean Blvd Unit 5-3, Sarasota, FL 34242

    SEASONAL OR ANNUAL RENTAL AVAILABLE AT BEACH TERRACE ON SIESTA KEY! Experience Siesta Key beachfront living at it’s best in this beautifully renovated, fifth-floor corner condo directly on world-renowned Siesta Beach, ranked #1 in the U.S. This turnkey furnished 1-bedroom, 1.5-bath retreat features floor-to-ceiling impact sliding glass doors opening to three private balconies, creating over 1,280

    Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

    5400 Ocean Blvd Unit 5-3, 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
  • /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
  • /27

    $6,900 Per Month

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

    1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242

    Spacious one bedroom/one bathroom vacation rental at the Gulf and Bay Club Bayside on the island paradise of Siesta Key just offshore of Sarasota, Florida. Private access to Crescent Beach on the Gulf of Mexico - just steps to the beach. Free high-speed Internet connection. Please note the garage for this unit is the middle garage in the building to the right.*Taxes and Fees not included.

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242
  • /23

    $8,050 Per Month

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

    6053 E Peppertree Way Unit 118, Sarasota, FL 34242

    This property is a 30 night minimum. This unit has been completely renovated and offers spectacular views of the Intracoastal waterway and pier! The sliders to the lanai open to the screened-in area for fresh air and seamless indoor/outdoor living.The unit offers easy access to the walking paths that leads to the fishing pier and to the bay-side pool and clubhouse.This condo has 2

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6053 E Peppertree Way Unit 118, Sarasota, FL 34242

Showing Results 1 - 40, Page 1 of 3

Rental Home Trends in Siesta Key, FL

Rental Home Trends

Number of Condos for Rent
106
Median Condo Rent
$4,500
Median 2 Bedroom Condo Rent
$4,500
How to Rent a Home