124

Condos for Rent in ZIP Code 34242

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  • 1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242
    1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242
    1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242
    /35

    $8,200 per month

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

    1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242

    Welcome to your coastal retreat at Gulf & Bay Club Bayside in Siesta Key, Florida! Nestled on the second level, this 2-bedroom, 2-bathroom condo offers a perfect blend of comfort and breathtaking views of the bay and boat slip.As you step into this meticulously designed space, you'll immediately be drawn to the open-concept living area bathed in natural light. The coastal vibes are

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242
  • 1326 Siesta Bayside Dr Unit 1326D, Sarasota, FL 34242
    1326 Siesta Bayside Dr Unit 1326D, Sarasota, FL 34242
    1326 Siesta Bayside Dr Unit 1326D, Sarasota, FL 34242
    /27

    $6,300 per month

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

    1326 Siesta Bayside Dr Unit 1326D, Sarasota, FL 34242

    Welcome to your dream coastal retreat at Gulf & Bay Bayside in Siesta Key, Florida! Nestled within this exclusive waterfront community, this exquisite two-bedroom condo offers a perfect blend of luxurious living and breathtaking views.As you step into this meticulously designed residence, you are greeted by an open-concept living space adorned with tasteful coastal decor. The living area,

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1326 Siesta Bayside Dr Unit 1326D, Sarasota, FL 34242
  • 1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242
    1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242
    1389 Siesta Bayside Dr Unit 1389F, 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
  • 1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242
    1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242
    1338 Siesta Bayside Dr Unit 1338C, 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
  • 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
    /36

    $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
  • 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
  • 1260 Siesta Bayside Dr Unit 1260A, Sarasota, FL 34242
    1260 Siesta Bayside Dr Unit 1260A, Sarasota, FL 34242
    1260 Siesta Bayside Dr Unit 1260A, Sarasota, FL 34242
    /30

    $7,700 per month

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

    1260 Siesta Bayside Dr Unit 1260A, Sarasota, FL 34242

    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

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1260 Siesta Bayside Dr Unit 1260A, Sarasota, FL 34242
  • 1318 Siesta Bayside Dr Unit C, Siesta Key, FL 34242
    1318 Siesta Bayside Dr Unit C, Siesta Key, FL 34242
    1318 Siesta Bayside Dr Unit C, Siesta Key, FL 34242
    /24

    $4,500 per month

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

    1318 Siesta Bayside Dr Unit C, Siesta Key, FL 34242

    Enjoy our beautiful holiday retreat on Siesta Key Island, with private access to the stunning whites sands of Crescent Beach – Previously voted No. 1 beach in USA! Our 2 bed/2 bath condo located in this uniquely designed low rise ‘Key West’ style complex has ground floor access with sheltered South facing Garden – free WIFI throughout the condo. While away your lazy days on our fishing dock when

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1318 Siesta Bayside Dr Unit C, Siesta Key, 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
  • 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
  • 1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242
    1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242
    1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242
    /27

    $9,900 per month

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

    1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242

    Come and watch the dolphins and manatees on the intercoastal waterway from our lanai! This unit has 2 large bedrooms and 2 full baths. There is a washer and dryer in the unit and a garage to park your car and store all the beach equipment you will need for the beach. It's only a short 10 min. walk down the private deeded beach access to the beautiful white sands of Siesta Key beach. We share

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242
  • 1351 Siesta Bayside Dr Unit 1351D, Sarasota, FL 34242
    1351 Siesta Bayside Dr Unit 1351D, Sarasota, FL 34242
    1351 Siesta Bayside Dr Unit 1351D, Sarasota, FL 34242
    /22

    $7,200 per month

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

    1351 Siesta Bayside Dr Unit 1351D, Sarasota, FL 34242

    Relax in the spacious living area or enjoy a glass of wine on the lanai.This condo is turnkey furnished including washer /dryer and private garage. Guests are walking distance away from private beach access to Siesta Key's world-renowned white sandy beach on the Gulf of Mexico. Come stay with us and enjoy warm sunny Siesta Key!**Taxes and fees not included.

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1351 Siesta Bayside Dr Unit 1351D, 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
  • 1327 Siesta Bayside Dr Unit 1327C, Sarasota, FL 34242
    1327 Siesta Bayside Dr Unit 1327C, Sarasota, FL 34242
    1327 Siesta Bayside Dr Unit 1327C, Sarasota, FL 34242
    /21

    $9,300 per month

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

    1327 Siesta Bayside Dr Unit 1327C, Sarasota, FL 34242

    This spacious, private and light-colored 2-bedroom/2-bathroom end unit has a lanai that overlooks a lake with frequent bird sightings. Walk right out to an inland waterway and fishing dock. A large, heated pool is just across from the unit. Beach accessories as well as fishing gear and bicycles are available in the private garage.THIS CONDO REQUIRES A TWO WEEK MINIMUM

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1327 Siesta Bayside Dr Unit 1327C, 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
  • 1204 Siesta Bayside Dr Unit 1204D, Sarasota, FL 34242
    1204 Siesta Bayside Dr Unit 1204D, Sarasota, FL 34242
    1204 Siesta Bayside Dr Unit 1204D, Sarasota, FL 34242
    /26

    $6,900 per month

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

    1204 Siesta Bayside Dr Unit 1204D, Sarasota, FL 34242

    This lovely well-maintained and upgraded condo in a gated community, is located on the ground floor and offers one bedroom plus an additional den furnished as a small guest bedroom. The condo is turnkey furnished including washer /dryer and private garage, an approximate 5-minute walk, via deeded, walking access across the street, to the #1 beach in the U.S.A., Siesta Key! Choose to enjoy two

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1204 Siesta Bayside Dr Unit 1204D, 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
    /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
  • 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
    /31

    $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
  • 1360 Siesta Bayside Dr, Sarasota, FL 34242
    1360 Siesta Bayside Dr, Sarasota, FL 34242
    1360 Siesta Bayside Dr, Sarasota, FL 34242
    /30

    $7,000 per month

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

    1360 Siesta Bayside Dr, Sarasota, FL 34242

    This fabulous one bedroom, plus a full sleep-in den, provides additional space for a quiet sitting room or a guest retreat. Relax in the spacious living area or enjoy a glass of wine on the lanai.The 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

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1360 Siesta Bayside Dr, Sarasota, FL 34242
  • 1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242
    1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242
    1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242
    /31

    $9,300 per month

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

    1269 Siesta Bayside Dr Unit 1269-C, Sarasota, FL 34242

    Deeded Walking Access Directly to the Beach!New on the rental program - Beautifully updated 2-bedroom near the pool, tennis courts and path to the beach! Please be one of our first Guests!The moment you arrive at Gulf & Bay Club Bayside, you’ll appreciate the beauty, serenity, and charm of this "Key West” style village. Located on the bay across the street from world-famous Siesta

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1269 Siesta Bayside Dr Unit 1269-C, 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
    /26

    $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
  • 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
  • 1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242
    1200 Siesta Bayside Dr Unit 1200G, Sarasota, FL 34242
    1200 Siesta Bayside Dr Unit 1200G, 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
  • 8911 Midnight Pass Rd Unit 514, Sarasota, FL 34242
    8911 Midnight Pass Rd Unit 514, Sarasota, FL 34242
    8911 Midnight Pass Rd Unit 514, Sarasota, FL 34242
    /81

    $8,500 per month

    • 2 Beds
    • 2 Baths
    • 1,233 Sq Ft
    • Condo for Rent

    8911 Midnight Pass Rd Unit 514, Sarasota, FL 34242

    BOOKED FEB/APRIL 2026. AVAILABLE JANUARY 2026. UTILITIES INCLUDED. SIESTA KEY SPECTACULAR FULL BAY/INTRACOASTAL UNOBSTRUCTED VIEWS! BOOK YOUR BEACH GETAWAY NOW! Beautifully updated throughout Turnkey "top floor" Condo in this popular community of Sunrise Cove. Located on the southern end of Siesta Key, directly across the street from Turtle Beach! Upon entering the condo, you will immediately

    Chrissie Cummings JENNETTE PROPERTIES INC

    8911 Midnight Pass Rd Unit 514, Sarasota, FL 34242
  • 1350 N Portofino Dr Unit 108, Sarasota, FL 34242
    1350 N Portofino Dr Unit 108, Sarasota, FL 34242
    1350 N Portofino Dr Unit 108, Sarasota, FL 34242
    /38

    $6,500 per month

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

    1350 N Portofino Dr Unit 108, Sarasota, FL 34242

    Gorgeous Canal View Condo now available on Siesta Key as an annual rental. Rent for the remainder of 2025 through the Winter Season until December 2026 and work from home on your walk-out lanai watching the deep water boats on the Intracoastal Waterway. Incredible View of the Intracoastal Waterway, Beautiful two bedroom, two bath spacious first floor walk-out condo with lots of natural light.

    Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

    1350 N Portofino Dr Unit 108, Sarasota, FL 34242
  • 5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242
    5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242
    5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242
    /65

    $8,700 per month

    • 2 Beds
    • 2 Baths
    • 1,256 Sq Ft
    • Condo for Rent

    5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242

    Listing reflects peak season rate. Available peak season months: January 2026, April 2026. Discover Turquoise Turtle, a beautiful 2-bedroom, 2-bathroom condo nestled within the luxurious Harbor Towers Yacht & Racquet Club on Siesta Key. This charming beach palace is your true coastal getaway, offering a prime location and resort-style amenities. From the moment you park in your assigned spot,

    Beth Dilley ASCENDIA REAL ESTATE

    5855 Midnight Pass Rd Unit 426, Sarasota, FL 34242
  • 9122 Midnight Pass Rd Unit 34, Sarasota, FL 34242
    9122 Midnight Pass Rd Unit 34, Sarasota, FL 34242
    9122 Midnight Pass Rd Unit 34, Sarasota, FL 34242
    /61

    $5,000 per month

    • 3 Beds
    • 3 Baths
    • 2,558 Sq Ft
    • Condo for Rent

    9122 Midnight Pass Rd Unit 34, Sarasota, FL 34242

    Available May 1, 2026 for an annual lease! Rarely available 3 bed, 3 bath, plus office/work-space condo in sought-after Somerset Cay! You will love the resort-style amenities and the contemporary elegance this wonderful home offers. There are three balconies, offering views of the Bay, the Intercoastal Waterway and the Gulf. Fully updated kitchen with top-of-the-line appliances and breakfast bar,

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    9122 Midnight Pass Rd Unit 34, Sarasota, FL 34242
  • 116 Vista Hermosa Cir Unit 210C, Sarasota, FL 34242
    116 Vista Hermosa Cir Unit 210C, Sarasota, FL 34242
    116 Vista Hermosa Cir Unit 210C, Sarasota, FL 34242
    /51

    $7,200 per month

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

    116 Vista Hermosa Cir Unit 210C, Sarasota, FL 34242

    Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Experience the ultimate beach getaway at "Carefree Coconut," a charming second-floor corner unit located in the heart of Siesta Key's welcoming Vista Hermosa community. True to its Spanish name, "Beautiful View," this community offers a delightful escape, blending old Florida

    Beth Dilley ASCENDIA REAL ESTATE

    116 Vista Hermosa Cir Unit 210C, Sarasota, FL 34242
  • 9008 Midnight Pass Rd Unit 4, Sarasota, FL 34242
    9008 Midnight Pass Rd Unit 4, Sarasota, FL 34242
    9008 Midnight Pass Rd Unit 4, Sarasota, FL 34242
    /23

    $14,999 per month

    • 3 Beds
    • 3.5 Baths
    • 3,700 Sq Ft
    • Condo for Rent

    9008 Midnight Pass Rd Unit 4, Sarasota, FL 34242

    THE SEA BREEZE: Exclusive seasonal rental for the discerning taste. This beautiful 3 bedroom, 3 1/2 bath residence has magnificent views of Sarasota Bay and the Gulf of Mexico/ Premium space in this luxurious well-appointed and professionally designed tropical private residence, available in season January 1, 2024. Wall to wall windows spanning the 3700 feet of gracious living space will appeal

    Robin Turner WATERSIDE REALTY LLC

    9008 Midnight Pass Rd Unit 4, Sarasota, FL 34242
  • 8770 Midnight Pass Rd Unit 302B, Sarasota, FL 34242
    8770 Midnight Pass Rd Unit 302B, Sarasota, FL 34242
    8770 Midnight Pass Rd Unit 302B, Sarasota, FL 34242
    /75

    $4,000 per month

    • 2 Beds
    • 2 Baths
    • 1,286 Sq Ft
    • Condo for Rent

    8770 Midnight Pass Rd Unit 302B, Sarasota, FL 34242

    Siesta Key living just steps from the Gulf of Mexico at beautiful, tranquil Island Reef on the quiet end of the Island. Spacious 2 bedrooms, 2 baths, laundry in residence, carport, and guest parking. Tile flooring throughout the condo. Island Reef is a serene waterfront community, one of the few true Gulf to Bay properties, that offers many desirable amenities including: beach and boat docks

    Erick Shumway RE/MAX ALLIANCE GROUP

    8770 Midnight Pass Rd Unit 302B, Sarasota, FL 34242
  • 8770 Midnight Pass Rd Unit 402B, Sarasota, FL 34242
    8770 Midnight Pass Rd Unit 402B, Sarasota, FL 34242
    8770 Midnight Pass Rd Unit 402B, Sarasota, FL 34242
    /76

    $4,000 per month

    • 2 Beds
    • 2 Baths
    • 1,286 Sq Ft
    • Condo for Rent

    8770 Midnight Pass Rd Unit 402B, Sarasota, FL 34242

    Look no further than Siesta Key's "Island Reef" for your annual vacation getaway. The stunning Gulf to Bay location features the fourth-floor unit overlooking the intercostal waterway, just a short walk to the beach. The Siesta Key village and local dining are just a stroll away. The property has a beautiful community pool, tennis courts, shuffleboard, and more. The stylish decore and nicely

    Erick Shumway RE/MAX ALLIANCE GROUP

    8770 Midnight Pass Rd Unit 402B, Sarasota, FL 34242
  • 8767 Midnight Pass Rd Unit 506F, Sarasota, FL 34242
    8767 Midnight Pass Rd Unit 506F, Sarasota, FL 34242
    8767 Midnight Pass Rd Unit 506F, Sarasota, FL 34242
    /37

    $3,500 per month

    • 2 Beds
    • 2 Baths
    • 1,303 Sq Ft
    • Condo for Rent

    8767 Midnight Pass Rd Unit 506F, Sarasota, FL 34242

    Seasonal Property available on the top floor in Siesta Key, Look no further than "Island Reef" This Gulf to Bay location features the top floor PH unit directly overlooking the intercostal water way, just a short walk to the beach and very close to the Siesta key village and local dining. The property has a beautiful community pool, Tennis courts, shuffle board and much more. Entering the unit

    Lee Brewer RE/MAX ALLIANCE GROUP

    8767 Midnight Pass Rd Unit 506F, Sarasota, FL 34242
  • 20 Whispering Sands Dr Unit 903, Sarasota, FL 34242
    20 Whispering Sands Dr Unit 903, Sarasota, FL 34242
    20 Whispering Sands Dr Unit 903, Sarasota, FL 34242
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    $12,000 per month

    • 2 Beds
    • 2 Baths
    • 1,282 Sq Ft
    • Condo for Rent

    20 Whispering Sands Dr Unit 903, Sarasota, FL 34242

    Looking for the perfect vacation get-a-way with expansive views of the Gulf of Mexico? Do you long to fall asleep to the sounds of the surf? Look no further than this stunningly remodeled 2 bed, 2 bath condo in the Whispering Sands Community. This wonderful 55+ community offers you the convenience of village living but is very peaceful and private at the same time. Leave the hustle and bustle of

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    20 Whispering Sands Dr Unit 903, Sarasota, FL 34242
  • 915 Seaside Dr Unit 512, Sarasota, FL 34242
    915 Seaside Dr Unit 512, Sarasota, FL 34242
    915 Seaside Dr Unit 512, Sarasota, FL 34242
    /30

    $26,319 per month

    • 2 Beds
    • 3 Baths
    • 1,750 Sq Ft
    • Condo for Rent

    915 Seaside Dr Unit 512, Sarasota, FL 34242

    Bask in the sunshine and sit in the pristine crystal white sands on Crescent Beach, rated #1 in the country by Dr. Beach. This beachfront sanctuary offers a fitness center, heated pool, outdoor grotto style whirlpool hot tub, bicycles, kayaks and barbecue grills, the tiki bar offers food from the famous Morton’s and cabanas to shield you from the sun when you want some shade. The unit has top of

    Andy Moore GULF COAST REALTY & MANAGEMENT

    915 Seaside Dr Unit 512, 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 decor. 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
  • 5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
    5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
    5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
    /57

    $5,000 per month

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

    5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242

    Listing reflects off-season rate. Available peak season months: March 2026, April 2026. Introducing your dream beachfront getaway in Siesta Key, Florida or as we like to call it... 2 Tickets to Paradise! This stunning 2-bedroom, 2-bathroom beachfront condo offers the perfect blend of luxury and relaxation. With direct beach access and tranquil views of the garden and ocean, it's the perfect spot

    Beth Dilley ASCENDIA REAL ESTATE

    5760 Midnight Pass Rd Unit 208, Sarasota, FL 34242
  • 6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242
    6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242
    6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242
    /42

    $5,000 per month

    • 2 Beds
    • 2.5 Baths
    • 1,332 Sq Ft
    • Condo for Rent

    6157 Midnight Pass Rd Unit D32, Sarasota, FL 34242

    Variable rent based on season

    Terry Dorrity INTEGRITY INVESTMENTS REALTY

    6157 Midnight Pass Rd Unit D32, 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
    /60

    $6,500 per month

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

    1250 N Portofino Dr Unit 102, Sarasota, FL 34242

    Available January to April 1, 2026! 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

    Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

    1250 N Portofino Dr Unit 102, Sarasota, FL 34242
  • 4660 Ocean Blvd Unit B2, Sarasota, FL 34242
    4660 Ocean Blvd Unit B2, Sarasota, FL 34242
    4660 Ocean Blvd Unit B2, Sarasota, FL 34242
    /43

    $3,800 per month

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

    4660 Ocean Blvd Unit B2, Sarasota, FL 34242

    SIESTA KEY WATERFRONT UNIT AVAILABLE now until 12/20/25 and again starting April 1, 2026. Close proximity to beach. Sea Village offers million dollar views and is situated on 5 acres overlooking the Gulf. It provides a peaceful retreat with opportunities to witness breathtaking sunsets, the full moon reflecting on the water, and serene walks to the beach and Siesta Village. Additionally, its

    Margaret Young JENNETTE PROPERTIES, INC.

    4660 Ocean Blvd Unit B2, Sarasota, FL 34242
  • 5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242
    5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242
    5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242
    /42

    $8,500 per month

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

    5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242

    ** BOOKED JANUARY THROUGH MARCH 2025 ***GORGEOUS BEACHFRONT HOME LOCATED IN THE HIGHLY SOUGHT AFTER GULF & BAY COMMUNITY! Enjoy spectacular sunsets and views of the Gulf of Mexico from this 6th floor 2 Bedroom/ 2 Bath luxury condo. Full Gulf views from living room/dining room combo and master bedroom! Gulf & Bay Club is located on Siesta Key Beach, voted #1 Beach in the USA! The spacious unit

    Kayla Lamb NEXTHOME EXCELLENCE

    5770 Midnight Pass Rd Unit 605, Sarasota, FL 34242

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