119

Siesta Key, FL Homes for Rent

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  • 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
    /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
  • 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
  • 5516 Avenida Del Mare, Sarasota, FL 34242
    5516 Avenida Del Mare, Sarasota, FL 34242
    5516 Avenida Del Mare, Sarasota, FL 34242
    /60

    $15,000 per month

    • 3 Beds
    • 2 Baths
    • 2,259 Sq Ft
    • House for Rent

    5516 Avenida Del Mare, Sarasota, FL 34242

    This is a short term rental. Listing reflects peak season rate. Available peak season months: January 5th - February 6th 2026, April 2026. Unwind and Explore Siesta Key from Stylish Surf's Up! Discover the ease of being just a short walk from the renowned Siesta Key Beach while enjoying the ample space and thoughtful design of this fantastic home. Picture your family enjoying separate living

    Beth Dilley ASCENDIA REAL ESTATE

    5516 Avenida Del Mare, 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
  • 345 Avenida Leona, Sarasota, FL 34242
    345 Avenida Leona, Sarasota, FL 34242
    345 Avenida Leona, Sarasota, FL 34242
    /98

    $18,000 per month

    • 3 Beds
    • 2 Baths
    • 1,617 Sq Ft
    • House for Rent

    345 Avenida Leona, Sarasota, FL 34242

    Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Welcome to Leona's Retreat, a beautifully renovated, ground-level bungalow perfectly poised on the intercoastal canal waterway. This charming home offers the ultimate blend of peaceful island living and convenient access to all that Siesta Key has to offer. Step inside to a

    Beth Dilley ASCENDIA REAL ESTATE

    345 Avenida Leona, 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
    /46

    $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
  • 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
  • 95 Sandy Hook Rd S, Sarasota, FL 34242
    95 Sandy Hook Rd S, Sarasota, FL 34242
    95 Sandy Hook Rd S, Sarasota, FL 34242
    /14

    $30,000 per month

    • 3 Beds
    • 3 Baths
    • 3,395 Sq Ft
    • House for Rent

    95 Sandy Hook Rd S, Sarasota, FL 34242

    6 Month Minimum... Private Beach! Private Beach! Private Beach! SANDY HOOK's "BEACH-COMER COTTAGE" Available NOW!!!!!!! IN SANDY HOOK, DIRECTLY ON THE GULF AT BIG PASS. ENJOY YOUR OWN private Beach!!!TROPICAL PARADISE. SIESTA KEY'S "OUTDOOR ACADEMY"!!! ONLY 1/2 MILE AWAY! One-of-a-kind enclave of Sandy Hook at USA's No 1 BEACH. A private road takes you to Elevated living area with entry

    Joseph Russo COURTYARD MODERN

    95 Sandy Hook Rd S, 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
  • 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

    $7,500 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
  • 1250 N Portofino Dr Unit 301, Sarasota, FL 34242
    1250 N Portofino Dr Unit 301, Sarasota, FL 34242
    1250 N Portofino Dr Unit 301, Sarasota, FL 34242
    /82

    $6,500 per month

    • 2 Beds
    • 2 Baths
    • 1,123 Sq Ft
    • Condo for Rent

    1250 N Portofino Dr Unit 301, Sarasota, FL 34242

    Immaculate End Unit in the Marlin building, Ready for you to Enjoy through January 2026 and April 2026 through year-end 2026! Stunning all the way, Great Location in the complex, close to the pool, clubhouse, spa, sauna, 2 bedroom 2 full baths, enclosed lanai overlooking the canal, steps to Deeded beach access through Crescent Arms, for your pleasure daytime or sunset time! Siesta Harbor offers a

    Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

    1250 N Portofino Dr Unit 301, Sarasota, FL 34242
  • 6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
    6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
    6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
    /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
  • 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
    /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 Harbor is surrounded by the Intracoastal Waterway with Harbor and Bay views from every unit. This north facing, totally renovated 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 new coffee table, an electric fireplace, new shower heads, a portable electric grill, bikes, beach

    Margaret Young JENNETTE PROPERTIES, INC.

    1257 S Portofino Dr Unit 36, Sarasota, FL 34242
  • 1250 N Portofino Dr Unit 107, Sarasota, FL 34242
    1250 N Portofino Dr Unit 107, Sarasota, FL 34242
    1250 N Portofino Dr Unit 107, Sarasota, FL 34242
    /27

    $6,400 per month

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

    1250 N Portofino Dr Unit 107, Sarasota, FL 34242

    This 2 bedroom, 2 bath condo in this popular 55+ community, is conveniently located on the ground floor next to the club house and swimming pool, and features new appliances, granite counter tops and ceramic flooring. Queen size bed in the Master with a walk in closet plus a full wall length closet. The guest bedroom has 2 single beds that can be combined to make a King. Updated bathrooms

    Margaret Young JENNETTE PROPERTIES, INC.

    1250 N Portofino Dr Unit 107, Sarasota, FL 34242
  • 5519 Azure Way, Sarasota, FL 34242
    5519 Azure Way, Sarasota, FL 34242
    5519 Azure Way, Sarasota, FL 34242
    /25

    $12,000 per month

    • 4 Beds
    • 3 Baths
    • 2,460 Sq Ft
    • House for Rent

    5519 Azure Way, Sarasota, FL 34242

    Sprawling 4 bed. plus Waterfront/Pool/Spa home is only 4 min. to World famous Siesta Key Beach!!!Tucked away on the little "island "of Azure Way you are afforded privacy with water views . Perfect for large and/or multiple families and guests who want to enjoy either the pool or the beach without getting in the car! A brand new beautiful granite topped Kitchen space opens to a family room all

    Catherine Foley JENNETTE PROPERTIES, INC.

    5519 Azure Way, Sarasota, FL 34242

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