Contact One Click Broker
Contacting One Click Broker
  • All fields are required.
Schedule A Showing
Schedule a Showing.
  • All fields are required.
Check this box to Register with us:
Submit an Offer Now!
Submit an Offer Now!
All fields are required.
Print Flyer
5577 Contento Drive, SARASOTA, FL 34242
  1. Image 1 of 41 For 5577 Contento Drive
  2. Image 2 of 41 For 5577 Contento Drive
  3. Image 3 of 41 For 5577 Contento Drive
  4. Image 4 of 41 For 5577 Contento Drive
  5. Image 5 of 41 For 5577 Contento Drive
  6. Image 6 of 41 For 5577 Contento Drive
  7. Image 7 of 41 For 5577 Contento Drive
  8. Image 8 of 41 For 5577 Contento Drive
  9. Image 9 of 41 For 5577 Contento Drive
  10. Image 10 of 41 For 5577 Contento Drive
  11. Image 11 of 41 For 5577 Contento Drive
  12. Image 12 of 41 For 5577 Contento Drive
  13. Image 13 of 41 For 5577 Contento Drive
  14. Image 14 of 41 For 5577 Contento Drive
  15. Image 15 of 41 For 5577 Contento Drive
  16. Image 16 of 41 For 5577 Contento Drive
  17. Image 17 of 41 For 5577 Contento Drive
  18. Image 18 of 41 For 5577 Contento Drive
  19. Image 19 of 41 For 5577 Contento Drive
  20. Image 20 of 41 For 5577 Contento Drive
  21. Image 21 of 41 For 5577 Contento Drive
  22. Image 22 of 41 For 5577 Contento Drive
  23. Image 23 of 41 For 5577 Contento Drive
  24. Image 24 of 41 For 5577 Contento Drive
  25. Image 25 of 41 For 5577 Contento Drive
  26. Image 26 of 41 For 5577 Contento Drive
  27. Image 27 of 41 For 5577 Contento Drive
  28. Image 28 of 41 For 5577 Contento Drive
  29. Image 29 of 41 For 5577 Contento Drive
  30. Image 30 of 41 For 5577 Contento Drive
  31. Image 31 of 41 For 5577 Contento Drive
  32. Image 32 of 41 For 5577 Contento Drive
  33. Image 33 of 41 For 5577 Contento Drive
  34. Image 34 of 41 For 5577 Contento Drive
  35. Image 35 of 41 For 5577 Contento Drive
  36. Image 36 of 41 For 5577 Contento Drive
  37. Image 37 of 41 For 5577 Contento Drive
  38. Image 38 of 41 For 5577 Contento Drive
  39. Image 39 of 41 For 5577 Contento Drive
  40. Image 40 of 41 For 5577 Contento Drive
  41. Image 41 of 41 For 5577 Contento Drive
Property Photos
5577 Contento Drive
Image Gallery
Would you like to sell your home before you purchase this one?
Priced at Only: $5,000
For more Information Call:
Address: 5577 Contento Drive, SARASOTA, FL 34242
Property Location and Similar Properties
All
Similar
  1. Image 1 of 41 For 5577 Contento Drive
  2. Image 2 of 41 For 5577 Contento Drive
  3. Image 3 of 41 For 5577 Contento Drive
  4. Image 4 of 41 For 5577 Contento Drive
  5. Image 5 of 41 For 5577 Contento Drive
  6. Image 6 of 41 For 5577 Contento Drive
  7. Image 7 of 41 For 5577 Contento Drive
  8. Image 8 of 41 For 5577 Contento Drive
  9. Image 9 of 41 For 5577 Contento Drive
  10. Image 10 of 41 For 5577 Contento Drive
  11. Image 11 of 41 For 5577 Contento Drive
  12. Image 12 of 41 For 5577 Contento Drive
  13. Image 13 of 41 For 5577 Contento Drive
  14. Image 14 of 41 For 5577 Contento Drive
  15. Image 15 of 41 For 5577 Contento Drive
  16. Image 16 of 41 For 5577 Contento Drive
  17. Image 17 of 41 For 5577 Contento Drive
  18. Image 18 of 41 For 5577 Contento Drive
  19. Image 19 of 41 For 5577 Contento Drive
  20. Image 20 of 41 For 5577 Contento Drive
  21. Image 21 of 41 For 5577 Contento Drive
  22. Image 22 of 41 For 5577 Contento Drive
  23. Image 23 of 41 For 5577 Contento Drive
  24. Image 24 of 41 For 5577 Contento Drive
  25. Image 25 of 41 For 5577 Contento Drive
  26. Image 26 of 41 For 5577 Contento Drive
  27. Image 27 of 41 For 5577 Contento Drive
  28. Image 28 of 41 For 5577 Contento Drive
  29. Image 29 of 41 For 5577 Contento Drive
  30. Image 30 of 41 For 5577 Contento Drive
  31. Image 31 of 41 For 5577 Contento Drive
  32. Image 32 of 41 For 5577 Contento Drive
  33. Image 33 of 41 For 5577 Contento Drive
  34. Image 34 of 41 For 5577 Contento Drive
  35. Image 35 of 41 For 5577 Contento Drive
  36. Image 36 of 41 For 5577 Contento Drive
  37. Image 37 of 41 For 5577 Contento Drive
  38. Image 38 of 41 For 5577 Contento Drive
  39. Image 39 of 41 For 5577 Contento Drive
  40. Image 40 of 41 For 5577 Contento Drive
  41. Image 41 of 41 For 5577 Contento Drive
Request More Information
  • All fields are required.
More Like This
  • MLS#: A4607468 ( Residential Lease )
  • Street Address: 5577 Contento Drive
  • Viewed: 217
  • Price: $5,000
  • Price sqft: $2
  • Waterfront: Yes
  • Wateraccess: Yes
  • Waterfront Type: Canal - Saltwater
  • Year Built: 1969
  • Bldg sqft: 2089
  • Bedrooms: 2
  • Total Baths: 2
  • Full Baths: 2
  • Days On Market: 605
  • Additional Information
  • Geolocation: 27.2692 / -82.5498
  • County: SARASOTA
  • City: SARASOTA
  • Zipcode: 34242
  • Subdivision: Siesta Isles
  • Provided by: ASCENDIA REAL ESTATE
  • Contact: Beth Dilley
  • 941-306-4242
  • mfrmls
  • DMCA Notice
  • Description
    This is a short term rental. Listing reflects off season rate. Available peak season month: January 3rd 31st, 2026. Welcome to Bikini Tini Time! Your completely remodeled Siesta Key paradise awaits in this 2 bedroom, 2 bathroom saltwater pool home, perfectly situated on a peaceful canal. We're delighted to be dog friendly, offering a fantastic space for everyone. Step inside to a meticulously designed interior with thoughtful updates throughout, from the brand new kitchen to the spa like bathrooms. You'll find a designated office space off the kitchen, perfect for remote work. The first bedroom features a king bed, and the second bedroom features a queen bed. Outside, soak up the Florida sunshine by the sparkling saltwater pool. With direct canal access, cast a line for some fishing, or launch a paddle board and explore the tranquil canals, where you're likely to spot local manatees and other fascinating wildlife. After exploring the canals, take a leisurely walk of just a few minutes to the world famous Siesta Key Beach. Feel the soft, powdery quartz sand between your toes and bask in the beauty of the Gulf. Then, it's back to your private oasis where, as the sun begins its descent, it's 'tini time! Mix your favorite martini and savor it while watching the spectacular sunset paint the sky over the canal, beautifully highlighting silhouetted palm trees. It's truly an unforgettable end to a perfect day! Bikini Tini Time offers the perfect blend of tranquility and convenience, just moments from Siesta Key Village's vibrant shops and restaurants. Pet Policy: We're delighted to welcome your furry family members! This property is pet friendly, and a non refundable pet fee (per pet) will be applied after booking and must be paid prior to check in. Please feel free to inquire about the specific pet policy applicable to your reservation.
Payment Calculator
  •   Principal & Interest -
  •   Property Tax $
  •   Home Insurance $
  •   HOA Fees $
  •   Mortgage Insurance-
  •   Monthly -
Features
Building and Construction
  • Covered Spaces: 0.00
  • Living Area: 1424.00
Garage and Parking
  • Garage Spaces: 0.00
  • Open Parking Spaces: 0.00
  • Parking Features: Driveway
Eco-Communities
  • Pool Features: In Ground
Utilities
  • Carport Spaces: 0.00
  • Cooling: Central Air
  • Heating: Central, Electric
  • Pets Allowed: Breed Restrictions, Number Limit, Size Limit, Yes
Finance and Tax Information
  • Home Owners Association Fee: 0.00
  • Insurance Expense: 0.00
  • Net Operating Income: 0.00
  • Other Expense: 0.00
Rental Information
  • Tenant Pays: Cleaning Fee
Other Features
  • Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
  • Association Name: N/A
  • Country: US
  • Furnished: Turnkey
  • Interior Features: Ceiling Fans(s), Eat-in Kitchen, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Thermostat, Walk-In Closet(s), Window Treatments
  • Levels: One
  • Area Major: 34242 - Sarasota/Crescent Beach/Siesta Key
  • Occupant Type: Tenant
  • Parcel Number: 0082160017
  • View: Water
  • Views: 217
Owner Information
  • Owner Pays: Electricity, Grounds Care, Internet, Pest Control, Pool Maintenance, Sewer, Trash Collection, Water
Similar Properties

Details for 6005 Midnight Pass Road S4, SARASOTA, FL 34242
$6,000.00 ($4.96 / sqft )

6005 Midnight Pass Road S4 More Like This

Welcome to your bright and inviting Siesta Key vacation retreat! Enjoy deeded beach access to the stunning Siesta Key Beach, just steps away, where sun and surf await. Relax by Siesta Keys largest hea

  1. Request Information
  1. Bedrooms: 2
  2. Baths: 2
  3. Approx. 1210 sqft
  4. Approx. 2.64 acres
  1. MLSID: A4660901
  2. Provided by CONCESSION REAL ESTATE COMP.
  3. Contact Susan Saltalamacchia
  4. mfrmls
  5. DMCA Notice
34 Pictures and Information
Details for 1203 Lyric Lane, SARASOTA, FL 34242
$4,950.00 ($1.64 / sqft )

1203 Lyric Lane Virtual Tour More Like This

**LEASE PURCHASE OPTION**. Bring your RV, boat, and car collectionthis updated single story home on a 17,000+ sq ft lot offers exceptional flexibility with no HOA restrictions. Interior upgrades inclu

  1. Request Information
  1. Bedrooms: 2
  2. Baths: 2
  3. Approx. 3020 sqft
  1. MLSID: A4656825
  2. Provided by FINE PROPERTIES
  3. Contact Tracy Srodes
  4. mfrmls
  5. DMCA Notice
56 Pictures and Information
Details for 735 Birdsong Lane, SARASOTA, FL 34242
$5,000.00 ($1.80 / sqft )

735 Birdsong Lane Virtual Tour More Like This

Looking for the ultimate Siesta Key getaway? This stunning 3 bedroom, 2 bath home offers everything you need for a dream vacation, just 1 mile from the famous Siesta Key Beach and a quick bike ride to

  1. Request Information
  1. Bedrooms: 3
  2. Baths: 2
  3. Approx. 2784 sqft
  1. MLSID: A4660352
  2. Provided by TNG PROPERTY MANAGEMENT
  3. Contact Scott Nold
  4. mfrmls
  5. DMCA Notice
45 Pictures and Information
Details for 5770 Midnight Pass Road 405, SARASOTA, FL 34242
$4,995.00 ($3.41 / sqft )

5770 Midnight Pass Road 405 Virtual Tour More Like This

Immaculate well maintained 2 beds 2 bath condo situated in the desirable Gulf & Bay Club on Siesta Key. This 4th floor unit is meticulously maintained and tastefully decorated. Amenities include three

  1. Request Information
  1. Bedrooms: 2
  2. Baths: 2
  3. Approx. 1466 sqft
  1. MLSID: A4644677
  2. Provided by CASEY REALTY CORPORATION
  3. Contact Pamala Casey
  4. mfrmls
  5. DMCA Notice
30 Pictures and Information
Details for 4660 Ocean Boulevard Q2, SARASOTA, FL 34242
$6,000.00 ($0.03 / sqft )

4660 Ocean Boulevard Q2 Virtual Tour More Like This

Available January through April, this stylishly furnished 2 bedroom, 2 bath Siesta Key condo offers an effortless blend of modern comfort and laid back coastal living. Located just moments from Siesta

  1. Request Information
  1. Bedrooms: 2
  2. Baths: 2
  3. Approx. 184170 sqft
  4. Approx. 4.20 acres
  1. MLSID: A4666437
  2. Provided by RANCH REALTY
  3. Contact Kevin Bryceland
  4. mfrmls
  5. DMCA Notice
22 Pictures and Information
Details for 1250 Portofino Drive 303, SARASOTA, FL 34242
$5,700.00 ($6.14 / sqft )

1250 Portofino Drive 303 Virtual Tour Reduced More Like This

Available for season 2026! Welcome to Coastal Living at its finest, perfectly nestled on the sought after barrier island of Siesta Key. Updated unit offers serene water views, abundant natural light a

  1. Request Information
  1. Bedrooms: 2
  2. Baths: 2
  3. Approx. 929 sqft
  4. Approx. 3.12 acres
  1. MLSID: A4672238
  2. Provided by MONARCH PROPERTY GROUP LLC
  3. Contact Angela Bailey
  4. mfrmls
  5. DMCA Notice
63 Pictures and Information
Details for 4946 Commonwealth Drive, SARASOTA, FL 34242
$5,000.00 ($1.90 / sqft )

4946 Commonwealth Drive More Like This

Short Term Rental Not available January April of 2026 Discover your perfect slice of "Island Time" at Just Breathe, a serene 3 bedroom, 2.5 bathroom home nestled directly on a peaceful Siesta Key c

  1. Request Information
  1. Bedrooms: 3
  2. Baths: 3
  3. Approx. 2628 sqft
  1. MLSID: A4657231
  2. Provided by ASCENDIA REAL ESTATE
  3. Contact Beth Dilley
  4. mfrmls
  5. DMCA Notice
55 Pictures and Information
Details for 357 Tierra Mar Lane 5, SARASOTA, FL 34242
$6,000.00 ($2.02 / sqft )

357 Tierra Mar Lane 5 Virtual Tour More Like This

Siesta Key Furnished Annual or Seasonal Rental (4 month minimum). You will love living in this quiet enclave of 6 homes, tucked away from all of the hustle and bustle but walkable to all of the many d

  1. Request Information
  1. Bedrooms: 3
  2. Baths: 3
  3. Approx. 2970 sqft
  1. MLSID: A4663497
  2. Provided by PREMIER SOTHEBY'S INTERNATIONAL REALTY
  3. Contact Alex Lane
  4. mfrmls
  5. DMCA Notice
77 Pictures and Information
Details for 8710 Midnight Pass Road 203, SARASOTA, FL 34242
$6,000.00 ($3.64 / sqft )

8710 Midnight Pass Road 203 Virtual Tour More Like This

Nestled in a serene spot on Turtle Beach, this charming condo offers the perfect blend of coastal living and comfort. With breathtaking views its an ideal spot for relaxation or adventure. The cond

  1. Request Information
  1. Bedrooms: 2
  2. Baths: 2
  3. Approx. 1650 sqft
  4. Approx. 3.31 acres
  1. MLSID: A4665996
  2. Provided by PRECISE REALTY CORP
  3. Contact Jennifer LeBlanc
  4. mfrmls
  5. DMCA Notice
41 Pictures and Information
Details for 8735 Midnight Pass Road 206b, SARASOTA, FL 34242
$6,000.00 ($4.08 / sqft )

8735 Midnight Pass Road 206b Virtual Tour Reduced More Like This

Owner is highly motivated! Looking for a sunny escape from the winter chill? Welcome to your fully furnished 3 MONTH seasonal rental in the sought after Turtle Bay community on Siesta Key, just minute

  1. Request Information
  1. Bedrooms: 2
  2. Baths: 2
  3. Approx. 1472 sqft
  1. MLSID: A4667149
  2. Provided by KW COASTAL LIVING III
  3. Contact Justin Piccillo
  4. mfrmls
  5. DMCA Notice
57 Pictures and Information
Nearby Subdivisions
Anchorage   Bay Oaks   Bay Tree Club   Beachway Apts   Boca Siesta   Casa Mar   Coquille   Gulf Bay Club   Gulf Bay Club Bayside   Gulf Bay Club Ph 2   Gulf Bay Club Ph 3   Gulf Bay Club Ph 6   Harbor Towers Y R   Harbour Towne   Harmony Sub   Inlet Apts   Island Reef   Island Reef I   Island Reef Ii Ph 1 2 3   Jamaica Royale   Lands End   Midnight Cove Ii   Midnight Sea   Palm Bay Club Ii   Paradise Island   Peppertree Bay Ii   Point Of Rocks Terrace   Pointe On Midnight Pass   Polynesian Gardens   Provincial Gardens   Riegels Landing   Sanderling Club   Sandy Cove   Sandy Cove Ii   Sandy Cove Iv   Sandy Hook   Sarasota Beach   Sea Village   Sea Village Siesta Key   Siesta Beach   Siesta Breakers   Siesta Harbor I   Siesta Harbor Ii   Siesta Harbor Sec 2   Siesta Isles   Siesta Key Beach Residences Ii   Siesta Manor Sec 1   Siesta Manor Sec 2   Siesta Manor Sec 3   Siesta Towers   Siestas Bayside Waterside Sout   Somerset Cay   Spindrift   Sunrise Cove Sec 2   Terrace   Tortoise Estates   Tortuga   Turtle Bay   Turtle Bay Sec 1   Twin Banyan   Village Place   Vista Hermosa   Whispering Sands Sec 5   Whispering Sands Sec 6   Whispering Sands Sec 7  
Skip to Main Content
  1. One Click Broker
  2. 800.557.8193
  3. Toll Free: 800.557.8193
  4. billing@brokeridxsites.com