• Primary Photo - 5577 Contento Dr
  • Building Photo - 5577 Contento Dr
    Building Photo - 5577 Contento Dr
  • Building Photo - 5577 Contento Dr
    Building Photo - 5577 Contento Dr
$5,000 / Month

5577 Contento Dr

,

Siesta Key, FL 34242

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941-400-1322

  • Bedrooms

    2

  • Bathrooms

    2

  • Square Feet

    1,424 sq ft

  • Available

    Available Now

Highlights

  • Water access To Gulf or Ocean To Bay
  • In Ground Pool
  • Open Floorplan
  • Canal View
  • Main Floor Primary Bedroom
  • Solid Surface Countertops
5577 Contento Dr
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About This Home

Available Now

This is a short term (weekly) rental. Listing reflects off season rate. 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. MLS# A4607468

5577 Contento Dr is a house located in Sarasota County and the 34242 ZIP Code. This area is served by the Sarasota attendance zone.

* Price shown is base rent. Excludes user-selected optional fees and variable or usage-based fees and required charges due at or prior to move-in or at move-out. Price, availability, fees, and any applicable rent special are subject to change without notice.
* Square footage definitions vary. Displayed square footage is approximate.

Home Details

Home Type

Single Family Detached Home

Year Built

Built in 1969

Bedrooms and Bathrooms

Primary Bedroom on Main Walk-In Closet 2 Full Bathrooms 2 Bedrooms

Home Design

Turnkey

Interior Spaces

Open Floorplan Family Room Off Kitchen Ceiling Fan 1,424 Sq Ft Home Window Treatments

Kitchen

Solid Surface Countertops Eat-In Kitchen Solid Wood Cabinet Range Microwave Dishwasher

Laundry

Dryer Laundry in Garage Washer

Listing and Financial Details

Property Available on 8/26/25 Application Fee: 0 Assessor Parcel Number 0082160017 Tenant pays for cleaning fee The owner pays for electricity, grounds care, internet, pest control, pool maintenance, sewer, trash collection, water 1-Month Minimum Lease Term Residential Lease

Lot Details

11,400 Sq Ft Lot Property fronts a saltwater canal

Outdoor Features

Water access To Gulf or Ocean To Bay Access to Saltwater Canal Seawall

Parking

Driveway

Pool

In Ground Pool

Utilities

Thermostat Central Heating and Cooling System

Views

Canal Views

Community Details

Overview

No Home Owners Association Siesta Isles Community Siesta Isles Subdivision

Pet Policy

Breed Restrictions Pets up to 25 lbs Pet Size Limit 1 Pet Allowed $250 Pet Fee

Fees and Policies

The fees listed below are community-provided and may exclude utilities or add-ons. All payments are made directly to the property and are non-refundable unless otherwise specified.

  • One-Time Basics
    • Due at Application
      • Application Fee Per Applicant
        Charged per applicant.
        $0
    • Due at Move-In
      • Security Deposit - Refundable
        Charged per unit.
        $0

Property Fee Disclaimer: Based on community-supplied data and independent market research. Subject to change without notice. May exclude fees for mandatory or optional services and usage-based utilities.

Contact

  • Listed by Beth Dilley | ASCENDIA REAL ESTATE
  • Phone Number
  • Contact
  • Source
    Stellar MLS
Information is provided by My Florida Regional MLS DBA Stellar MLS. Information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Listing(s) information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Copyright © 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved.
Location Get Directions
| Edit
Edit Commute

Under 30 minutes

Commute Time is calculated at rush hour.
City - Siesta Key

Award-winning white-sand beaches meet laid-back island village living on Florida's Gulf Coast in Siesta Key, a barrier island stretching eight miles between Roberts Bay and the Gulf of Mexico. Daily life here carries a year-round vacation feel, from mornings on the shore to evenings wandering Ocean Boulevard in the lively Siesta Key Village district on the north end of the island. That walkable strip packs shops, restaurants, and nightlife into a compact stretch, while quieter pockets toward the south end offer a more residential pace.

The rental landscape skews toward coastal construction: elevated single-family homes, Gulf-view condominiums, and low-rise apartment communities designed around island living. Many units offer direct water access or proximity to the beach, and the small scale of the island means almost everything is within a short drive or walk.

Learn more about living in Siesta Key 
Amenities
  • Views
  • Waterfront
  • Pool
Education
Colleges & Universities Distance
Colleges & Universities Distance
Ringling Coll. of Art & Design
Drive: 19 min 8.7 mi
New College of Florida
Drive: 23 min 10.4 mi
SCF, Sarasota, Bradentown
Drive: 32 min 15.5 mi
SCF, Sarasota, Lakewood Ranch
Drive: 31 min 18.2 mi
5577 Contento Dr is within 19 minutes or 8.7 miles from Ringling Coll. of Art & Design. It is also near New College of Florida and SCF, Sarasota, Bradentown.
Schools
Phillippi Shores Elementary School
Public Elementary School
Grades PK-5
673 Students
Attendance Zone
GreatSchools rating: 9 out of 10
Ese Special Programs
Public Elementary, Middle & High School
Grades PK-12
7 Students
Nearby
Brookside Middle School
Public Middle School
Grades 6-8
674 Students
Attendance Zone
GreatSchools rating: 6 out of 10
Sarasota High School
Public High School
Grades 9-12
2,307 Students
Attendance Zone
GreatSchools rating: 5 out of 10
Out Of Door Academy-Upper School
Private Elementary, Middle & High School
Grades PK-12
709 Students
Nearby
School data provided by GreatSchools The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.

View GreatSchools Rating Methodology

Data provided by GreatSchools.org © 2026. All rights reserved.
Transportation

5577 Contento Dr is near Sarasota/Bradenton International, located 11.3 miles or 25 minutes away.

Airports Distance
Airports Distance
Sarasota/Bradenton International
 Drive: 25 min 11.3 mi
Getting Around
Somewhat Walkable
Walkability
30 / 100
Minimal Public Transit
Transit
0 / 100
Exceptionally Drivable
Drivability
90 / 100
Moderately Bikeable
Bikeability
60 / 100

Scores provided by

What do Walkability, Transit, Drivability, and Bikeability mean? Walkability measures the walking distance to day-to-day needs. Transit measures access to public transportation. Drivability measures congestion, parking availability, and access to major roads. Bikeability measures the suitability for cycling. How It Works
Active
Soundscore™
79 / 100

Traffic

Busy

Airport

Calm

Businesses

Calm

Scores provided by

HowLoud What is a Sound Score Rating? A Sound Score Rating aggregates noise caused by vehicle traffic, airplane traffic and local sources. How It Works
Points of Interest

Time and distance from 5577 Contento Dr.

Shopping Centers Distance
Shopping Centers Distance
5263 Ocean Blvd
Drive: 5 min 1.5 mi
Siesta Beach Plaza
Drive: 5 min 1.6 mi
210-240 Avenida Madera
Drive: 6 min 1.7 mi
5577 Contento Dr has 3 shopping centers within 1.7 miles, which is about a 6-minute drive. The miles and minutes will be for the farthest away property.
Parks and Recreation Distance
Parks and Recreation Distance
Phillippi Estate Park
 Drive: 9 min 4.0 mi
Red Bug Slough Preserve
 Drive: 13 min 5.9 mi
Marie Selby Botanical Gardens
 Drive: 14 min 6.1 mi
Urfer Family Park
 Drive: 18 min 8.9 mi
Mote Marine Aquarium
 Drive: 24 min 10.4 mi
5577 Contento Dr has 5 parks within 10.4 miles, including Phillippi Estate Park, Red Bug Slough Preserve, and Marie Selby Botanical Gardens.
Hospitals Distance
Hospitals Distance
Sarasota Memorial Hospital
Drive: 11 min 5.4 mi
Doctors Hospital of Sarasota
Drive: 18 min 9.3 mi
5577 Contento Dr is 5.4 miles from Sarasota Memorial Hospital, and is convenient to other hospitals, including Doctors Hospital of Sarasota.
Military Bases Distance
Military Bases Distance
Governmental U.S. Coast Guard
Drive: 80 min 54.6 mi
MacDill Air Force Base
Drive: 96 min 63.2 mi
5577 Contento Dr is 54.6 miles from Governmental U.S. Coast Guard, and is convenient to other military bases, including MacDill Air Force Base.

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