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$4,995
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Property Description
Experience luxury island living in this beautifully remodeled 2-bedroom, 2-bath residence located in the highly sought-after Fairway Bay community within Bay Isles on Longboat Key. Available for immediate occupancy, this turnkey furnished coastal retreat offers flexible lease terms from 6 to 12 months. Step inside to discover a bright and open floor plan featuring upscale contemporary finishes, , updated flooring, a stunning modern kitchen with premium appliances, and elegantly renovated bathrooms. The spacious primary suite provides a peaceful retreat, while the second bedroom offers comfortable accommodations for guests or an ideal home office. Expansive living spaces and a private balcony create the perfect setting to relax and enjoy the Florida lifestyle. Residents of Fairway Bay enjoy an exceptional array of resort-style amenities, including a heated community pool, a beautifully maintained clubhouse, and a fully equipped fitness center. Tennis and pickleball enthusiasts will appreciate access to two regulation tennis courts that can also be configured into four pickleball courts, offering year-round recreation just steps from home. As part of the exclusive Bay Isles community, residents also enjoy access to the private Bay Isles Beach Club, featuring deeded Gulf-front beach access with some of Longboat Key's most beautiful sand beaches. The Beach Club offers gated parking, picnic areas, grills, restrooms, and the perfect setting to enjoy spectacular Gulf sunsets. Outdoor enthusiasts will also appreciate access to the Bay Isles marina area and kayak launch with direct access to Sarasota Bay. Ideally situated on Longboat Key, this residence is just minutes from St. Armands Circle, Longboat Key Club, championship golf courses, waterfront dining, marinas, boutique shopping, and the cultural attractions of downtown Sarasota. Whether you're seeking a seasonal retreat or an extended island stay, this residence offers the perfect combination of luxury, convenience, and coastal living. Available immediately with lease terms ranging from 6 to 12 months.
Full Property Details
Full Property Details for 2020 Harbourside Dr #446
General
- Rent: $4,995
- Status: Active
- Type: Condo
- Source: MidFloridaRegionalMLS
- MLS ID: A4695127
- Updated: 7/2/2026
- Added to Site: 46 day(s) ago
Rental Information
- Lease/Rent Term: 12 Months
- Min. Lease: 6 Months
Interior
- Number of Rooms: 1
- Interior Features: Ceiling Fan(s), Living Room/Dining Room Combo, Thermostat
- Appliances: Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Ice Maker, Microwave, Range, Refrigerator, Washer
- Furnishings: Unfurnished
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 2
Other Rooms
- Laundry: Inside
Exterior
- Exterior Features: Tennis Court(s)
- Deck/Patio: Covered, Patio
- Porch/Patio/Deck: Covered, Patio
Parking
- Garage: Yes
- Garage Spaces: 1
- Covered Spaces: 1
Location
- Area: 34228 - Longboat Key
- County: Sarasota
- Development Name: 34228 - Longboat Key
- Subdivision: FAIRWAY BAY 2 PH 1
- Driving Directions: From I-75, take University Parkway west toward Sarasota/Longboat Key. Continue onto Gulf of Mexico Drive through St. Armands Circle and follow Gulf of Mexico Drive north onto Longboat Key. Turn into the Bay Isles entrance and continue to Bay Harbour. The residence is located at 2020 Harbourside Drive, Unit 446.
Community
- Community Name: 34228 - Longboat Key
- Community Features: Clubhouse, Fitness Center, Gated Community - Guard, Tennis Court(s)
- Association: Yes
- Assoc. Name: JT
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Structural Information
- Stories/Levels: One
- Square Feet: 1,270
- Year Built: 1984
Lot Features
- Property View: Water
- Lot Size (Acres): 3.9
- Lot Size (Sq. Ft.): 169,941
- Lot Size: 3.9013
- Street/Road Desc.: Asphalt
Water Features
- Water Front: Yes
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Bay/Harbor, Gulf/Ocean, Gulf/Ocean to Bay
- Water Front Desc.: Bay/Harbor, Gulf/Ocean
Financial Considerations
- Lease Price: $4,995
- Assoc Fee Desc.: None
- Application Fee: $100
Disclosures and Reports
- APN: 8022053
- Property ID: 8022053
Listed by Vive Realty
Schools
Schools serving 2020 Harbourside Dr #446
School District:Sarasota County School District
| Name | Grades | Distance |
|---|---|---|
Southside Elementary School, Sarasota, FL 1901 Webber Street, Sarasota, FL 34239 | PK-5 | 6.1 mi |
Booker Middle School 2250 Myrtle Street, Sarasota, FL 34234 | 6-8 | 5.4 mi |
Booker High School 3201 North Orange Avenue, Sarasota, FL 34234 | 9-12 | 4.5 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price History for 2020 Harbourside Dr #446
Date
Details
Price
Change
Source
6/26/2026
Price Reduced
$4,995
-9.1%
MLS
6/13/2026
Price Reduced
$5,495
-7.65%
MLS
5/28/2026
Listed
$5,950
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
2020 Harbourside Drive #446, Longboat Key, FL 34228 (MLS# A4695127) is a Condo property with 2 bedrooms and 2 full bathrooms. 2020 Harbourside Drive #446 is currently listed for rent at $4,995 and was received on May 28, 2026. Want to learn more about 2020 Harbourside Drive #446? Do you have questions about finding other real estate for sale or rent in Longboat Key? You can browse all Longboat Key rentals or contact a Coldwell Banker agent to request more information.

