The Fairway Bay Association is not a rental agent.  Units for sale or rent are available directly from the owner of the unit and must be rented for a minimum of 2 months. 
For individual listings, please see the bottom of this page. You MUST then select a category of Sale or Lease.

Listing Image 1914 Harbourside Drive #701 Longboat Key , FL 34228   (Updated)
$15,000 per month
3 Bed | 4 Bath
3 bedrooms plus den, 4 bathrooms. Sleeps up to 12. Recently furnished; plus fresh paint and new flooring upstairs and in bedrooms. 3 lanai's with 2 overlooking beautiful water views. Excellent location and steps to kayak/paddle board launch with 2 kayaks and 2 paddle boards included in oversized 2 car garage. Private beach access to Bay Isles Beach Club with showers, grills, volleyball, and picnic tables. Workout facility, pickleball, tennis courts, pool and hot tub just steps away on premise. 4 TVs, cable, wifi and utilities included. Send email to or call 941-402-2142 for photos and questions.
August 2024 thru November 2024-2 month minimum at 11,000 per month
December 2024-May 2025-3 month minimum at 15,000 per month
Listing Image 1926 Harbourside Dr Longboat Key, FL 34228   (Updated)
$8,500 per month
2 Bed | 2.5 Bath | 1,690 Sq Ft | Unite Acres
GATED, DEEDED PRIVATE BEACH ACCESS! This is a rare thing to be found on the keys! The main level with plantation shutters and hardwood floors includes the kitchen, dining and living areas. The kitchen has Subzero and Jenn-Air built in stainless steel appliances and granite countertops. A large second story skylight shines natural light through open ceilings onto the main floor dining area. The living area includes a fireplace and provides access to the back screened in lanai. Split bedrooms can be found on the 3rd level of the home. Both bedrooms have ensuite bathrooms and walk in closets. The owners ensuite bathroom includes dual sinks and a shower skylight. A heated pool is only steps away. Take advantage of the gym in the main clubhouse as well as the many amenities offered, including tennis. Membership to the Longboat Key Club is available for the ultimate Longboat Key lifestyle.
Listing Image 1930 Harbourside Dr Longboat Key, FL 34228
$9,000 per month
2 Bed | 2 Bath | Unite Acres

Listing Image 2016 Harbourside Drive Longboat Key, FL 34228   (New)
3 Bed | 3 Bath | 2,400 Sq Ft
Rarely available, unique double unit facing Downtown Sarasota is move in ready.

This unit offers two master suite bedrooms, large kitchen with breakfast area, walk-in laundry room, and more. Also included with this unit is a highly sought covered garage space.

Amenities include a beautiful clubhouse overlooking the pool, state of the art Fitness Center, Tennis/Pickleball, beautiful grounds, and located behind the gates of Bay Isles.

The sunrises are amazing from this 3rd floor unit.

Listing Image 2020 Harbourside Dr #431 Longboat Key, FL 34228
$6,000 per month
2 Bed | 2 Bath | 1,442 Sq Ft
Coveted corner unit. 2 balconies and office. Beautiful views of bay and sunset. Secure underground dedicated parking spot tastefully furnished and fully equipped. Unit is avail Sept2023 - end Jan 2024. Rent negotiable depending on length of lease. Call with questions. 202-222-5328