Sales/Leases

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
$7,500 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 terdei@me.com or call 941-402-2142 for photos and questions.
August 1, 2024 thru November 1, 2024- $7,500 2 month minimum
Listing Image 1922 Harbourside Dr. #1104 Longboat Key, FL 34228
$8,500 per month
2 Bed | 2 Bath | 1,350 Sq Ft
2 Bed, 2 Bath, 1350 SqFt.
Minimum 3 month stay.
Available 01 September 2024 through 30 January 2025.
Bright and spacious, fully furnished, holiday townhouse/villa with pool and garden access.
Sorry, no pets.
Listing Image 1926 Harbourside Dr Longboat Key, FL 34228
$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.

$6000 April - November 2024
$9000 November 2024 - March 2025
Listing Image 1928 Harbourside Dr #1404 LONGBOAT KEY, FL 34228   (Updated)
$6,000 per month
2 Bed | 2 Bath | 2,565 Sq Ft | Unite Acres
NOW OFFERING SEASONAL RENTALS: THIS TOWNHOME IS A MUST SEE!
This home was over the top completely renovated by a custom home builder. With this renovation an additional 900+ sq/ft was added to the first level of this beautiful 2 bedroom, 2 bathroom home. Greeted with high ceilings, a cozy wood burning fireplace and a peek a boo view of the bay, you will be right at home! Some of the upgrades include a full custom kitchen with Cambria quartz counters and soft close cabinetry, wide naturally aged plank flooring throughout the upper floor, Italian porcelain tile in both baths, LED recessed lights, new garage doors, a new epoxy garage floor, and much much more!! Use the beautifully crafted Italian spiral staircase to access the lower level of the home where you will find a bonus living space with 2 beds, a living area, dining room and large laundry room. An oversized 2 car garage and storage area is a rare thing to be found on the keys! 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 & pickle ball. Within one mile to Publix & less than 10-minute drive to shopping & dining at St. Armand's Circle. Private beach amenities were also just renovated! Visit the web link to see more pics.

$6000 per month (April thru October 2024)
$8000 per month (November 2024 thru March 2025)
Listing Image 1932 HARBOURSIDE DR UNIT 216 LONGBOAT KEY, FL 34228
$5,500 per month
2 Bed | 2 Bath | 1 Sq Ft | Unite Acres
Two Bedroom / Two Bath. Available first week of April 2024. Minimum rental 60 days. No pets. Prefer long term rental.

$5,500 April to November 2024
$7,500 December to March 2025
Listing Image 1932 Harbourside Drive Unit 242 Longboat Key, FL 34228
$7,500 per month
2 Bed | 2 Bath | 1,342 Sq Ft
Sarasota Bay views are enjoyed from this two bedroom/ two bath residence behind the prestigious Bay Isles gates in the pet friendly community of Fairway Bay. Relax with your morning coffee on the 4th story terrace while you watch the tranquil water and wildlife over the mangroves and Bay. The resort-style amenities pamper owners and guests with tennis & pickle ball courts, swimming pools & spas, an updated state-of-the-art fitness center, walking trails, planned activities and a spacious clubhouse perfect for larger, casual gatherings. This residence also comes with one under building parking space and a membership to the exclusive Bay Isles Beach Club. Join the Longboat Key Club to take advantage of 45 holes of Championship Golf, Spa & Wellness Center, Longboat Key Club Moorings, eight on-site exclusive restaurants and lounges, The Tennis Gardens and more! Fairway Bay's convenient mid-key location is just minutes from the fine dining and shops of St. Armands Circle, Lido beach, and the cultural hub of downtown Sarasota.

Condo comes with Wi-fi, utilities, and cable included.

4 Month Minimum rental
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