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 1904 Harbourside Dr Unit 204 Longboat Key, Fl 34228
$12,000 per month
3 Bed | 3 Bath | 2,258 Sq Ft
This grand townhouse is perfect for family and entertaining guests. It’s move in ready to enjoy a little piece of paradise in Fairway Bay, a much sought after location on Longboat Key.
There is a two month minimum. Price per month is flexible depending upon the months and length of stay.
Listing Image 1918 Harbourside Drive Unit 903 Longboat Key, FL 34228
$10,000 per month
2 Bed | 2.5 Bath | 1,662 Sq Ft | Unite Acres
Manatees, dolphins, pelicans... oh my. Designer renovated bayfront townhouse with private garage. Spectacular views of bay, Ringling Bridge and downtown Sarasota. King-size bed in master bedroom with 2 walk-in closets and a glass enclosed shower that looks out onto Sarasota Bay. Office doubles as a guest bedroom with a plush, extra thick Murphy bed and its own glass enclosed shower. Gourmet kitchen has everything you need to cook if you desire. Living room with large TV. There is a private boat dock as well if you want to bring your boat. New community exercise room, pool and social room for gatherings. Private beach club with gated access. What did I forget? Just ask me. There is more ... Rates can vary with month renting. 2 month rental minimum. April and May 2026 still available.
Listing Image 1932 Harbourside Drive #244 Longboat Key Florida, FL 34228
$8,970 per 6 months
2 Bed | 2 Bath
A completely renovated newly furnished 2 bedroom . 2 bath condo at Fairway Bay I of Bay Isle Community. This gorgeous condo is located behind 24 hour man security gates on South Longboat Key. (1) Parking space located under the building. Access keyed entry to the building. Condo is located on the 5th floor with southern views toward downtown Sarasota Bay. Coastal Contemporary completely new finishes. The condo was completely renovated from the top to bottom. All high end finishes to enjoy your stay.
A - 3 month stay required during the season and A - 2 month stay required for non-season. Non-seasonal rate is $5500 a month. Condo Association application required and $150.00 fee.
The amenities included a keyed access to the fitness center. Two swimming pools and hot tubs for Fairway Bay residence. All Bay Isle residence include keyed access to The Bay Isle Private Beach Club located on Gulf of Mexico Drive, approximately a 4 minute drive or walk. The club has newly renovated restroom and covered outdoor picnic tables. A clear kayak is located in our parking spot for your use at your own risk. Tennis courts are available. The condo provides a great location on Longboat Key island. Walking distance to Publix, Marina and driving distance to St. Armand's Circle and downtown Sarasota. The views from the balcony provide sunrises in the morning and downtown Sarasota and the Ringling Bridge lighted up at night. Sunsets can be viewed from The Bay Isle Private Club.
The condo provides a California King size memory foam bed for the master suite. Plenty of in built cabinets for storage. Two closet for hanging clothes. The master bath provides a Toto water closet with operational controls and walk in shower. A lockable built in safe in the master closet. Wall mounted built in ironing board and iron. The guest suite provides a queen memory foam bed. Built in wardrobe and drawers. The bathroom provides a Victoria Albert Volcanic Limestone Tub and rain shower head and Toto automatic water closet. All windows and doors are hurricane glass with automatic blinds. Whirlpool full size washer and dryer. A tank-less water heater. Pompeii Pure White Quartz -waterfall edge at the kitchen island. Bertazzoni Stove - Cooktop - Refrigerator - Dishwasher. Mielle Built in coffee espresso maker. A cusinart coffee maker also provided on the counter. Iotty Smart Light switches. Nest Thermostat.

Listing Image 2012 HARBOURSIDE DR, Unit 2101 Longboat Key, FL 34228
$14,000 per month
3 Bed | 3 Bath | 2,135 Sq Ft
This bright and airy Fairway Bay townhouse, situated on the Sarasota Bayfront, offers a luxurious winter retreat. The fully furnished, turnkey condo boasts three bedrooms (two ensuite), three bathrooms, a den, a two-story living room with fireplace, an open kitchen featuring a large island, a screened lanai, and two balconies providing stunning views of Sarasota Bay and the downtown area. Additional features include a dedicated laundry room and a two-car garage.