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.

	1918 Harbourside Drive Unit 903 Longboat Key, FL 34228 $12,000 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. Now booking for fall/winter 2026/2027. + 150 HOA application fee + $1000 refundable deposit.

	1930 Harbourside Dr Longboat Key, FL 34228 $7,000 per month Furnished 2 Bedroom, 2 Bath Condo Overlooking Sarasota Bay, Bay Isles, Longboat Key $150 application fee \| $1,000 security deposit Two-month minimum stay required for January, February, and March. Contact the owner directly: Johnny, (925) 822-8087 This furnished 2-bedroom, 2-bath, 1,192 sq ft condominium is on the 2nd floor of Fairway Bay I, a five-story midrise with seven units per floor, overlooking beautiful Sarasota Bay. Fairway Bay I is in the exclusive gated community of Bay Isles, with 24/7 guarded access and a scenic walking path along the bay. Enjoy sunrises over the water from the private balcony, and watch the sunset over the Gulf of Mexico from the Bay Isles Beach Club. Keyed access to the fitness center and clubhouse. Two heated swimming pools and hot tubs. Tennis and pickleball courts. Keyed access to the private Bay Isles Beach Club on the Gulf of Mexico, a 5-minute drive or short walk across Gulf of Mexico Drive. The beach club has newly renovated restrooms, covered picnic tables, charcoal grills, a refrigerator, and an ice machine. Located on south Longboat Key, within walking distance of Publix, CVS, and the Longboat Key Club Marina. A short drive to St. Armands Circle, downtown Sarasota, and a variety of great restaurants on Longboat Key.

	1930 HARBOURSIDE DR, #122, Longboat Key, FL 34228 $499,000 2 Bed \| 2 Bath \| 1,192 Sq Ft \| Unite Acres Welcome to your waterfront retreat in the highly sought-after Fairway Bay community, where relaxed coastal living meets thoughtful design and modern comfort. This beautifully renovated 2-bedroom, 2-bath condominium offers nearly 1,200 square feet of light-filled interior space, along with sweeping views of Sarasota Bay and the downtown skyline that create a stunning and ever-changing backdrop throughout the day. Fully updated in 2020 and professionally curated by an interior designer, the residence showcases a refined yet inviting aesthetic. Inside, the open-concept layout is enhanced by warm, driftwood-inspired luxury vinyl plank flooring and an abundance of natural light. The living and dining areas flow effortlessly together, while expansive pocketing sliders open wide to a private balcony, creating a seamless indoor-outdoor experience ideal for both quiet mornings and evening entertaining. From this vantage point, you can take in tranquil water views, coastal breezes, and vibrant sunsets that define the Longboat Key lifestyle. The galley-style kitchen is both stylish and functional, featuring quartz countertops, crisp Ivory soft-close cabinetry, New AC 2025, New Water Heater 2025, New Washer and Dryer 2025, stainless steel appliances installed in 2020, and a peninsula with seating that invites casual dining and conversation. The design balances clean lines with timeless finishes, making it equally suited for everyday living and hosting guests. The spacious primary suite serves as a private sanctuary, offering generous proportions, beautiful bay views, and direct access to the peaceful ambiance of the home. The en-suite bath is thoughtfully appointed with dual vanities, elegant lighting, and a walk-in tiled shower, creating a spa-like atmosphere. The guest bedroom and accompanying bath are equally well-designed, providing comfort and privacy for visitors while maintaining the home’s cohesive style. Additional features include plantation shutters on all windows and sliders, a private exterior entrance that enhances both convenience and privacy, a welcoming balcony seating area, and professionally landscaped surroundings that add to the property’s curb appeal. Important updates such as a new air conditioning system and water heater provide peace of mind, making this a truly move-in-ready opportunity.

	1932 Harbourside Dr, Unit 242 Longboat Key, FL 34228 $649,000 2 Bed \| 2 Bath \| 1,192 Sq Ft Secured entry, 24/7 guarded access, spectacular water views, a clubhouse, fitness center, heated pool and spa, BBQ area, tennis and pickleball courts, and scenic walking trails. The community also offers deeded access to Bay Isles private Beach Club, allowing you to fully embrace Longboat Key’s coastal lifestyle. This stunning 2-bedroom, 2-bath condominium in the exclusive community of Bay Isles. This 4th floor residence in a mid-rise five-story building combines comfort, style, and peace of mind with secure entry and 24/7 guarded access. Instantly captivating with a light-filled, open atmosphere thoughtfully crafted to highlight the stunning waterfront bay views. The spacious kitchen, positioned at the front of the residence, provides ample room for meal preparation while still enjoying the scenery. It flows seamlessly into the dining and living areas, where a large sliding glass door opens to a private balcony creating an unforgettable indoor-outdoor living experience with spectacular water views.

	2002 Harbourside Drive Longboat key , FL 34228 $8,900 per month 2 Bed \| 2 Bath Townhouse available December 2026-May 2027 ( or longer ) . Minimum stay 3 months. Monthly rent + one time $150 application fee, $1000 refundable deposit and $250 one time cleaning fee.