Single Family Residence
$18,500/mo
3
Beds
3
Baths
2,647
Sqft
Experience resort-style living in this beautifully updated custom home, now available for seasonal or annual rental in the prestigious Windstar on Naples Bay community. Offering a rare combination of luxury, comfort, and lifestyle amenities, this residence is perfect for those seeking an elevated Naples experience. Inside, the home showcases refined craftsmanship with custom 8-foot solid-core doors, premium hardware, plantation shutters, and a striking marble-faced fireplace. The spacious chef’s kitchen is designed for both everyday living and entertaining, featuring custom cabinetry, a large walk-in pantry, and updated appliances. Skylights and custom lighting enhance the bright, inviting atmosphere, while a dedicated home office provides a quiet space for work or relaxation. Seamless indoor-outdoor living is at the heart of this property. Expansive 10-foot sliding glass doors open to a private tropical courtyard complete with a heated pool, spa, and tranquil waterfall. A separate guest cabana offers ideal accommodations for visitors, creating a true retreat-like setting. From the screened lanai, enjoy serene views of the golf course, lake, and surrounding mangroves—perfect for morning coffee or evening sunsets. Additional conveniences include storm shutters, a central vacuum system, brick paver driveway, a two-car garage, and an AquaLink system for effortless pool and spa control. As a resident, you’ll have access to the exceptional amenities of Windstar, including a Tom Fazio-designed championship golf course, a newly renovated clubhouse overlooking Naples Bay, a deep-water marina with direct Gulf access in minutes, clay tennis courts, and a state-of-the-art fitness center. The private Keewaydin Island Beach Club, accessible via shuttle boat, offers a truly unique coastal experience. A transferable golf membership may be available, allowing tenants to fully enjoy the exclusive lifestyle this community is known for. This is a rare opportunity to lease a luxury home in one of Naples’ most sought-after gated waterfront and golf communities.
132 days on market · Listing updated April 24, 2026
| Date | Event | Price |
|---|---|---|
| Apr 24, 2026 | Original list price | $18,500 |
Reflects listing data on file, not a complete transaction history.
Listed by Kimberly Alvord, John R Wood Properties
Co-listed by Tyler Bradley, John R Wood Properties
$18,500/mo
3296 LOOKOUT LN, NAPLES
The data relating to real estate for sale displayed on this Website comes in part from the Multiple Listing Service of the Bonita Springs-Estero Association of REALTORS®, Inc., under License No. BK3468074. Properties displayed on this Website include properties listed with brokerage firms other than Sands Real Estate & Property Management. Detailed information about such properties includes the name of the brokerage firm with which the seller has listed the property. The properties displayed may not be all the properties listed with brokerage firms participating in the Bonita Springs-Estero Association of REALTORS® Multiple Listing Service, or contained in the database compilation of the Bonita Springs-Estero Association of REALTORS® Multiple Listing Service.