3296 Lookout Ln, Naples, FL 34112
For Rent Season Rate: $18,500 Off-Season Rate: $18,500 Rate: $18,500
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Listing Agent: Kimberly Alvord
Agent Phone:
239-919-2742
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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.
Bar
Built- In Cabinets
Cathedral Ceiling(s)
Foyer
Laundry Tub
Pantry
Pull Down Stairs
Smoke Detectors
Walk- In Closet(s)
Window Coverings
Beach - Private
Beach Club Included
Cabana
Fitness Center
Golf Course
Internet Access
Private Membership
Putting Green
Restaurant
Sidewalk
Streetlight
Tennis Court(s)
Underground Utility
Screened Lanai/ Porch
Courtyard
Electric Cooktop
Dishwasher
Disposal
Dryer
Microwave
Refrigerator/ Freezer
Wall Oven
Washer
Wine Cooler
Y
Building Description: Ranch, Single Family
Community Type: Gated
MLS Area: Windstar
Total Square Footage: 3,196
Total Floors: 1
Date Listed: 2026-04-24 00:00:00
Pool: Y
Pool Description: Pool/ Spa Combo, Below Ground, Concrete, Equipment Stays, Electric Heat, Screen Enclosure
Private Spa: Y
Furnished: Turnkey
Windows: Window Coverings
Parking: Attached
Garage Description: Y
Garage Spaces: 2
Attached Garage: Y
Flooring: Tile, Vinyl, Wood
Heating: Central Electric
Cooling: Ceiling Fan(S), Central Electric
Security: Smoke Detector(S), Gated Community
Laundry: Laundry In Residence, Laundry Tub
Pets: With Approval
Restrictions: No Commercial, No R V
Rear Exposure: W
Amenities: Beach - Private, Beach Club Included, Cabana, Fitness Center, Golf Course, Internet Access, Private Membership, Putting Green, Restaurant, Sidewalk, Streetlight, Tennis Court(S), Underground Utility
Listing Courtesy Of: John R Wood Properties
2394340101
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.
Property Details
Price: $18,500
Sq Ft: 2,647
($7 per
sqft)
Season Rate: $18,500
Off-Season Rate: $18,500
Bedrooms: 3
Bathrooms: 3
City: Naples
County: Collier
Type: Single Family
Development: Windstar
Subdivision: Spyglass Pointe
Acres: 0.2500
Year Built: 1999
Listing Number: 226017051
Status Code: A-Active
Garage:
2
/
Y
Furnishings: Turnkey
Pets Allowed: With Approval
Interior Features:
Bar
Built- In Cabinets
Cathedral Ceiling(s)
Foyer
Laundry Tub
Pantry
Pull Down Stairs
Smoke Detectors
Walk- In Closet(s)
Window Coverings
Amenities:
Beach - Private
Beach Club Included
Cabana
Fitness Center
Golf Course
Internet Access
Private Membership
Putting Green
Restaurant
Sidewalk
Streetlight
Tennis Court(s)
Underground Utility
Exterior Features:
Screened Lanai/ Porch
Courtyard
Equipment:
Electric Cooktop
Dishwasher
Disposal
Dryer
Microwave
Refrigerator/ Freezer
Wall Oven
Washer
Wine Cooler
View:
Y
Additional Information:
Building Description: Ranch, Single Family
Community Type: Gated
MLS Area: Windstar
Total Square Footage: 3,196
Total Floors: 1
Date Listed: 2026-04-24 00:00:00
Pool: Y
Pool Description: Pool/ Spa Combo, Below Ground, Concrete, Equipment Stays, Electric Heat, Screen Enclosure
Private Spa: Y
Furnished: Turnkey
Windows: Window Coverings
Parking: Attached
Garage Description: Y
Garage Spaces: 2
Attached Garage: Y
Flooring: Tile, Vinyl, Wood
Heating: Central Electric
Cooling: Ceiling Fan(S), Central Electric
Security: Smoke Detector(S), Gated Community
Laundry: Laundry In Residence, Laundry Tub
Pets: With Approval
Restrictions: No Commercial, No R V
Rear Exposure: W
Amenities: Beach - Private, Beach Club Included, Cabana, Fitness Center, Golf Course, Internet Access, Private Membership, Putting Green, Restaurant, Sidewalk, Streetlight, Tennis Court(S), Underground Utility
Map of 3296 Lookout Ln, Naples, FL 34112
Listing Courtesy Of: John R Wood Properties
2394340101