Listing Provided Courtesy of John R Wood Properties
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.
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
MLS #:
226017051
Status:
Active
Beds:
3
Baths:
3
Type:
Rental
Subtype:
Single Family Residence
Subdivision:
SPYGLASS POINTE
Neighborhood:
windstar
Listed Date:
Apr 24, 2026
Finished Sq Ft:
2,647
Total Sq Ft:
3,196
Lot Size:
10,890 sqft / 0.25 acres (approx)
Year Built:
1999
See this Listing
Schools
Interior
Appliances
Electric Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator/Freezer, Wall Oven, Washer, Wine Cooler
Bathrooms
3 Full Bathrooms
Cooling
Ceiling Fan(s), Central Electric
Flooring
Tile, Vinyl, Wood
Heating
Central Electric
Interior Features
Bar, Built-In Cabinets, Cathedral Ceiling(s), Foyer, Laundry Tub, Pantry, Pull Down Stairs, Smoke Detectors, Walk-In Closet(s), Window Coverings
Laundry Features
Laundry in Residence, Laundry Tub
Levels
1
Exterior
Architectural Style
Ranch, Single Family
Association 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
Attached Garage YN
1
Building Features
DSL/Cable Available
Community Features
Fitness Center, Golf, Putting Green, Restaurant, Sidewalks, Street Lights, Tennis Court(s), Gated
Covered Spaces
2
Exterior Features
Screened Lanai/Porch, Courtyard
Garage Spaces
2
Other Structures
Cabana, Tennis Court(s)
Parking Features
Attached
Security Features
Smoke Detector(s), Gated Community
Spa Features
Below Ground, Concrete, Equipment Stays, Heated Electric, Pool Integrated, Screened
View
Lake, Landscaped Area, Mangroves, Water
Waterfront Features
None
Window Features
Window Coverings
Financial
Map
Community
- Address3296 LOOKOUT LN NAPLES FL
- SubdivisionSPYGLASS POINTE
- CityNAPLES
- CountyCollier
- Zip Code34112
Subdivisions in NAPLES
- 291675 – ESPLANADE BY THE ISL PH2
- ACREAGE HEADER
- ARBORETUM A CONDO
- AVERSANA AT HAMMOCK BAY
- BAYVIEW ESTATES
- BRITTANY, THE A CONDO
- FAIRWAYS AT PRCL FOUR-ONE
- FOREST PARK
- FURSE LAKES CLUB
- GLADES COUNTRY CLUB APTS 2,THE
- GOLDEN GATE CITY
- GOLDEN GATE EST UNIT 76
- GOLDEN GATE ESTATE UNIT 1
- GOLDEN GATE ESTATE UNIT 10
- GOLDEN GATE ESTATE UNIT 23
- GOLDEN GATE ESTATE UNIT 26
- GOLDEN GATE ESTATE UNIT 37
- GOLDEN GATE ESTATE UNIT 39
- GOLDEN GATE ESTATE UNIT 40
- GOLDEN GATE ESTATE UNIT 43
- GOLDEN GATE ESTATE UNIT 46
- GOLDEN GATE ESTATE UNIT 59
- GOLDEN GATE ESTATE UNIT 64
- GOLDEN GATE ESTATE UNIT 67
- GOLDEN GATE ESTATE UNIT 70
- GOLDEN GATE ESTATE UNIT 76
- GOLDEN GATE ESTATE UNIT 78
- GOLDEN GATE ESTATE UNIT 79
- GOLDEN GATE ESTATE UNIT 83
- GOLDEN GATE ESTATE UNIT 84
- GOLDEN GATE ESTATE UNIT 86
- GOLDEN GATE ESTATE UNIT 87
- GOLDEN GATE ESTATE UNIT 88
- GOLDEN GATE ESTATE UNIT 89
- GOLDEN GATE ESTATE UNIT 9
- GOLDEN GATE ESTATE UNIT 91
- GOLDEN GATE ESTATE UNIT 92
- GOLDEN GATE ESTATE UNIT 96
- GOLDEN GATE ESTATES
- GOLF COTTAGES WYNDEMERE PH 1&2
- GOODLAND ISLES
- GULF HARBOR
- HUNTINGTON LAKES SIX
- ISLES OF CAPRI UNIT 2
- ISLES/COLLIER PRESERVE PH 17
- KEY ROYAL CONDO
- LAKE PARK
- MARIPOSA AT WHIPPOORWILL
- MILLBROOK FIDDLERS CREEK REPL
- N G & T C L F UNIT 2
- NAPLES MIMOSA CLUB
- NAPLES SANDPIPER BAY CLUB
- NAPLES WINTERPARK NORTH
- ORANGE BLOSSOM RANCH PH 1A
- PALM RIVER ESTATE UNIT 1
- PALM RIVER ESTATE UNIT 5
- PINE RIDGE
- PRESERVE AT THE SHORES
- REGENCY RESERVE A CONDO
- REGENCY WOODS CONDO
- REGENT PARK REP
- ROYAL PALM GOLF ESTATE UNIT 1
- SATURNIA LAKES 1
- STRATFORD PLACE
- TRAIL ACRES
- VALENCIA GOLF & CC PH 2
- VENTURA PH 2
- VILLAGE WALK PH 4
- WILDERNESS COUNTRY CLUB VII
- WILSHIRE LAKES PH 2
- WINDSTAR CONDO SEC
Market Summary
Property Summary
- Located in the SPYGLASS POINTE subdivision, 3296 LOOKOUT LN NAPLES FL is a Rental for sale in NAPLES, FL, 34112. It is listed for $18,500 To schedule a showing of MLS#226017051 at 3296 LOOKOUT LN in NAPLES, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
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