
3296 Lookout Ln, Naples, FL 34112
What This House Offers
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.
Unit
- $18,500 / month
- 3 Beds
- 3 Baths
- 2647 sq. ft.
- Available Now
Home Features
- Attic
- Dishwasher
- Disposal
- Freezer
- High Speed Internet Access
- Microwave
- Oven
- Pantry
- Range
- Refrigerator
- Sprinkler System
- Walk-In Closets
Community Features
- Courtyard
- Fitness Center
- Putting Greens
- Spa
- Tennis Court
3296 Lookout Ln is a single-family home for rent in Naples, FL
Fees and Policies
The fees below are based on community-supplied data and may exclude additional fees and utilities.
One-Time Move-In Fees
- Security Deposit Refundable - Refundable$18500
No Pets Allowed
Property Fee Disclaimer Based on community-supplied data and independent market research. Subject to change without notice. May exclude fees for mandatory or optional services and usage-based utilities.
Home Details
Views
- Lake
- Mangrove
Home Design
- Built in 1999
- Turnkey
- Single Family Detached Home
Interior Spaces
- Cathedral Ceiling
- Great Room
- Screened Porch
- Fireplace
- Plantation Shutters
- Bar
- Entrance Foyer
- Ceiling Fan
- Property has 1 Level
Kitchen
- Built-In Oven
- Wine Cooler
- Electric Cooktop
- Freezer
- Microwave
- Dishwasher
- Built-In or Custom Kitchen Cabinets
- Disposal
Flooring
- Wood
- Tile
- Vinyl
Bedrooms and Bathrooms
- In-Law or Guest Suite
- Walk-In Closet
- 3 Full Bathrooms
- 3 Bedrooms | 3 Bathrooms
- 3 Bedrooms
Laundry
- Dryer
- Laundry in unit
- Laundry Tub
- Washer
Attic
- Pull Down Stairs to Attic
Home Security
- Fire and Smoke Detector
Parking
- 2 Car Attached Garage
Pool
- Cabana
- Heated Pool and Spa
- Concrete Pool
- Heated In Ground Pool
- Heated Spa
- In Ground Spa
- Screened Spa
- Screen Enclosure
- Pool Equipment Stays
Outdoor Features
- Tennis Courts
- Courtyard
Lot Details
- Private Beach
- 10890 Sq Ft Lot
- Landscaped
Utilities
- Central Heating and Cooling System
- Cable TV Available
- Underground Utilities
- Internet Available
Listing and Financial Details
- Assessor Parcel Number 82860000268
- No Smoking Allowed
Community Details
Overview
- Private Membership Available
- Spyglass Pointe Subdivision
Amenities
- Restaurant
Recreation
- Golf Course Community
- Community Cabanas
- Fitness Center
- Tennis Courts
- Putting Green
Pet Policy
- Pets allowed on a case-by-case basis
Security
- Gated Community
Explore Commute Options
- Drive Time--
- Walk Time--
- Bike Ride Time--
- Public Transit--
Get In Touch
Naples, FL 34112

Information is provided by The Florida Gulf Coast Multiple Listing Service, Inc. Information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Listing(s) information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Copyright © 2026 The Florida Gulf Coast Multiple Listing Service, Inc. All rights reserved.
Area Scores
Walkability
Somewhat walkable20 / 100
Driveability
Exceptionally drivable90 / 100
Bikeability
Moderately bikeable60 / 100
Travel and Transit

Local Education
Primary and Secondary Schools
Beacon High School
Grades 9-12
Public
International Learning Academy
Grades 9-12
Private
Data provided by GreatSchools.org © 2026. All rights reserved.
Colleges and Universities
School
Commute Time (Distance)
Hodges University, Naples
Drive: 27 min (14.8 mi)
Discover East Naples, Naples, FL
Shopping Centers
Shoppers will appreciate 3296 Lookout Ln proximity to Pineland Plaza, Gulf Gate Plaza, and Gulf Gate South. Pineland Plaza is 1.7 miles away, and Gulf Gate Plaza is within a 21 minute walk.
Parks and Recreation
Recreational activities near 3296 Lookout Ln are plentiful. Discover 4 parks within 4.6 miles, including Naples Botanical Garden, Charlie C. Anthony Park, and Naples Zoo.
Airports
Living in East Naples provides easy access to Southwest Florida International, located just 52 minutes from 3296 Lookout Ln.
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