3296 Lookout Ln

$18,500
Price
2,647 Sq. Ft.
$84 / Sq. Ft.
2,647
Sq. Ft.
$84
per Sq. Ft.

Description

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...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.
  1. Listed by Kimberly Alvord • John R Wood Properties
  2. Listed by Tyler Bradley • John R Wood Properties

Property Details for 3296 Lookout Lane

Area
NA08 - Royal Harbor-Windstar Are
Development
WINDSTAR
Sub Condo Name
SPYGLASS POINTE
Waterfront
No
Waterfront Desc
None
View
Lake, Landscaped Area, Mangroves, Water
Furnished Desc
Turnkey
LISTING UPDATED: 04/24/2026 07:35 PM

Property Details for 3296 Lookout Lane

StatusActive
MLS #226017051
Days on Market10
Rental Incentives-
Costs & Fees-
Available Date04/24/2026
Lease TermLease Length: 30
Furnished-
Property TypeRental
MLS TypeResidential Rental / Single Family
Year Built1999
Lot Size0.25 AC / 10,890 SF
CountyCollier County

Location

Listing Courtesy of John R Wood Properties, Kimberly Alvord; John R Wood Properties, Tyler Bradley
Add your commute

Building Information for 3296 Lookout Lane

Building/Complex3296 Lookout LnFloor-Stories1Pet Policy-Pet Policy DetailsWith ApprovalYear Built1999Building Size-Lot Size0.25 AC / 10,890 SF

Property Information for 3296 Lookout Lane

Summary
Location and General Information
  • 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
  • Community Type: Fitness Center, Golf Course, Putting Green, Restaurant, Sidewalks, Street Lights, Tennis, Gated
  • Pets: With Approval
  • Property Features: Cable Prewire
Parking
  • Carport Desc: Attached
  • Carport Spaces: 0
  • Attached Garage: Yes
  • Garage Spaces: 2
  • Carport: No
  • Covered Spaces: 2
  • Garage: Yes
  • Total Parking: 0
Interior and Exterior Features
Interior Features
  • Laundry Features: Laundry in Residence, Laundry Tub
  • Approx Living Area: 2647.0
  • Living Area Units: Square Feet
  • Bedrooms: 3 Bed
  • Elevator: None
  • Appliances: Electric Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator/Freezer, Wall Oven, Washer, Wine Cooler
  • Equipment: Auto Garage Door, Cooktop - Electric, Dishwasher, Disposal, Dryer, Microwave, Refrigerator/Freezer, Smoke Detector, Wall Oven, Washer, Wine Cooler
  • Flooring: Tile, Vinyl, Wood
  • Interior Features: Bar, Built-In Cabinets, Cathedral Ceiling, Foyer, Laundry Tub, Pantry, Pull Down Stairs, Smoke Detectors, Walk-In Closet, Window Coverings, Cable Prewire
  • Spa Features: Below Ground, Concrete, Equipment Stays, Heated Electric, Pool Integrated, Screened
  • Private Pool Desc: Pool/Spa Combo, Below Ground, Concrete, Equipment Stays, Electric Heat, Screen Enclosure
  • Private Pool: Yes
  • Private Spa: Yes
  • Total Floors: 1
  • Baths Full: 3
  • Half Bathrooms: 0
  • Bathrooms Total Decimal: 3.00
  • Bathrooms: 3
  • Bedrooms Total: 3
  • Fireplace: No
  • View YN: Yes
  • Additional Rooms: Great Room, Guest Bath, Guest Room, Laundry in Residence, Screened Lanai/Porch
Exterior Features
  • Exterior Features: Screened Lanai/Porch, Courtyard, Cabana, Tennis Court(s)
  • Windows: Window Coverings
Property Information
Utilities
  • Cooling: Ceiling Fan(s), Central Electric
  • Cooling YN: Yes
  • Heat: Central Electric
  • Heating YN: Yes
Lot Information
  • Structure Type: House
Rental
Rental Information
  • Availability Type: Monthly
  • Off Season Rate: $18,500.00
  • Season Rate: $18,500.00
  • Horse: No
  • Smoking YN: No
  • Min Days of Lease: 30

Property History for 3296 Lookout Lane

DateEvent & SourcePriceAppreciation
Apr 24, 2026

Listed (Active)

Naples Area Board of REALTORS #226017051

$18,500
DateEvent & SourcePrice
04/24/2026

Listed (Active)

Naples Area Board of REALTORS #226017051

$18,500

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Schools near 3296 Lookout Lane

This home is within Collier.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - 6 to 8
Public - 9 to 12
Public - 9 to 12
Rating
School
Distance
Avalon Elementary School
PublicPK to 5

Gulfview Middle School
Public6 to 8

Naples High School
Public9 to 12

Beacon High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

3296 Lookout Lane is available for rent in Naples, FL 34112. This property was listed on April 24, 2026 by John R Wood Properties, it's currently listed at $18,500. This listing's school district is Collier. Nearby schools include Avalon Elementary School, Gulfview Middle School and Naples High School. 3296 Lookout Lane is a 3-bed, 3-bath, 2,647 sqft a property built in 1999.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the owner. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of John R Wood Properties, Kimberly Alvord; John R Wood Properties, Tyler Bradley

The information is being provided in part by Southwest Florida Multiple Listing Service, Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2, and MarcoMls. Information deemed reliable but not guaranteed. Information is provided for consumers' personal, non-commercial use, and may not be used for any purpose other than the identification of potential properties for purchase. Copyright 2026 Southwest Florida Multiple Listing Service and MarcoMls. All Rights Reserved. The data relating to real estate for sale displayed on this website comes in part from the Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2 and MarcoMls. Properties listed with brokerage firms other than Compass are marked with the "BR House" logo. 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 Naples MLS BR Program, or contained in the database compilation of Naples MLS.