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MLS# 226017051 Property Photo

For Rent Season Rate: $18,500 Off-Season Rate: $18,500 Rate: $18,500 MLS# 226017051

Windstar, Spyglass Pointe

3296 Lookout Ln
Naples, FL 34112
Property Address

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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 res...

2647 Sqft, 0.25 Acres
3 Bed, 3 Bath
Status A-Active
Listing Courtesy of:
John R Wood Properties
Call: Kimberly Alvord 239-919-2742

MLS# 226026188 Property Photo

For Rent Season Rate: $8,500 Off-Season Rate: $3,500 Rate: $8,500 MLS# 226026188

Somerset At Windstar

2124 Paget Cir 1
Naples, FL 34112
Property Address

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Welcome to your perfect Naples getaway in the exclusive Somerset community at Windstar on Naples Bay! Residents can enjoy the Windstar Social Membership which grants access to four exquisite dining venues, premier tennis and bocce courts, a state-of-...

1908 Sqft, 0.07 Acres
3 Bed, 2 Bath
Status A-Active
Listing Courtesy of:
John R Wood Properties
Call: Stacey Cotter 239-349-2494

MLS# 226012976 Property Photo

For Rent Season Rate: $6,500 Off-Season Rate: $2,500 Rate: $6,500 MLS# 226012976

Windstar, Compass Point South

3538 Haldeman Creek Dr 113
Naples, FL 34112
Property Address

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Wake up to sweeping golf course views and end your day with a sunset boat ride to your own private island. This Naples gem is the lifestyle you’ve been dreaming of. This beautifully appointed two bedroom, two bath condo is set within an exclusive...

1414 Sqft,
2 Bed, 2 Bath
Status A-Active
Listing Courtesy of:
Diversified Real Estate Group
Call: Marie Vaughan 239-370-2575

By Owner Rentals

Listing# 96 Property Photo

FRBO Seasonal Rental $7,000

Windstar On Naples Bay,

3560 Windjammer Circle #1101
Naples, FL 34112
Property Address

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Enjoy your morning coffee with this fantastic view. An updated first-floor condominium is available for rent in the Spinnaker Pointe community of Windstar On Naples Bay. The fully furnished unit features a primary bedroom with a walk-in cl...

Listing# 50 Property Photo

FRBO Seasonal Rental $10,000 Membership Type(s): Transferable Soci [+ more]

Windstar On Naples Bay,

3705 Haldeman Creek Drive
Naples, FL 34112
Property Address

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MORNINGSTAR - GROUND FLOOR ON THE LAKE - SOCIAL MEMBERSHIP AVAILABLE Main floor 2000 Sq.Ft. Lives like a bungalow on the water, with your own PRIVATE OPEN AIR PATIO/GARDEN. SOCIAL MEMBERSHIP TO WINDSTAR CLUB AVAILABLE FOR...

2000 Sqft,
3 Bed, 2 Bath

Listing# 104 Property Photo

FRBO Seasonal Rental $7,500 Membership Type(s): Golf

Windstar On Naples Bay,

3576 Windjammer Circle
Naples, FL 34112
Property Address

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AVAILABLE for 2026-2027 Season with GOLF or Social available thru JAN 2027 - Two Master King Bedrooms (plus Den with Queen pullout Sofa for 3rd BR) - (POSSIBLE TRANSFERABLE GOLF & SOCIAL MEMBERSHIP UNTIL FEB 2027---Fees ...

2000 Sqft,
3 Bed, 2 Bath

Listing# 115 Property Photo

FRBO Seasonal Rental $9,000

Windstar On Naples Bay,

5060 Yacht Harbor Circle 203
Naples, FL 34112
Property Address

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NEWLY AVAILABLE EXCEPTIONAL WINDSTAR CONDO. Completely updated. Available Jan and/or February 2026. Relax & Unwind at Our Spacious Coastal Condo Enjoy comfort and convenience in this beautifully appointed condo featuring 3 spacio...

1822 Sqft,
3 Bed, 2 Bath

Listing# 112 Property Photo

FRBO Seasonal Rental $6,500

Windstar On Naples Bay,

3522 Haldeman Creek Drive Unit 133
Naples, FL 34113
Property Address

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Top-Floor Condo in Windstar on Naples Bay – Available December 2025 and Season 2026 2 Bedrooms | 2 Bathrooms | Private Beach Shuttle | Optional Golf Access Availability and Rates: December 2025: $5,500 per month (Golf privileges av...

1400 Sqft,
2 Bed, 2 Bath

Listing# 118 Property Photo

FRBO Annual or Seasonal Rental $7,500

Windstar On Naples Bay,

4700 Yacht Harbor Dr. 613
Naples, FL 34112
Property Address

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Luxury 3BR Condo at Windstar on Naples Bay Your premier Florida getaway begins at this ground-floor, end-unit condo situated directly on the 7th Tee Box at Windstar on Naples Bay. This peaceful retreat is currently being freshly painted and curate...

1830 Sqft,
3 Bed, 2 Bath

View All Owner Rental Listings

If you see a property you are interested in, please contact the listing agent or owner directly. Their contact information is on each listing.

Club Properties
Call: 941-444-6078
Main Office:
9040 Town Center Parkway
Lakewood Ranch, FL, 34202
United States

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The data relating to real estate for sale on this Website comes in part from the Broker Reciprocity Program (BR Program) of these sources: M.L.S. of Naples, Inc., Bonita Springs-Estero Association of REALTORS®, Southwest Florida MLS (Gulf Coast), My Florida Regional MLS DBA Stellar MLS, Sanibel and Captiva Island Association of Realtors®. Properties listed with brokerage firms other than Featured Home Listings are marked with the BR House Icon and detailed information about them includes the name of the Listing Brokers. The properties displayed may not be all the properties available through the BR Program. The data is updated every 4 hours, but can be influenced by delays from various real estate companies entering data in MLS. Some properties that appear for sale on this website may subsequently have sold or may otherwise no longer be available. All properties are subject to price or other changes without notice. For the most current information, please contact us using this form, or click on the "Request Info or Appointment" button on the search results and detailed property pages.

The source of this real property information is the copyrighted and proprietary database compilation of the © 2026 M.L.S. of Naples, Inc., © 2026 Bonita Springs-Estero Association of REALTORS®, © 2026 Southwest Florida MLS (Gulf Coast), © 2026 My Florida Regional MLS DBA Stellar MLS and © 2026 Featured Home Listings, a Florida Real Estate Brokerage. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it. Information last refreshed: 2026-08-09 00:32:38

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