Windward at Regatta - Modern vacation destination!
Regatta at Vanderbilt Beach is a resort style condo complex ideally located just two blocks to Vanderbilt Beach, home of the Ritz Carlton Naples and one of the area's most popular beaches for recreation. Unit 602 beautiful coastal modern furnishings. The primary bedroom features a king size bed with en-suite bathroom and boasts a fantastic oversized balcony with direct views of the Bay! The Regatta pool area offers lounge chairs, a tropical waterfall pool, lap pool, spa/hot tub, and a poolside tiki hut complete with a kitchen, ice maker, and two gas grills. A fitness center is located adjacent to the pool area. Less than half a mile's walk lands you at the entrance to Vanderbilt Beach, immediately adjacent to the Ritz Carlton, and convenient to beachfront dining destinations including the Turtle Club and Baleen at LaPlaya, and casual bayfront dining at Buzz's Lighthouse. Regatta is also less than 2 miles from the outdoor dining and shopping complex Mercato, which has a Whole Foods and the Pavilion Plaza with a great movie theater and many more restaurants and shops.
***CONDO APPLICATION: This condo requires that all rentals are approved by the condo association. The application packet will be emailed to you to complete shortly after booking and does involve a background check. The association will charge you $150 for the application processing. The management company requires 20 days to approve applications, so last minute bookings cannot be accepted.
The Holiday Life is a full service luxury vacation and seasonal rental management company with an expansive portfolio - from beachfront, to downtown and amenity rich communities throughout Naples and Marco Island. Our team is here to assist in every step of planning your experience from choosing the perfect rental, pre arrival planning, dedicated concierge services and 24/7 support during your stay. We look forward to the opportunity to host you!
RENTAL PURPOSE: This property is intended for single-family and transient guest rentals only - any requests for work crews require specific approval prior to booking. No commercial vehicles or work trucks may be parked on site.
COMMERCIAL USE: Commercial and/or business use of the property is not allowed, including commercial photography or filming.
MINIMUM AGE REQUIREMENT: Primary guest whose name is associated with this booking must be at least 25 years of age and must be present for the duration of the reservation.
GUEST LIST: A guest list including full names and ages of all people who will be staying overnight must be provided in writing at least 24 hours to the guest(s) arrival.
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
About the area
Naples
Located on the waterfront, this condo is in Vanderbilt Beach, a neighbourhood in Naples. Shoppers can check out Fifth Avenue South, while everyone can enjoy the natural beauty of Vanderbilt Beach and Bonita Springs Public Beach. Sun N Fun Lagoon and Golf Safari Mini Golf are also worth visiting. Discover the area's water adventures with fishing and swimming nearby, or enjoy the great outdoors with ecotours.
Naples, FL
What's nearby
Vanderbilt Beach - 11 min walk - 0.9 km
Pelican Bay Community Park - 12 min walk - 1.0 km
Seabreeze Avenue Beach - 2 min drive - 2.1 km
Bayview Avenue Beach - 3 min drive - 1.7 km
Mercato - 6 min drive - 2.4 km
Getting around
Fort Myers, FL (RSW-Southwest Florida Intl.) - 37 min drive
Restaurants
Chipotle Mexican Grill - 3 min drive
LaPlaya Beach & Golf Resort - 18 min walk
Bicyclette Cookshop - 19 min walk
Gumbo Limbo - 9 min walk
Buzz's Lighthouse Restaurant - 10 min walk
Frequently asked questions
Does Windward at Regatta - Modern vacation destination! have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Windward at Regatta - Modern vacation destination!?
As of 14 May 2026, prices found for a 1-night stay for 2 adults at Windward at Regatta - Modern vacation destination! on 16 September 2026 start from NZ$707, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Windward at Regatta - Modern vacation destination! pet-friendly?
No, pets are not allowed at this property.
How much is parking at Windward at Regatta - Modern vacation destination!?
On-site parking is available at the property.
What time is check-in at Windward at Regatta - Modern vacation destination!?
Check-in begins at 3:00 PM.
What time is check-out at Windward at Regatta - Modern vacation destination!?
Checkout is at 10:00 AM.
Where is Windward at Regatta - Modern vacation destination! located?
Located in Vanderbilt Beach, this condo building is within a 15-minute walk of Vanderbilt Beach and Pelican Bay Community Park. Bayview Avenue Beach and Mercato are also within 2 miles (3 km).
Reviews
7.0
Good
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
WiFi wasn’t working. Multiple lightbulbs out. Not enough chairs around table. Electric cords exposed. No instructions for ceiling fans. Not enough beach towels Loved the location, but the unit was not adequately prepared for guests. I expected more given the price!