Naples, FL

Windward at Regatta

3 bedrooms3 beds2 baths6 guestsNew

About the property

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.

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.

Availability & Pricing

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

DatePrice (USD, excl. fees and taxes)AvailabilityMin Stay (nights)
Jul 22, 2026$265Not Available7
Jul 23, 2026$265Not Available7
Jul 24, 2026$265Not Available7
Jul 25, 2026$265Not Available7
Jul 26, 2026$265Not Available7
Jul 27, 2026$265Not Available7
Jul 28, 2026$265Not Available7
Jul 29, 2026$265Not Available7
Jul 30, 2026$265Not Available7
Jul 31, 2026$265Not Available7
Aug 1, 2026$265Not Available7
Aug 2, 2026$265Not Available7
Aug 3, 2026$265Not Available7
Aug 4, 2026$265Not Available7
Aug 5, 2026$265Not Available7
Aug 6, 2026$265Not Available7
Aug 7, 2026$265Not Available7
Aug 8, 2026$265Not Available7
Aug 9, 2026$265Not Available7
Aug 10, 2026$265Not Available7
Aug 11, 2026$265Not Available7
Aug 12, 2026$265Not Available7
Aug 13, 2026$265Not Available7
Aug 14, 2026$265Not Available7
Aug 15, 2026$265Not Available7
Aug 16, 2026$265Not Available7
Aug 17, 2026$265Not Available7
Aug 18, 2026$265Not Available7
Aug 19, 2026$265Not Available7
Aug 20, 2026$265Not Available7
Aug 21, 2026$265Not Available7
Aug 22, 2026$265Not Available7
Aug 23, 2026$265Not Available7
Aug 24, 2026$265Not Available7
Aug 25, 2026$265Not Available7
Aug 26, 2026$265Not Available7
Aug 27, 2026$265Not Available7
Aug 28, 2026$265Not Available7
Aug 29, 2026$265Not Available7
Aug 30, 2026$265Not Available7
Aug 31, 2026$265Not Available7
Sep 1, 2026$265Not Available7
Sep 2, 2026$265Not Available7
Sep 3, 2026$265Not Available7
Sep 4, 2026$265Not Available7
Sep 5, 2026$265Not Available7
Sep 6, 2026$265Not Available7
Sep 7, 2026$265Not Available7
Sep 8, 2026$265Not Available7
Sep 9, 2026$265Not Available7
Sep 10, 2026$265Not Available7
Sep 11, 2026$265Not Available7
Sep 12, 2026$265Not Available7
Sep 13, 2026$265Not Available7
Sep 14, 2026$265Not Available7
Sep 15, 2026$265Not Available7
Sep 16, 2026$265Not Available7
Sep 17, 2026$265Not Available7
Sep 18, 2026$265Not Available7
Sep 19, 2026$265Not Available7
Sep 20, 2026$265Not Available7
Sep 21, 2026$265Not Available7
Sep 22, 2026$265Not Available7
Sep 23, 2026$265Not Available7
Sep 24, 2026$265Not Available7
Sep 25, 2026$265Not Available7
Sep 26, 2026$265Not Available7
Sep 27, 2026$265Not Available7
Sep 28, 2026$265Not Available7
Sep 29, 2026$265Not Available7
Sep 30, 2026$265Not Available7
Oct 1, 2026$265Available7
Oct 2, 2026$265Available7
Oct 3, 2026$265Available7
Oct 4, 2026$265Available7
Oct 5, 2026$265Available7
Oct 6, 2026$265Available7
Oct 7, 2026$265Available7
Oct 8, 2026$265Available7
Oct 9, 2026$265Available7
Oct 10, 2026$265Available7
Oct 11, 2026$265Available7
Oct 12, 2026$265Available7
Oct 13, 2026$265Available7
Oct 14, 2026$265Available7
Oct 15, 2026$265Available7
Oct 16, 2026$390Available7
Oct 17, 2026$390Available7
Oct 18, 2026$390Available7
Oct 19, 2026$390Available7
Oct 20, 2026$390Available7

Amenities

Waterfront
Beach access
Gym
Air conditioning
Dryer
Washer
Garage
Hair dryer

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Where you'll be

Naples, FL, 34108, US

Immerse yourself in the sophisticated coastal lifestyle of Naples, where pristine nature meets upscale urban convenience. Explore the nearby Delnor-Wiggins Pass State Park for stunning white-sand beaches and scenic trails, or stroll through the vibrant dining, entertainment, and shopping hub at Mercato. Minutes away, you can experience world-class cultural performances at Artis—Naples, browse high-end boutiques at the Waters

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

Things to know

Cancellation policy

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
No pets allowed.
No parties or events.

Safety & security

Check-in after 3:00 PM.
Check-out before 10:00 AM.
Maximum 6 guests.