Naples, FL
Windward at Regatta
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.
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.
| Date | Price (USD, excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Jul 22, 2026 | $265 | Not Available | 7 |
| Jul 23, 2026 | $265 | Not Available | 7 |
| Jul 24, 2026 | $265 | Not Available | 7 |
| Jul 25, 2026 | $265 | Not Available | 7 |
| Jul 26, 2026 | $265 | Not Available | 7 |
| Jul 27, 2026 | $265 | Not Available | 7 |
| Jul 28, 2026 | $265 | Not Available | 7 |
| Jul 29, 2026 | $265 | Not Available | 7 |
| Jul 30, 2026 | $265 | Not Available | 7 |
| Jul 31, 2026 | $265 | Not Available | 7 |
| Aug 1, 2026 | $265 | Not Available | 7 |
| Aug 2, 2026 | $265 | Not Available | 7 |
| Aug 3, 2026 | $265 | Not Available | 7 |
| Aug 4, 2026 | $265 | Not Available | 7 |
| Aug 5, 2026 | $265 | Not Available | 7 |
| Aug 6, 2026 | $265 | Not Available | 7 |
| Aug 7, 2026 | $265 | Not Available | 7 |
| Aug 8, 2026 | $265 | Not Available | 7 |
| Aug 9, 2026 | $265 | Not Available | 7 |
| Aug 10, 2026 | $265 | Not Available | 7 |
| Aug 11, 2026 | $265 | Not Available | 7 |
| Aug 12, 2026 | $265 | Not Available | 7 |
| Aug 13, 2026 | $265 | Not Available | 7 |
| Aug 14, 2026 | $265 | Not Available | 7 |
| Aug 15, 2026 | $265 | Not Available | 7 |
| Aug 16, 2026 | $265 | Not Available | 7 |
| Aug 17, 2026 | $265 | Not Available | 7 |
| Aug 18, 2026 | $265 | Not Available | 7 |
| Aug 19, 2026 | $265 | Not Available | 7 |
| Aug 20, 2026 | $265 | Not Available | 7 |
| Aug 21, 2026 | $265 | Not Available | 7 |
| Aug 22, 2026 | $265 | Not Available | 7 |
| Aug 23, 2026 | $265 | Not Available | 7 |
| Aug 24, 2026 | $265 | Not Available | 7 |
| Aug 25, 2026 | $265 | Not Available | 7 |
| Aug 26, 2026 | $265 | Not Available | 7 |
| Aug 27, 2026 | $265 | Not Available | 7 |
| Aug 28, 2026 | $265 | Not Available | 7 |
| Aug 29, 2026 | $265 | Not Available | 7 |
| Aug 30, 2026 | $265 | Not Available | 7 |
| Aug 31, 2026 | $265 | Not Available | 7 |
| Sep 1, 2026 | $265 | Not Available | 7 |
| Sep 2, 2026 | $265 | Not Available | 7 |
| Sep 3, 2026 | $265 | Not Available | 7 |
| Sep 4, 2026 | $265 | Not Available | 7 |
| Sep 5, 2026 | $265 | Not Available | 7 |
| Sep 6, 2026 | $265 | Not Available | 7 |
| Sep 7, 2026 | $265 | Not Available | 7 |
| Sep 8, 2026 | $265 | Not Available | 7 |
| Sep 9, 2026 | $265 | Not Available | 7 |
| Sep 10, 2026 | $265 | Not Available | 7 |
| Sep 11, 2026 | $265 | Not Available | 7 |
| Sep 12, 2026 | $265 | Not Available | 7 |
| Sep 13, 2026 | $265 | Not Available | 7 |
| Sep 14, 2026 | $265 | Not Available | 7 |
| Sep 15, 2026 | $265 | Not Available | 7 |
| Sep 16, 2026 | $265 | Not Available | 7 |
| Sep 17, 2026 | $265 | Not Available | 7 |
| Sep 18, 2026 | $265 | Not Available | 7 |
| Sep 19, 2026 | $265 | Not Available | 7 |
| Sep 20, 2026 | $265 | Not Available | 7 |
| Sep 21, 2026 | $265 | Not Available | 7 |
| Sep 22, 2026 | $265 | Not Available | 7 |
| Sep 23, 2026 | $265 | Not Available | 7 |
| Sep 24, 2026 | $265 | Not Available | 7 |
| Sep 25, 2026 | $265 | Not Available | 7 |
| Sep 26, 2026 | $265 | Not Available | 7 |
| Sep 27, 2026 | $265 | Not Available | 7 |
| Sep 28, 2026 | $265 | Not Available | 7 |
| Sep 29, 2026 | $265 | Not Available | 7 |
| Sep 30, 2026 | $265 | Not Available | 7 |
| Oct 1, 2026 | $265 | Available | 7 |
| Oct 2, 2026 | $265 | Available | 7 |
| Oct 3, 2026 | $265 | Available | 7 |
| Oct 4, 2026 | $265 | Available | 7 |
| Oct 5, 2026 | $265 | Available | 7 |
| Oct 6, 2026 | $265 | Available | 7 |
| Oct 7, 2026 | $265 | Available | 7 |
| Oct 8, 2026 | $265 | Available | 7 |
| Oct 9, 2026 | $265 | Available | 7 |
| Oct 10, 2026 | $265 | Available | 7 |
| Oct 11, 2026 | $265 | Available | 7 |
| Oct 12, 2026 | $265 | Available | 7 |
| Oct 13, 2026 | $265 | Available | 7 |
| Oct 14, 2026 | $265 | Available | 7 |
| Oct 15, 2026 | $265 | Available | 7 |
| Oct 16, 2026 | $390 | Available | 7 |
| Oct 17, 2026 | $390 | Available | 7 |
| Oct 18, 2026 | $390 | Available | 7 |
| Oct 19, 2026 | $390 | Available | 7 |
| Oct 20, 2026 | $390 | Available | 7 |
Amenities
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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
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
You'll save $3,000+ booking direct!
Direct
Best price
$12,500
Airbnb
$18,500
Vrbo
$15,500
Booking.com
$18,500
Lower prices, every time
Pay less than you would anywhere else. No middlemen or platform fees.
Direct line, real care
Book with the team that actually runs the property. Faster answers, better service, real accountability.
Not just a transaction
We go further for direct guests. We're building a relationship, not closing a booking.
