Entire condo

Windward at Regatta - Modern vacation destination!

Condo near Vanderbilt Beach in Naples

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Photo gallery for Windward at Regatta - Modern vacation destination!

A heated pool
Smart TV
Smart TV
Interior
Outdoor dining

Reviews

10 out of 10
Exceptional

Entire condo

3 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

Explore the area

View in a map
Naples, FL
  • Place, Vanderbilt Beach
    ‪7 min walk‬
  • Place, Pelican Bay Community Park
    ‪12 min walk‬
  • Place, Mercato
    ‪5 min drive‬
  • Airport, Fort Myers, FL (RSW-Southwest Florida Intl.)
    ‪37 min drive‬

Room options

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About the neighborhood

Naples

Vanderbilt Beach stay.Within a 15-minute walk of this Vanderbilt Beach condo, you'll find Vanderbilt Beach and Pelican Bay Community Park. Bayview Avenue Beach and Mercato are also within 2 miles (3 km).

What's nearby

  • Vanderbilt Beach - 7 min walk - 0.4 miles
  • Pelican Bay Community Park - 12 min walk - 0.7 miles
  • Bayview Avenue Beach - 20 min walk - 1.1 miles
  • Delnor-Wiggins Pass State Park - 3 min drive - 1.7 miles
  • Mercato - 5 min drive - 1.5 miles

Getting around

  • Southwest Florida Intl. Airport (RSW) - 37 min drive

Restaurants

  • ‪Chipotle Mexican Grill - ‬3 min drive
  • ‪LaPlaya Beach & Golf Resort - ‬18 min walk
  • ‪The Lobby Bar - ‬9 min walk
  • ‪Gumbo Limbo - ‬9 min walk
  • ‪Buzz's Lighthouse Restaurant - ‬10 min walk

About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

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.

Similar properties

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Communal pool
  • Heated pool
  • Hot tub

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Smart TV

Outdoor areas

  • Balcony
  • Gas grill

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Location highlights

  • Near the bay
  • On the waterfront

Things to do

  • Gym
  • Heated pool
  • Ecotours nearby
  • Fishing nearby
  • Swimming nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
Onsite 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 there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.

Property is also known as

882281

Frequently asked questions

How close is Windward at Regatta - Modern vacation destination! to the airport?

This condo is 27.3 mi (37-min drive) away from the Southwest Florida Intl. Airport (RSW) airport, the closest popular airport to the property.

How much does it cost to stay at Windward at Regatta - Modern vacation destination!?

As of Feb 26, 2026, prices found for a 1-night stay for 2 adults at Windward at Regatta - Modern vacation destination! on Mar 8, 2026 start from 1926.0, excluding 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.

Does Windward at Regatta - Modern vacation destination! have an airport shuttle?

Airport shuttle services are not available at this condo.

How close is Windward at Regatta - Modern vacation destination! to the beach?

This condo is a short 8-minute walk from Vanderbilt Beach and 7.3 mi (18-min drive) from Bonita Springs Public Beach. Don't forget your sunscreen!

Does Windward at Regatta - Modern vacation destination! offer free breakfast?

This condo does not offer free breakfast.

Is there a casino at Windward at Regatta - Modern vacation destination!?

No, there is no casino at this condo.

What time is check-in at Windward at Regatta - Modern vacation destination!?

Check-in begins at 3:00 PM.

Is there free parking at Windward at Regatta - Modern vacation destination!?

Free parking is not available at this condo.

Does Windward at Regatta - Modern vacation destination! have a pool?

Yes, there's a heated pool.

Does Windward at Regatta - Modern vacation destination! have a spa?

There are no spa services available at this condo.

How close is Windward at Regatta - Modern vacation destination! to downtown Naples?

This condo is 2 mi away from North Naples.

Windward at Regatta - Modern vacation destination! Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 1 out of 1 reviews
Rating 8 - Good. 0 out of 1 reviews
Rating 6 - Okay. 0 out of 1 reviews
Rating 4 - Poor. 0 out of 1 reviews
Rating 2 - Terrible. 0 out of 1 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Rosanne M.

Liked: Cleanliness
Stayed 7 nights in Jul 2025