Entire condo

Windward at Regatta - Modern vacation destination!

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A heated pool
Smart TV
Smart TV
Outdoor dining
Interior

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

Located in Vanderbilt Beach, this condo is a leisurely stroll from sights such as Vanderbilt Beach and Pelican Bay Community Park. The condo includes a kitchen, a balcony, and a dining area.

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.
The condo is air-conditioned and features a kitchen, 2 bathrooms, and a balcony. There's space to spread out with 3 bedrooms and a dining area. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a coffee maker, and a dining table.

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

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

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
  • Check-in: 3:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a fire extinguisher, a smoke detector, and a deadbolt lock.

Property is also known as

882281

Frequently asked questions

What's there to see within easy reach of this condo?

This condo is situated in Vanderbilt Beach within a short 8-minute walk of Vanderbilt Beach and also 13 minutes on foot from Pelican Bay Community Park. You'll also find Pelican Bay North Beach and Mercato within a short drive.

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

As of Mar 5, 2026, prices found for a 1-night stay for 2 adults at Windward at Regatta - Modern vacation destination! on Mar 8, 2026 start from $2,869, 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 parking available on site at this condo?

Yes, there is a garage.

Is this condo adjacent to a casino?

No, this condo is not connected to a casino.

Will I find an indoor pool at this condo?

No, this condo doesn't have an indoor pool; however, there is a hot tub.

What do couples enjoy most about Windward at Regatta - Modern vacation destination!?

Amenities that appeal to couples at this waterfront condo include a kitchen and a smart TV along with a heated pool.

Are there hot tubs at Windward at Regatta - Modern vacation destination!?

Yes, guests can enjoy a spa tub at this condo.

Does this condo include breakfast service?

No, this condo doesn't offer breakfast.

Will this condo allow pets to stay free of charge?

No, pets aren't allowed at this condo.

Are there connecting rooms at this condo?

No, there aren't connecting rooms at this condo.

How far is the airport from this condo?

The closest major airport to this condo is Southwest Florida Intl. Airport (RSW), which is 27.3 mi away (37 minutes by car).

Are there rooms with balconies at Windward at Regatta - Modern vacation destination!?

Yes, every condo unit at Windward at Regatta - Modern vacation destination! comes with a balcony with some featuring water views.

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