Entire condo

Windward at Regatta - Modern vacation destination!

Photo gallery for Windward at Regatta - Modern vacation destination!

A heated pool
Interior
Smart TV
A spacious living room with a large sliding glass door leading to an outdoor area, a white sofa, a wooden coffee table, and a framed landscape painting on the wall.
Outdoor dining

Reviews

7.0 out of 10
Good

Entire condo

3 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Explore the area

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

Room options

Similar properties

About the area

Naples

With a stay at this condo in Naples (Vanderbilt Beach), you'll be within a 15-minute drive of Vanderbilt Beach and Fifth Avenue South. .This condo is 7.3 mi (11.7 km) from Bonita Springs Public Beach and 8 mi (12.8 km) from Naples Beach.

What's nearby

  • Vanderbilt Beach - 11 min walk - 0.9 km
  • Pelican Bay Community Park - 13 min walk - 1.2 km
  • Seabreeze Avenue Beach - 2 min drive - 1.7 km
  • Bayview Avenue Beach - 3 min drive - 1.7 km
  • Mercato - 5 min drive - 2.4 km

Getting around

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

Restaurants

  • ‪Chipotle Mexican Grill - ‬3 min drive
  • ‪LaPlaya Beach & Golf Resort - ‬18 min walk
  • ‪Gumbo Limbo - ‬9 min walk
  • ‪Bicyclette Cookshop - ‬19 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.
Make yourself comfortable in this air-conditioned condo, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Complimentary wireless internet access keeps you connected, and a Smart television is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.
Don't miss out on recreational opportunities including a hot tub and a fitness center.
Guests will find features like internet access and onsite parking.

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Communal pool
  • Heated pool
  • Hot tub

Internet

  • Available in the condo: Free WiFi

Parking and transport

  • Onsite parking options include a garage

Kitchen

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

  • Smoke-free property

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

Pets not allowed

Children and extra beds

Children are welcome

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

Property is also known as

882281

Windward at Regatta - Modern vacation destination! Reviews

Reviews

7.0

Good

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

8.0/10

Cleanliness

Reviews

4/10 Poor

Lee G.

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!
Stayed 14 nights in Mar 2026

10/10 Excellent

Rosanne M.

Liked: Cleanliness
Stayed 7 nights in Jul 2025