[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire condo # Windward at Regatta - Modern vacation destination! Waterfront condo with a fitness center and a hot tub ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107970000/107969300/107969262/76b79c0d.jpg?impolicy=resizecrop&rw=598&ra=fit) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107970000/107969300/107969262/431384fd.jpg?impolicy=resizecrop&rw=297&ra=fit) ![A heated pool](https://images.trvl-media.com/lodging/108000000/107970000/107969300/107969262/9c719b9c.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Smart TV](https://images.trvl-media.com/lodging/108000000/107970000/107969300/107969262/ee33cd4c.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Smart TV](https://images.trvl-media.com/lodging/108000000/107970000/107969300/107969262/b21cd9ed.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location Regatta at Vanderbilt Beach offers a resort-style retreat with modern coastal furnishings. Unwind in the tropical waterfall pool, relax on your oversized balcony overlooking the Bay, or enjoy a workout at the fitness center and then lounge by the lap pool. 10 Exceptional ### Entire condo 3 bedrooms2 bathroomsSleeps 6 ## Popular amenities - Hot tub - Parking available - Dryer - Washer - Pool - Gym ## Add dates for prices Check-in Check-out Travellers ## 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. ## 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 ## Similar properties ![A heated pool](https://images.trvl-media.com/lodging/34000000/33250000/33245100/33245052/49d7973b.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Naples Vanderbilt Beach-beautiful Updated-walk to the beach Vanderbilt Beach - Pool - Hot tub - Kitchen - Washer 9.8 Exceptional 66 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-25&endDate=2025-10-26&selected=33245052&PinnedHotelID=33245052&HadPinnedHotel=true®ionId=-1&adults=2) ![Pool](https://images.trvl-media.com/lodging/107000000/106030000/106021600/106021575/3792c021.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Regatta -Resort Style: 3BR/2BA -Lanai w/dining/conversational seating/pool view Vanderbilt Beach - Pool - Kitchen - Washer - Dryer 10 Exceptional 7 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-25&endDate=2025-10-26&selected=106021575&PinnedHotelID=106021575&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/65000000/65000000/64994400/64994335/6a1b8a6a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Directly across Ritz Carlton Naples Beach Resort!!! Vanderbilt Beach - Pool - Kitchen - Washer - Dryer 9.0 Wonderful 30 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-25&endDate=2025-10-26&selected=64994335&PinnedHotelID=64994335&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach](https://images.trvl-media.com/lodging/79000000/78660000/78655400/78655387/bb2d78d0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Beautiful 3-bedroom condo walking distance to the beach - REG 4-PH4 Vanderbilt Beach - Living/dining area [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-25&endDate=2025-10-26&selected=78655387&PinnedHotelID=78655387&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach](https://images.trvl-media.com/lodging/45000000/44130000/44129400/44129368/43d8ac4f.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Regatta - William Raveis Rentals Vanderbilt Beach - Pool - Hot tub - Kitchen - Washer 10 Exceptional 1 review [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-25&endDate=2025-10-26&selected=44129368&PinnedHotelID=44129368&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor dining](https://images.trvl-media.com/lodging/85000000/84740000/84738200/84738135/976eca25.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Newly Remodeled Condo, Steps to the Beach Vanderbilt Beach - Pool - Kitchen - Washer - Dryer 10 Exceptional 19 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-25&endDate=2025-10-26&selected=84738135&PinnedHotelID=84738135&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99450000/99444000/99443920/56e8a8a3.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Luxurious condo with on-site pool, private extended balcony, & W/D Vanderbilt Beach - Pool - Kitchen - Washer - Dryer 10 Exceptional 4 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-25&endDate=2025-10-26&selected=99443920&PinnedHotelID=99443920&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/67000000/66850000/66847500/66847447/76c2bbac.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Your paradise awaits! Premier 2+den condo just steps to Vanderbilt Beach Vanderbilt Beach - Pool - Kitchen - Washer - Dryer 9.6 Exceptional 15 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-25&endDate=2025-10-26&selected=66847447&PinnedHotelID=66847447&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/106000000/105950000/105945900/105945802/5ee7b8c4.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Perfect Getaway! Naples, Walk To Vanderbilt Beach - Immaculate! Vanderbilt Beach - Pool - Kitchen - Washer - Dryer 10 Exceptional 3 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-25&endDate=2025-10-26&selected=105945802&PinnedHotelID=105945802&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach](https://images.trvl-media.com/lodging/45000000/44040000/44036100/44036020/b1d7f615.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### RELAX, UNWIND, AND ENJOY. Vanderbilt Beach - Hot tub - Kitchen - Washer - Dryer 10 Exceptional 2 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-25&endDate=2025-10-26&selected=44036020&PinnedHotelID=44036020&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Contactless check-in available ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions ### Pets Pets not 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 ### Property is also known as 882281 ## About the area Located on the waterfront, this condo is in Vanderbilt Beach, a neighborhood in Naples. Fifth Avenue South and Coconut Point Mall are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Vanderbilt Beach and Bonita Springs Public Beach. Naples Zoo at Caribbean Gardens and Naples Pier are not to be missed. Discover the area's water adventures with fishing and swimming nearby, or enjoy the great outdoors with ecotours. [Visit our Naples travel guide](https://www.expedia.ca/Naples.dx602724) [View more Condo rentals in Naples](https://www.expedia.ca/Naples-Condos.d602724-aaCondos.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C26.25369%2C-81.81767&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=GRjEZ1sTXSig9iYuCSgCs1uopuk=) Naples, FL ### What's nearby - Vanderbilt Beach - 7 min walk - 0.7 km - Mercato - 3 min drive - 2.4 km - Delnor-Wiggins Pass State Park - 4 min drive - 2.8 km - Tiburon Golf Club - 7 min drive - 6.6 km - Clam Pass Park - 14 min drive - 5.5 km ### Getting around - Southwest Florida Intl. Airport (RSW) - 37 min drive ### Restaurants - ‪LaPlaya Beach & Golf Resort - ‬18 min walk - ‪The Lobby Bar - ‬9 min walk - ‪Tacos And Tequila - ‬3 min drive - ‪Inn at Pelican Bay - ‬2 min drive - ‪The Turtle Club - ‬9 min walk ## Frequently asked questions ### Does Windward at Regatta - Modern vacation destination! have a pool? > Yes, this property has a pool. Pool types include heated pools. ### Is Windward at Regatta - Modern vacation destination! pet-friendly? > No, pets are not allowed at this property. ### Where is Windward at Regatta - Modern vacation destination! located? > Located in Vanderbilt Beach, this condo building is within a 15-minute walk of Vanderbilt Beach and Pelican Bay Community Park. Bayview Avenue Beach and Seabreeze Avenue Beach are also within 1 mi (2 km). ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Windward at Regatta - Modern vacation destination! Reviews 10 ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.[More information](https://www.expedia.ca/lp/b/content-guidelines) ### 10 Cleanliness ### 10 Location 10 - Excellent 1 8 - Good 0 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10/10 Excellent #### Rosanne M. Aug 9, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy ##### Rosanne M. 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