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Regatta 404 - Luxurious 3 Bedroom Weekly Vacation Rental with Amazing Amenities in Naples, FL

Condo Rental in Naples Florida

Welcome to Regatta 404, an exquisite 3 bedroom condo in Naples, FL. With top-notch amenities and a prime location, this is the ultimate destination for your dream vacation. Experience luxury and comfort like never before. Book now!

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William Raveis Florida Rentals
Connect directly with the local vacation rental manager.
Rates from
$250 / night
Additional fees may apply
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Rental overview

Why You'll Love This Rental

Regatta is a 3-bedroom, 2-bath condo in Naples, Florida, set on the bay with bay views and near the beach. With 1,635 square feet and sleeping for up to 6, it offers a roomy layout for longer stays, supported by a 7-night minimum. A lanai, on-site pool, and waterfront setting are key differentiators, along with practical conveniences like in-unit laundry and internet access.

Inside, the sleeping setup includes a king bed, twin beds, and additional beds noted as a day bed and a queen in the third bedroom. The condo includes three flat-screen TVs and a washer/dryer. Community amenities at Regatta include a pool and an exercise facility, plus an outdoor grilling area. Booking notes include a 20-day approval period, a required Tenant Evaluation application with a $150 fee, and a Saturday-to-Saturday schedule for stays between January 1 and April 30. Pets are not allowed.

Good fit for
Family Vacations
Bayfront Setting Waterfront condo with bay views.
Sleeps Six 3BR/2BA layout accommodates up to 6 guests.
Lanai Included Private lanai is included with the condo.
Pool Access Community pool is available at the Regatta complex.
No Pets Pets are not allowed.
At a glance

Property Highlights

Waterfront - BayLocation Setting
Near a BeachBeach Access
3 BedroomsBedrooms
2 Full BathroomsBathrooms
Sleeps 6Guest Capacity
1635 sq. ft.Living Space
PoolPool
Internet AccessInternet
YesWasher / Dryer
Location & nearby Explore the Area

This condo is located in Naples, Florida, in the South Gulf Coast region, with a waterfront bay setting and a bay view. The listing indicates it is near a beach, with beach distance described as 2 blocks. An important local note is that there is ongoing construction in the Vanderbilt Beach area, which may result in increased noise levels and/or traffic delays during your stay.

Plan your stay

Rates & Availability (USD)

Rates from
$250 per night
7-day minimum stay
Check current rates & availability

Live booking details are maintained by William Raveis Florida Rentals.

Check Availability

Availability Calendar

Use the calendar as a guide, then confirm current availability directly with the manager.

Available Booked
Season Nightly Weekly Monthly
PMS Rate
Oct 25, 2026 - Nov 20, 2026
Minimum Stay: 7 Days
$250 $1,750 n/a
PMS Rate
Nov 21, 2026 - Nov 27, 2026
Minimum Stay: 7 Days
$286 $2,000 n/a
PMS Rate
Nov 28, 2026 - Dec 18, 2026
Minimum Stay: 7 Days
$500 $3,000 n/a
PMS Rate
Dec 19, 2026 - Jan 01, 2027
Minimum Stay: 7 Days
$500 $3,500 n/a
PMS Rate
Jan 02, 2027 - Apr 30, 2027
Minimum Stay: 7 Days
$429 $3,000 n/a
PMS Rate
May 01, 2027 - Oct 29, 2027
Minimum Stay: 7 Days
$250 $1,750 n/a

Additional Rate Information

Email us for the most updated rates and availability and we will contact you right back.

About this rental

About This Rental

Regatta is a bayfront condo in Naples, Florida, offering 3 bedrooms and 2 full bathrooms across approximately 1,635 square feet. The home is positioned on the fourth floor of a six-story building and includes a lanai with bay views. The property sleeps up to 6 and is offered with a 7-night minimum stay.

Sleeping arrangements are listed as a king bed, twin beds, and a day bed, with additional bed details noting a queen bed in the third bedroom. For in-home comfort and downtime, the condo includes internet access, a washer/dryer, and three flat-screen TVs.

On-site and community features at Regatta include a pool and an exercise facility, along with an outdoor grilling area for meals at the complex. The listing also notes the condo is near a beach, with beach distance described as 2 blocks.

Important booking and community requirements apply. Reservations must be made at least 14 days prior to arrival, and all guests must complete a separate Regatta application through the Tenant Evaluation platform; a $150 application fee is required. The approval period is listed as 20 days. For reservations between January 1 and April 30, bookings must follow a Saturday-to-Saturday schedule. The Vanderbilt Beach area is noted as having ongoing construction that may increase noise levels and/or cause traffic delays. Pets are not allowed.

Discover the perfect coastal escape at this beautiful 3BR/2BA retreat, located on the bay and just a short stroll from Vanderbilt Beach. This well-appointed condo has everything you need for a comfortable stay.
Regatta offers amazing amenities that will make your vacation unforgettable. Cool off in the tropical waterfall pool, let the kids splash around in their own pool, unwind in the hot tub, or stay fit in the on-site fitness rooms. The outdoor grilling area is perfect for BBQ evenings, and tennis lovers will enjoy the courts just up the street at Pelican Bay Community Park. All of this is just a walk away from the sandy shores of Vanderbilt Beach and Delnor-Wiggins State Park, ranked among the top 10 beaches in the US. Spend your days relaxing, swimming, and enjoying water sports before capping off the evening with breathtaking sunsets. It's the perfect place to make lasting family memories!

All reservations between January 1 and April 30 must follow a Saturday-to-Saturday booking schedule. For special requests outside of this timeframe, please contact us directly.

Reservations must be made at least 14 days prior to arrival. Any reservation booked online within 14 days of the arrival date will be automatically cancelled.

Please note that all guests are required to complete a separate application for Regatta, processed through the TenantEvaluation online platform. A $150 application fee applies and must be paid directly through the platform.

Important Notice: There is ongoing construction in the Vanderbilt Beach area, which may lead to increased noise levels and/or traffic delays.

All information provided is deemed reliable but not guaranteed.

For more information, contact Lesley Garlock at 239-289-1351 or by email to lesley.garlock@raveis.com.
Things to enjoy

Activities and Special Interests

This property provides access to the following activities and special interests:

Beach
Biking
Boating
Canoeing
Family Vacations
Fishing
Deep Sea Fishing
Fly Fishing
Golfing
Hiking
Hunting
Kayaking
Ocean
Resorts
Sailing
Scuba Diving
State National Parks
Surfing
Wind Surfing
What's included

Property Amenities

Featured Amenities

Grill
Internet Access
Washer/Dryer
Pool

Property Features

Lanai

Other Property Amenities

Weekly- Season: $3,000 (holiday rates higher) - $3500/week
Weekly- Off Season: $1,750 (holiday rates higher)
Minimum Nights: 7
Bldg. Complex Name: Regatta
Approval Period: 20 Days
Application Fee Req.: $150 - TENANT EVALUATION
Pets: Not Allowed
View: Bay
Beach Distance: 2 Blocks
Walk-To-Beach
Bedroom/Bathroom: 3BR/2BA
Bed Size 1st/Master: King
Bed Size 2nd Rm: Twins
Bed Size 3rd Rm: Queen
Exercise Facility: Community
Square Footage, Est.: 1635/1785
TVs/VCR/DVD: 3 Flat Screen
Rear Exposure: N
Floor/Bldg Height: 4/6

Come enjoy your next vacation at this great condo rental in Naples Florida! This 3 bedroom condo is great for any group of family or friends, and pets! This community is pet friendly! You can enjoy plenty of things while staying at this condo rental, such as a fitness center where you can get a workout in, a pool to have fun in, a dock area for your boats, and so much more! When travelers book with William Raveis/South Bay Team, you experience outstanding service and great rates along with a safe place to stay for you and your guests while on vacation! 

Regatta 404 in Naples, FL, sets a new standard for upscale vacation rentals with its luxurious 3-bedroom accommodation and superb amenities. This exclusive property offers a perfect blend of sophistication and comfort, ideal for discerning travelers seeking a refined retreat. With its prime location and exquisite features, Regatta 404 presents an unparalleled opportunity for a memorable stay in the heart of Naples. Discover how this remarkable vacation rental can elevate your travel experience and provide a unique escape unlike any other.

Property Overview

Boasting a luxurious 3-bedroom vacation condo nestled in the heart of Naples, FL, this property offers a serene retreat for up to 6 guests seeking comfort and relaxation amidst upscale amenities and a prime location near Vanderbilt Beach and Delnor-Wiggins State Park. The interior design exudes elegance and sophistication, with carefully curated furnishings and decor creating a welcoming ambiance. Guests can enjoy easy beach access, allowing for leisurely strolls along the pristine shoreline or exciting water activities. The condo's proximity to Vanderbilt Beach and Delnor-Wiggins State Park ensures endless opportunities for sun-soaked days and memorable moments by the sea. Whether unwinding indoors or exploring the nearby coastal attractions, this vacation rental provides the perfect blend of luxury and convenience for a truly indulgent getaway.

Bedroom Configuration

Nestled within this luxurious 3-bedroom vacation condo in Naples, FL, the bedroom configuration offers a comfortable and accommodating layout for guests seeking a restful stay. The master bedroom boasts a regal King bed, complemented by tasteful interior decor that exudes elegance and tranquility. The second bedroom features two cozy twin beds, perfect for children or friends traveling together. Additionally, the third bedroom provides a Queen bed for added convenience. Each room is thoughtfully designed to ensure a peaceful night's sleep, with plush bedding and modern furnishings enhancing the overall ambiance. Whether unwinding after a day of exploration or enjoying a lazy morning, the sleeping arrangements cater to a variety of preferences, promising a rejuvenating vacation experience.

Amenities Offered

Enhancing the overall experience, this vacation condo in Naples, FL offers a range of amenities designed to promote comfort and relaxation for guests.

  • Pet friendly accommodations for furry companions to join the vacation
  • On-site grilling area perfect for outdoor cooking experiences
  • Fishing pier available for guests to enjoy recreational activities
  • Access to a fitness center for those wanting to stay active during their stay

These amenities cater to guests seeking a balance of relaxation and activities, ensuring an enjoyable and memorable vacation experience in Naples, FL. Whether unwinding with a barbecue by the grilling area or trying your hand at fishing from the pier, there are options for everyone to make the most of their stay at Regatta 404.

Rates and Booking Details

For detailed information on rates and booking procedures for the luxurious vacation rental in Naples, FL, please contact the property management team via email. The weekly rates for this splendid 3-bedroom condo are $3,000 during the peak season and $1,400 in the off-season, with higher rates applying during holidays. A minimum stay of 7 nights is required, and there is an application fee of $150. The property is pet-friendly, but it's advisable to seek pet policy clarification directly from the management team. Enjoy stunning views of the bay just 2 blocks from the beach, along with access to community amenities such as a fitness center and pool. Book through William Raveis/South Bay Team for competitive rates and excellent service.

Nearby Attractions

Explore the vibrant array of nearby attractions that complement the luxurious vacation rental in Naples, FL, offering guests a diverse range of activities and experiences to enjoy during their stay.

  1. Beach Activities: Vanderbilt Beach and Delnor-Wiggins State Park are just a stone's throw away, perfect for sunbathing, swimming, and water sports.
  2. Dining Options: Indulge in a culinary adventure with a plethora of dining choices ranging from upscale seafood restaurants to cozy cafes, ensuring a delightful gastronomic experience.
  3. Shopping: Discover trendy boutiques and upscale shops for a day of retail therapy, all within a short distance from the vacation rental.
  4. Outdoor Recreation: Explore nearby tennis courts, theaters, and other recreational facilities for a fun-filled vacation experience.

Community Features

The community features of this luxurious vacation rental in Naples, FL offer an array of amenities designed to enhance the overall guest experience. Embracing pet-friendly policies, guests can enjoy their stay with their furry companions. The community provides ample opportunities for recreational activities, including a fitness center to keep active during your vacation. Additionally, there are facilities such as a grilling area for outdoor cooking enthusiasts and a fishing pier for those looking to engage in leisurely pursuits. Whether you seek relaxation or adventure, these community features cater to a variety of preferences, ensuring a memorable and fulfilling stay for all guests at Regatta 404.

Contact Information

Contact the property management team for the luxurious vacation rental in Naples, FL via the provided email address for updated rates and availability.

  • Pet-Friendly Policies: Enjoy your vacation with your furry friends as this rental offers pet-friendly accommodations.
  • Customer Service Satisfaction: Experience exceptional customer service from the property management team to ensure a smooth and enjoyable stay.
  • Quick Response Time: Expect prompt responses to your inquiries and booking requests to assist you efficiently.
  • Detailed Information: Receive all the necessary details about the property, amenities, and booking process to make an informed decision.

For more information on rates, availability, and any inquiries, reach out to the property management team through the provided email address.

Directions and Accessibility

Navigating to the luxurious vacation rental in Naples, FL is straightforward and convenient, ensuring easy accessibility for guests seeking a relaxing and upscale getaway experience. Guests arriving by car will appreciate the designated parking spaces available on-site, providing a hassle-free experience upon arrival. For those utilizing local transportation, the property's proximity to various amenities and attractions in Naples, FL makes it easily accessible. The vacation rental's strategic location allows guests to explore nearby destinations like Vanderbilt Beach and Delnor-Wiggins State Park with ease. Additionally, the property's central position offers convenient access to shops, restaurants, and theaters, enhancing the overall convenience and enjoyment of guests' stay.

Frequently Asked Questions

Are Beach Chairs and Umbrellas Provided for Guests to Use During Their Stay at Regatta 404?

Beach chairs and umbrellas are not provided for guests at Regatta 404. However, guests have the option to rent poolside cabanas for relaxation and comfort while enjoying the amenities. Water sports rentals are available for those seeking outdoor activities. Take advantage of the nearby beach and state park for a fun-filled vacation experience in Naples, FL. Enjoy the freedom to explore various recreational options during your stay.

Is There a Grocery Delivery Service Available for Guests Staying at the Vacation Condo?

For added convenience, guests staying at the vacation condo can utilize a grocery delivery service. This amenity allows for a seamless experience, providing guests with the option to have groceries delivered directly to their rental unit. This service enhances the overall comfort and relaxation of the stay, ensuring that guests have easy access to essentials without the need to leave the property. It is a convenient feature that adds to the convenience of the vacation rental experience.

Are Bicycles Available for Rent at or Near the Property for Guests to Explore the Area?

Bike rentals are available near the property, offering guests the opportunity to explore the area through local trails and scenic routes. Cycling tours can be arranged to experience the beauty of Naples, FL. Embrace the freedom of discovering the surroundings at your own pace while enjoying the fresh air and stunning views. Explore the nearby attractions and amenities effortlessly with bicycles for rent, enhancing your vacation experience.

Is There a Shuttle Service Provided for Guests to Access Nearby Attractions and Restaurants?

While shuttle services are not provided at the property, guests have convenient access to nearby attractions such as Vanderbilt Beach, Delnor-Wiggins State Park, shops, tennis courts, restaurants, and theaters. The property's prime location allows for easy exploration of the area at one's leisure. Enjoy the freedom to discover the beauty and amenities Naples, FL has to offer, all within close proximity to the vacation rental.

Are There Any Special Events or Activities Organized for Guests Staying at Regatta 404 During Their Stay?

Special events and activities are not organized for guests at this accommodation. However, guests can enjoy a range of amenities like the on-site fitness center, grilling area, and fishing pier. For personalized services or recommendations, guests can inquire about guest accommodations and concierge services available during their stay. The focus is on providing a comfortable and relaxing environment for guests to enjoy their vacation in Naples, FL.

Helpful details

Frequently Asked Questions

Regatta is located in Naples, Florida.

Regatta accommodates up to 6 guests.

3 Bedrooms and 2 Full Bathrooms.

The listed beach access for Regatta is Near a Beach.

Yes. The property lists Pool.

The property lists a 7-night minimum stay.
Local management

Professionally Managed By

William Raveis Florida Rentals
In business since 2003
View Manager Profile

Questions about this rental?

Connect directly with William Raveis Florida Rentals for current rates, availability, and local assistance.

Contact Reservations and Guest Services at William Raveis - South Bay Team
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Property reference
#130836 · Regatta
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