Listed on 03/31/2026

Listed by Mari Vesci

Days on market: 23

Luxury Penthouse Living at Vanderbilt Beach Furnished 3 bedroom, 3 bathroom penthouse in Regatta with double car garage is just moments from the white sands of Vanderbilt Beach. Available April 1st for annual rental, this residence offers sweeping water views and exceptional privacy from its top floor vantage point. Light-filled living spaces with 9 ft ceilings is open to a large screened lanai perfect for enjoying morning coffee, sunsets, and peaceful waterfront scenery. Regatta is a sought-after gated community with resort-style pool and spa, party room, fitness center and more. Unbeatable location across from the Ritz. Just minutes from Mercato’s dining, shopping, and entertainment venues! This exceptional residence delivers the best of the Naples coastal living.

Listed on 10/24/2025

Listed by Robert Alpizar

Days on market: 181

Property Status: Active ** AVAILABLE January and April of 2026 - 15 Day Minimum only! ** Escape Winter in Style, Your Naples Beach Retreat Awaits! Trade snow for sunshine and discover the ultimate coastal escape in this exquisite 10th-floor residence just steps from the powdery sands of Vanderbilt Beach. Perfectly positioned across from the iconic Ritz-Carlton Naples, this elegant end unit offers a front-row seat to the best of Florida's luxurious beachside living. Wake up each morning to sweeping panoramic views of the Gulf and Bay that stretch endlessly before you. The open-concept living and dining areas flow effortlessly together, ideal for intimate gatherings, sunset cocktails, or simply relaxing in the warmth of your sunlit surroundings. The primary suite is a tranquil sanctuary featuring private balcony access-perfect for savoring your morning coffee as the water shimmers in the distance. Two additional guest rooms provide both comfort and flexibility, making this the perfect getaway for couples, families, or friends seeking a stylish coastal retreat. Step outside and immerse yourself in the resort-style amenities of Regatta-where tropical waterfalls, a sparkling lagoon pool, lap pool, jacuzzi, fitness center, and outdoor grills create the feeling of a private resort. When you're ready to explore, stroll to the beach for a swim or a leisurely sunset walk, or head just two miles to Mercato, where fine dining, boutique shopping, and vibrant nightlife await. Whether you're escaping the chill of northern winters or simply craving endless summer days, this luxury Naples retreat offers everything you need to unwind, recharge, and experience the warmth of paradise. (Available for Winter of 2026) Office Phone: (239) 438-1102 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 07/08/2025

Listed by Lesley Garlock

Days on market: 289

Property Status: Active Beautiful upscale condominium on the 5th floor with magnificent views of Vanderbilt Bay and a glimpse of the Gulf of Mexico. This 3 bedroom, 3 bath apartment has everything you want in a vacation residence: brand new stainless steel appliances; hardwood floors in the bedrooms and ceramic tile in the living areas, baths and lanai; 6 televisions (including a large screen high definition Samsung in the living room); and wireless internet. The open floor plan is spacious and the location is perfect: just a short walk to the Gulf and Vanderbilt Beach, where you can enjoy the famous Naples' sunsets as well as wonderful beachfront dining at the Ritz Carlton, Turtle Club and La Playa. Designed as a resort style community, Regatta offers amazing on-site amenities, such as a fitness center, poolside grill and picnic area, furnished social room with built-in media center, fishing piers, boat docks, electronic gated entry, tropical waterfall pool and lap pool. Just a short drive up Vanderbilt Beach Road from Regatta are numerous fine restaurants, tennis courts at the Pelican Bay Community Park, plus movie theaters, upscale shopping, dining and dancing at the fabulous new Mercato complex. Office Phone: (239) 594-2226 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 01/10/2026

Listed by Tony Blaskis

Days on market: 103

Property Status: Active Vanderbilt Beach Area-Completely Renovated- Walking Distance to the Beach! Regatta is one of the most sought-after rental properties in Naples. The location on the Bay has shopping, restaurants, and a white sandy beach -- all within walking distance! This beautiful 3/3 condo has many upgrades from the tile flooring to the granite countertops,. Also enjoy a unique 3rd floor-only extended deck off the lanai with steps leading down to the lap pool, overlooking the bay. New flatscreen TVs, Blue-Ray, iPod Station stereo and Wi-Fi. Help keep up with the modern day tech you would expect to find at home. Designed as a resort style community, Regatta offers amazing on-site amenities such as a fitness center, poolside grill and picnic area, furnished social room with built in media center, fishing piers, boat docks electronic gated entry, tropical waterfall pool and lap pool. Walk to nearby restaurants at the Ritz Carlton, Turtle Club, The Lighthouse and La Playa. Drive up the street to even more fine restaurants plus movie theaters, upscale shopping and more at the fabulous new Mercato, Pelican Bay Marketplace, or Pavilion Shops. Office Phone: (239) 594-2226 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 07/08/2025

Listed by Lesley Garlock

Days on market: 289

Property Status: Active Enjoy the best of coastal living in this spacious 3-bedroom, 3-bathroom condominium, perfectly situated in the desirable Vanderbilt Beach area-just a short stroll from the white sand beaches and breathtaking sunsets over the Gulf. This inviting condo has everything you need for a relaxing and memorable stay in paradise, including a fully equipped kitchen, plush linens and towels, beach essentials, and more. Located within the resort-style community of Regatta, guests can take advantage of top-tier amenities such as a tropical waterfall pool, lap pool, fitness center, poolside grill and picnic area, and secure electronic gated entry. Take a leisurely 5-minute walk to the beach for swimming, paddleboarding, or simply soaking in the serene beauty of the shoreline. You'll also be within walking distance of iconic local dining at The Ritz-Carlton, Turtle Club, The Lighthouse, and LaPlaya's Baleen. A short drive brings you to even more upscale shopping, dining, and entertainment options at Mercato, Pelican Bay Marketplace, and the Pavilion Shops, complete with boutique stores, restaurants, and movie theaters. Office Phone: (239) 594-2226 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 07/08/2025

Listed by Lesley Garlock

Days on market: 289

Property Status: Active Located on Vanderbilt Bay at 400 Flagship Drive, Unit 905, Naples, FL 34108, this lovely nautical themed condo has everything that you will need to enjoy your time in PARADISE! Recently refreshed to deliver a comfortable and coastal-beachy flair. Freshly painted, new flat screen TV, lighting fixtures, linens and accessories. The warmth and coziness of the master and guest quarters are complemented by new bedding draped in luxurious linens. Gathering space flows seamlessly to a outdoor lanai supplying spectacular Gulf views. Designed as a resort style community, Regatta offers amazing on-site amenities such as a fitness center, poolside grill and picnic area, furnished social room with built in media center, boat docks, perfect for fishing, electronic gated entry, tropical waterfall pool and lap pool. Just steps to white sandy beaches including Delnor-Wiggins State Park recently named one of the Top Ten Beaches in the US. Walk to nearby restaurants at the Ritz Carlton, Turtle Club, The Lighthouse and La Playa. Drive up the street to even more fine restaurants plus movie theaters, and upscale shopping at the fabulous Mercato, Pelican Bay Marketplace or Pavilion Shops. Office Phone: (239) 594-2226 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 03/30/2026

Listed by Domenico Ceruzzi

Days on market: 24

Property Status: Active Ready for the 2027 Season! Sunshine filled END UNIT 3bds-2bths, coastal decor, SW lanai with views of Gulf sunsets and Bay waters; High Speed WiFi /Cable; assigned covered parking space and abundant guest parking. REGATTA is a luxury, gated community on the Bay, across from the RITZ CARLTON; a short walk to VANDERBILT BEACH white sand and its beach side restaurants. REGATTA features a tropical style waterfall pool, a hot tub, a large lap pool, fitness center, gazebo bar, BBQ grills area and bay side fishing pier. Five minute drive or bicycle ride to: MERCATO upscale shops, movie-theater, restaurants and nightlife; PAVILION Shopping Center, movie-theater, restaurants, bicycle shop, LA Fitness, spa and beauty salon; PELICAN BAY Plaza Publix Supermarket, restaurants and shops. PELICAN BAY Community Park Pickleball and Tennis courts and planned programs; WIGGINS State-Park and Beach, shaded beach side BBQ grills, boat launch and fishing. Your key to Paradise is awaiting your arrival. Office Phone: (239) 261-2244 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 07/08/2025

Listed by Lesley Garlock

Days on market: 289

Property Status: Active An exclusive Regatta at Vanderbilt Beach getaway! This ninth-floor condo, situated at the end, invites abundant natural sunlight, creating a warm and inviting atmosphere. With 3 bedrooms and 2 bathrooms, the spacious open floor plan provides a comfortable and inviting space. Enjoy a spectacular view of the Gulf and Bay from the lanai, perfect for watching boats pass by and dolphins play. Under new ownership, this condo is undergoing a stylish transformation with a fresh coat of paint and all-new coastal furnishings. Immerse yourself in the soothing colors of the sky, sand, and Gulf waters, complemented by stylish accessories and fabulous light fixtures. The kitchen features updated appliances and a modern renovation, enhancing your culinary experience. This well-equipped condo is designed to fulfill all your needs for a blissful stay in paradise. Enjoy resort-style amenities, including a pool, hot tub, docks for rent, fitness rooms, and grilling areas. Tennis courts, with pickleball courts coming soon, are just up the street. Regatta's prime location on the Bay provides easy access to the beach and is within walking distance to the world-renowned Ritz Carlton, Turtle Club, and Buzz's Lighthouse. Venture to the nearby Pavilion Shops and Mercato for boutique shopping, a movie theatre, and exquisite dining options. Regatta at Vanderbilt Beach is not just a rental; it's the perfect setting to create enduring memories with family and friends. Secure your spot in paradise and make your reservation at Regatta today! Office Phone: (239) 594-2226 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 12/27/2025

Listed by Laurie Bellico, PA

Days on market: 117

Property Status: Active Life is Good at The REGATTA! One Block to Naples Pristine Beach with a Great View! Naples Florida is ranked among the Top 10 Florida vacation destinations by US NEWS & WORLD REPORT! Luxury 3BD/3BA with a spectacular panoramic water view is the perfect vacation rental for beachcombers and boaters at VANDERBILT BEACH ! Enjoy sunsets from your lanai overlooking the bay, boats, the pool and patio area. Meticulously maintained 4th fl spacious condo nicely furnished, TV'S in every room, stainless steel appliances, white kitchen cabinetry, every room has luxury vinyl flooring, painted, newer washer and dryer, oversized screen lanai, generous closet space, king, queen and 2 twin beds, covered and guest parking. The property is perfect for accommodating your guests. Sleeps 6 comfortably. THE REGATTA, a gated neighborhood situated near the GULF OF MEXICO, RITZ CARLTON and Delnor Wiggins Pass State Beach Park with a fitness center, poolside grilling, a fishing pier, social room with built-in media center, two large tropical pools and spas. Located near fine and casual restaurants, movie theaters, Whole Foods, Trader Joe's, The Capital Grille, The Mercato for boutiques, upscale dining and entertainment, The Pelican Bay PUBLIX & Marketplace. Boat Docks available. No pets, no smoking, Wi-Fi, cable & utilities included. PICK ONE 30 day stay or Rent multiple months. Available Off Season months May-October 2026 and seasonal months Nov, Dec 2026. Office Phone: (239) 529-5451 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 11/10/2025

Listed by Domenico Ceruzzi

Days on market: 164

Property Status: Active Large Gulf and Bay view overlooking the Lap pool and the marina, from the comfort of this contemporary Regatta residence; perfectly maintained 3 Bds 3 bths with tiles throughout, stainless steel appliances, stylish lights and accessories; updated guest bathrooms newly painted, WIFI controlled thermostat, keyless entry, 75" HDTV, and plentiful storage room. This residence also features under building secured parking space and additional storage. Regatta is a resort-style gated community newly built boat docks, fitness center, poolside grills, social room, tropical waterfall pool, hot tub and lap pool. Regatta's location is at perfect walking distance to Vanderbilt Beach and nearby the Ritz Carlton, Turtle Club, La Playa, and the Lighthouse restaurants Office Phone: (239) 261-2244 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 07/08/2025

Listed by Lesley Garlock

Days on market: 289

Property Status: Active This beautifully remodeled 10th-floor, 3-bedroom/3-bath condo offers over 2,000 sq ft of luxurious waterfront living with breathtaking western views of the Gulf of Mexico and the Ritz Carlton Resort. Light coastal decor, vibrant accents, and elegant wood-like porcelain tile floors create a chic and welcoming atmosphere. The spacious great room features comfortable seating, a flat-screen TV, a formal dining area, a breakfast bar, and sliding doors that lead to a screened lanai, perfect for alfresco dining with stunning views. Each bedroom includes a private en-suite bath with luxurious bedding, ensuring comfort and privacy for every guest. Regatta's top-notch amenities include a glamorous waterfall pool, waterfront lap pool, spa, gazebo, fitness center, BBQ areas, and a clubhouse. Boating enthusiasts will love the included 40ft boat slip-bring your own boat or rent one for a fun-filled vacation on the water! For beach lovers, it's just a short 700-step stroll to Vanderbilt Beach, where you can enjoy the sun, surf, water sports, and scenic beach walks. Tennis courts are conveniently located nearby at Pelican Bay Community Park. Plus, you're just minutes away from fantastic shopping, dining, and nightlife at Mercato. Explore Naples' many attractions, including Naples Botanical Gardens, Naples Zoo, Artis Naples, Celebration Park, the Naples Pickleball Center, and local farmers markets. Don't miss out on this fabulous vacation rental-book your dream getaway today! Office Phone: (239) 594-2226 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 07/08/2025

Listed by Lesley Garlock

Days on market: 289

Property Status: Active Welcome to the Regatta! This 9th floor residence offers one of the most highly sought after floor plans at Regatta with 3 bedrooms and 3 full bathrooms. With over 2000 sq ft of air conditioned space this property boasts breathtaking Gulf and Bay views from your living room, master bedroom as well as the kitchen. Enjoy modern furnishings and decor, TV's in every bedroom and is extremely well equipped making sure your stay is nothing but enjoyable. Just steps from your residence is your covered parking space, a resort style pool and lap pool, fitness room, community room, community grills and a bayside gazebo. The Regatta is perfectly situated just over a block from Vanderbilt Beach and only minutes from county tennis courts and a short drive to top rated shopping at either the Mercato, Waterside Shops and Downtown Naples. Office Phone: (239) 594-2226 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 12/02/2025

Listed by Domenico Ceruzzi

Days on market: 143

Property Status: Active Beautifully renovated 3-Beds,3-Baths 11th floor residence offering expansive northwest views of the Gulf of America and South Bay. Regatta is a gated luxury community across from the Ritz-Carlton and just a short stroll to the pristine white sands of Vanderbilt Beach and its beachfront dining. Community amenities include Tropical-style waterfall pool and hot tub, New Large lap pool, Two fitness centers, Gazebo bar and BBQ grilling areas, Bayfront fishing pier; within minutes by car or bicycle, you'll find, Mercato with its upscale shopping, dining, nightlife, and a movie theater; Pavilion Shopping Center restaurants, bars, shops, and theater; Pelican Bay Plaza: supermarket, restaurants, and retail; Pelican Bay Community Park Pickleball, Tennis, Volleyball and organized programs; Delnor-Wiggins State Park & Beach shaded picnic areas, BBQ grills, boat launch, and fishing. Relax at day's end and take in breathtaking sunsets from your private lanai. Office Phone: (239) 261-2244 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 07/08/2025

Listed by Lesley Garlock

Days on market: 289

Property Status: Active Exquisite condo at Regatta, Vanderbilt Beach, featuring stunning decor with tasteful furnishings and accessories. Meticulous attention to detail, including elegant lighting fixtures, captivating artwork, luxurious linens, and well-appointed kitchenware, makes this an ideal vacation retreat. Enjoy a comfortable and relaxing atmosphere suitable for the entire family. Revel in beautiful gulf and bay views, along with an iconic Ritz Carlton vista. The condo offers amenities like a fitness room, grills, two pools, and a marina. Walk to Vanderbilt Beach, savor sunsets at Gumbo Limbo, and dine at the Turtle Club. A short ride to Mercado offers fabulous dining, shopping, and epic nights out. Live the luxury coastal lifestyle at its finest. Office Phone: (239) 594-2226 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 07/08/2025

Listed by Lesley Garlock

Days on market: 289

Property Status: Active Stylish PENTHOUSE offers SPECTACULAR views of the GULF AND BAY. Spacious 3 bedroom and 3 bathroom condo just a short walk to the Vanderbilt Beach. Designed as a resort style community, Regatta offers amazing on-site amenities such as a fitness center, poolside grill and picnic area, furnished social room with built in media center, fishing piers, boat docks electronic gated entry, tropical waterfall pool and lap pool. Walk to nearby restaurants at the Ritz Carlton, Turtle Club, The Lighthouse and La Playa. Drive up the street to even more fine restaurants plus movie theaters, upscale shopping and more at the fabulous new Mercato, Pelican Bay Marketplace, or Pavilion Shops. Office Phone: (239) 594-2226 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 07/08/2025

Listed by Lesley Garlock

Days on market: 289

Property Status: Active Absolutely stunning, this recently renovated 3-bedroom, 3-bathroom home is a true masterpiece. Offering not only breathtaking interiors but also boasting captivating Gulf and Bay views from both the lanai and kitchen, every detail of this property has been carefully considered and impeccably executed. Step inside to discover a thoughtfully designed open floor plan adorned with beautiful furnishings and stylish accessories, creating a clean and comfortable ambiance that makes this residence an ideal choice for a perfect vacation getaway. The primary suite is a luxurious retreat featuring a lovely king-size bed and two spacious walk-in closets, ensuring a restful stay. The guest bedrooms are equally well-appointed, with comfortable accommodations including a queen bed and twin beds. The property comes complete with a range of amenities, including two pools, a spa, an exercise room, a gazebo, and two grills, providing ample opportunities for relaxation and recreation. Conveniently located within walking distance to the renowned Ritz Carlton, offering one of the best vantage points to witness Naples' breathtaking sunsets. Additionally, proximity to Vanderbilt Beach, complete with chair service and water sports, as well as shopping, dining, and vibrant nightlife at Mercado, ensures that every desire is easily fulfilled. Trade the cold embrace of snowflakes for the warmth of sunshine-this is the ultimate haven you've been searching for! Office Phone: (239) 594-2226 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Listed on 07/08/2025

Listed by Jodi Henderson

Days on market: 289

Property Status: Active Enjoy luxury living in one of the finest rental properties in the Regatta at Vanderbilt Beach! This fully renovated three-bedroom, three-bathroom, 8th-floor waterfront condominium offers a unique combination of breathtaking panoramic views of the Gulf of Mexico, the Ritz-Carlton Oceanfront Resort. The modern unit is bathed in natural light from its distinctive, unobstructed, western-facing floor plan that satisfies even the most discerning eye. It is perfect for entertaining friends and family or enjoying Naples's colorful sunsets from the private 235 square foot lanai. The unit is in the center of the Vanderbilt Beach Community, only 0.25 miles from the sandy white beach and sunshine. Regatta is designed as a resort-style community that offers excellent on-site amenities such as a newly updated fitness center, poolside grill, picnic area, electronic gated entry, tropical waterfall pool, lap pool, and hot tub. This residence features three large bedrooms and three full bathrooms, offering plenty of room for those who wish to enjoy an expansive, private stay and revel in its refined comfort. The vast master suite includes an expansive BR, flat-screen TV, walk-in closet, and 5-piece bath with double sinks, double shower head, and water closet. The living space consists of seating for 6 with views of the gulf or flatscreen TV with a Sonus surround system. The gourmet kitchen, island, and dining area are perfect for entertaining. The Regatta at Vanderbilt Beach is a premier high-rise community in Southwest Florida, with 24/7 security and gated access that offers 5-star living. Regatta is in one of the prime locations in Vanderbilt Beach, a short walk to the Ritz Carlton Oceanfront Luxury Resort and dining. It is also close to world-class shopping and dining at Mercato, Waterside Shops, and the Venetian Village, which offer a vibrant year-round atmosphere of the finest food, restaurants, and upscale retailers. Office Phone: (239) 594-2226 Copyright © 2026 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.