Listed on 05/18/2026

Listed by Matt Lane

Days on market: 122

Property Status: Active The Ultimate Naples Waterfront Lifestyle - Private Garage, Expansive Terrace & Boat Dock - Everything You Want in a Naples Residence. Rarely available as an annual rental at Regatta, this spacious, beautifully updated waterfront condo offers an exceptional coastal living experience. The standout feature is the expansive 400+ sq. ft. open-air terrace-an incredibly rare find in condominium living-perfect for entertaining, relaxing, or taking in sweeping views of Vanderbilt Bay and stunning sunsets. The terrace has been upgraded with new brick pavers and includes a private staircase with direct access to the pool area. Inside, this 3-bedroom + den, 2.5-bath residence features an open, airy layout with elegant wood flooring throughout the main living areas and a thoughtfully renovated interior designed for both comfort and style. The eat-in kitchen is equipped with stainless steel appliances, an induction range, granite countertops, and classic shaker cabinetry, complemented by designer finishes that add character and warmth. Offered beautifully furnished in a light, coastal style, the home is completely turnkey for an effortless annual stay. Additional highlights include a highly desirable oversized 1.5-car private garage, providing ample room for parking and storage. Boating enthusiasts will appreciate the availability of a 40' boat slip with lift, making it easy to enjoy life on the water. Residents of Regatta enjoy a gated, well-maintained community with resort-style amenities, including two pools (one featuring a tranquil waterfall), fitness rooms, grilling areas, and a clubhouse. Ideally located just a short walk to Vanderbilt Beach and nearby restaurants, with convenient access to Mercato, Waterside Shops, and more. This is a rare opportunity to enjoy space, views, and location in one of Naples' most desirable waterfront communities. 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 05/17/2026

Listed by Matt Lane

Days on market: 123

Property Status: Active Discover the ultimate vacation retreat in this 3BR+open den/2.5BA condo at Regatta at Vanderbilt Beach. This spacious 11th-floor end unit, adorned with tropical island-style decor, boasts stunning gulf and bay views across a generous 2,000-square-foot open living space. The expansive lanai is the perfect spot to unwind and take in breathtaking sunsets after a day at the beach. Fully furnished and equipped, this condo offers everything you need for a tranquil stay in paradise. Just a short walk from Vanderbilt Beach, Regatta provides a resort-style experience with amenities including a fitness center, poolside grill, picnic area, gated entry, tropical waterfall pool, lap pool, and more. Tennis and pickleball courts will soon be available at the nearby community park. Enjoy local dining favorites like the Ritz Carlton, Turtle Club, The Lighthouse, and La Playa, or venture out for fine dining, entertainment, and shopping at Mercato, Pelican Bay Marketplace, or Pavilion Shops. Naples offers a wealth of attractions, from fishing and sunset cruises to the Naples Botanical Gardens, Naples Zoo, public golf courses, and the cultural hub of Artis Naples. Embrace the Southwest Florida lifestyle at Regatta-there's no better place to experience the good life! This property is not available for an annual lease. 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 05/18/2026

Listed by David Roy, PA

Days on market: 122

Property Status: Active Welcome to this stunning 11th-floor condo at The Regatta, offering breathtaking, panoramic views of Vanderbilt Bay, the Gulf of Mexico, and Sanibel Island from your private screened lanai. Beautifully furnished and meticulously maintained, this 3-bedroom, 3-bathroom condo features a bright, open-concept layout that seamlessly connects the living, dining, and kitchen areas. Located in a secure, gated community right across from the Ritz-Carlton, you're just a short, scenic stroll from the pristine white sands of Vanderbilt Beach. The Regatta offers incredible resort-style amenities, including a gorgeous tropical lagoon pool with a waterfall, a lap pool overlooking the bay, a fully equipped fitness center, a hot tub, and a clubhouse with barbecue grills. Inside, the condo is finished with elegant crown molding, privacy shades, hurricane shutters, and a mix of warm wood and tile flooring throughout. The primary suite is a comfortable retreat with a king bed and beautiful custom closets, while the two guest bedrooms (one with a queen bed and the other with twins) offer plenty of space for family or visitors. This home is completely turnkey and ready for you, equipped with high-speed internet, cable, four TVs, and a landline. A unique bonus for this unit is its own enclosed garage space and additional parking in front of the building. When you're ready to explore, you are within walking distance of Vanderbilt Beach, the Ritz-Carlton, the La Playa Hotel, and the fantastic shopping, dining, and nightlife at Mercato. Weekly rates are also available. 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 05/18/2026

Listed by Matt Lane

Days on market: 122

Property Status: Active Experience paradise at Regatta in this bright and sunny 8th-floor end unit offering 3 bedrooms, 2.5 baths, plus a cozy den - providing plenty of space to relax, unwind, and enjoy the Naples lifestyle. Beautifully decorated with tropical-inspired furnishings, this updated residence features all new bedding, luxurious linens, and thoughtfully stocked kitchen essentials to ensure a comfortable and effortless stay. The fully equipped kitchen has everything you need for preparing meals at home, while the spacious living areas create the perfect setting for gathering with family and friends. Step out onto the expansive lanai and enjoy breathtaking Gulf and bay views - the perfect place to relax with morning coffee or take in Naples' spectacular sunsets each evening. Regatta's outstanding resort-style amenities include a tropical pool, hot tub, fitness center, BBQ grilling area, and beautifully maintained grounds, offering endless opportunities for relaxation and fun. Best of all, you are just a short walk to the beach where you can spend your days soaking up the sun, swimming in the Gulf, shelling, or enjoying a variety of water activities. Ideally located near some of Naples' most popular dining destinations including the Ritz-Carlton, Turtle Club, The Lighthouse, and LaPlaya. Additional shopping, dining, and entertainment options are just minutes away at Mercato, Pelican Bay Marketplace, and Pavilion Shops. Your perfect Naples vacation awaits at Regatta! 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 05/18/2026

Listed by Matt Lane

Days on market: 122

Property Status: Active Escape to paradise at Regatta, an exceptional vacation rental designed for comfort, style, and effortless coastal living. This spacious 3-bedroom, 3-bath residence offers an inviting retreat with plenty of room to relax in a serene waterfront setting. Unwind on the extended outdoor living space, where breathtaking sunsets paint the sky each evening. Watch dolphins glide through the bay and boats pass by, creating a peaceful, ever-changing backdrop. Inside, the residence features a light, coastal-inspired design with comfortable furnishings, a fully equipped and updated kitchen, and high-quality linens and towels-everything you need for a seamless stay. Guests enjoy access to Regatta's outstanding resort-style amenities, including a tropical pool, lap pool, hot tub, fitness center, and BBQ areas-perfect for both relaxation and recreation. The beach is just a short stroll away, offering easy access to sun, sand, and Gulf waters. Ideally located near some of Naples' most sought-after dining spots, including the Ritz-Carlton, Turtle Club, The Lighthouse, and LaPlaya, with additional shopping, dining, and entertainment just minutes away at Mercato, Pelican Bay Marketplace, and Pavilion Shops. Public tennis and pickleball courts are also nearby. Your perfect Naples getaway starts here. Weekly reservations between January 1 and April 30 require a Saturday-to-Saturday stay. For dates outside of this timeframe, please inquire. 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 05/17/2026

Listed by Matt Lane

Days on market: 123

Property Status: Active Welcome to Glamour by the Gulf, a luxury waterfront residence in the highly sought-after Regatta at Vanderbilt Beach where refined coastal style meets effortless comfort. Offering the community's largest floor plan with over 2,300 square feet, this spacious residence features 3 beautifully appointed bedrooms and 3.5 baths, thoughtfully designed for both privacy and relaxation. From the moment you enter through the grand double doors, you're greeted by a light-filled, open-concept layout ideal for entertaining and unwinding. Designer furnishings, curated lighting, and sophisticated coastal decor create a serene yet glamorous atmosphere, while expansive windows showcase stunning bay and Gulf views. The chef-inspired kitchen is both elegant and functional, complete with custom cabinetry, expansive granite countertops, premium appliances, and a dedicated coffee bar for leisurely mornings. The dining and living areas flow seamlessly together, creating inviting spaces to gather, celebrate, or simply relax after a day at the beach. Each bedroom serves as a private retreat, offering generous space and spa-like en-suite baths. Every bed is draped in luxury hotel-quality linens, ensuring a restful night's sleep, while each bathroom is stocked with plush, soft towels for a true resort-style experience. The primary suite delivers added comfort and tranquility, perfect for extended stays or special getaways. Step outside to the furnished lanai, your personal sunset lounge, where you can sip cocktails, watch boats cruise by, and spot dolphins playing in the bay. For boating enthusiasts, Regatta offers direct Gulf access through Delnor-Wiggins Pass State Park, with the option to rent a private 24-foot slip with lift. With secure gated entry, covered parking, extra storage for beach gear and toys, and just steps from the white sands of Vanderbilt Beach, plus dining and resort experiences at The Ritz-Carlton Naples, everything you need for a five-star stay is at your fingertips. Glamour by the Gulf isn't just a vacation rental - it's a luxury escape designed for comfort, coastal elegance, and unforgettable memories. This property is not available for an annual lease. 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.