Search Listings

$16,000

High Rise (8+)

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…

$1,495,000

High Rise (8+)

NEWLY RENOVATED, RARELY AVAILABLE 11TH-FLOOR CONDO WITH SPECTACULAR GULF & BAY VIEWS in the highly sought-after Regatta community on Vanderbilt Beach! Ideally located directly across from the Naples Ritz-Carlton Beach Resort and just a 10-minute…

$13,500

High Rise (8+)

Experience coastal living at its finest in this beautifully furnished and updated 3-bedroom, 2-bath condo in the sought-after Regatta community. Ideally located just a short walk from Vanderbilt Beach, this residence places you near some…

$15,000

High Rise (8+)

LUXURY BAYSIDE SEASONAL RENTAL… AVAILABLE JANUARY & APRIL 2027 AND JUNE THROUGH DECEMBER 2026 - Beautifully refreshed 3BR/3BA residence in Regatta at Vanderbilt Beach, located in highly desirable Building One and offering one of the…

$2,650,000

High Rise (8+)

Where contemporary elegance meets the effortless beauty of Florida’s Gulf Coast, this completely reimagined residence offers a lifestyle defined by sophisticated comfort and coastal ease. From the moment you enter, you're welcomed into an atmosphere…

$3,000

Mid Rise (4-7)

This top floor condo is located just a couple of minutes walk to the beach. This is a 3BR/2BA with a West Indies decor. Regatta offers amazing on-site amenities such as fitness center, poolside grill…

$14,500

High Rise (8+)

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…

$14,000

High Rise (8+)

Located on Vanderbilt Bay 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…

$13,500

High Rise (8+)

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…

$11,500

High Rise (8+)

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…

$3,500

Mid Rise (4-7)

Your week-long escape begins in this 3BR/2BA end unit at Regatta! Enjoy cozy furnishings, stylish accessories, and a well-equipped kitchen. A mere short walk will lead you to the tranquil shores of the Gulf of…

$3,000

Mid Rise (4-7)

This impeccably maintained 3BR/2BA condo, with its island-style décor and sunny western exposure, invites you to unwind in comfort. It comes fully furnished with a well-equipped kitchen, luxurious linens, and everything you need for a…

$3,000

Mid Rise (4-7)

This bright and cheerful Regatta condo is perfectly poised for enjoying serene lanai sunsets while overlooking the resort-style pool or taking a short stroll to the beach. Spacious floor plan with updated kitchen including stainless…

$3,000

Mid Rise (4-7)

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…

$4,000

Mid Rise (4-7)

Located on Vanderbilt Bay this lovely 4th floor condo just 500 steps to the beach appears surreal as its charm and elegance inspire you for costal life-on-the-bay! Splashed in the vivid palette of calming colors,…

$14,000

Mid Rise (4-7)

Just steps from Vanderbilt Beach! This beautiful 3BR/2BA condo is a short walk to the white sandy shores, perfect for relaxing, enjoying stunning sunsets, or trying out water sports. Recently updated with new furnishings and…

$15,400

High Rise (8+)

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…

$16,000

High Rise (8+)

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…

$15,000

High Rise (8+)

WEEKLY RATES AVAILABLE - Beautifully furnished 3 BR/3BA CONDO located on the 11th floor of the Regatta with Spectacular views of Vanderbilt Bay, the Gulf of Mexico, and Sanibel Island to the North from the…

$14,000

Mid Rise (4-7)

Where luxury meets effortless coastal living. This beautifully updated residence offers approximately 1,700 square feet of open, light-filled living space with a thoughtfully designed 3-bedroom, 2-bath layout—perfect for relaxing and entertaining. Natural light enhances the inviting…

$7,000

High Rise (8+)

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…

$1,050,000

Mid Rise (4-7)

Experience the best of Naples coastal living in this beautifully updated 5th-floor condo at 470 Launch Cir #V-503, located in the highly desirable Regatta community just steps from Vanderbilt Beach. Featuring one of the most…

$1,695,000

High Rise (8+)

This spacious end unit has been renovated and furnished to perfection, featuring high-end finishes and beautiful furniture that complement the incredible bay views from your large lanai. With a separate living floor plan, the primary…

$14,000

High Rise (8+)

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…

$8,500

High Rise (8+)

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…

$1,495,000

High Rise (8+)

Experience stunning Vanderbilt Bay and marina views from the oversized lanai of this highly coveted largest floor plan in the Regatta community, offering 2,320 sq. ft. of living space. This spacious residence features 3 bedrooms,…

$15,000

High Rise (8+)

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…

$14,000

Mid Rise (4-7)

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…

$1,150,000

Mid Rise (4-7)

Directly across the Naples Ritz Carlton Beach resort! Ready to move in to warm, sunny Naples with min 250 days of sunshine and ranked as one of the happiest and healthiest communities. How many people…

$18,000

High Rise (8+)

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,…

$14,000

High Rise (8+)

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…

$1,395,000

High Rise (8+)

Experience true coastal elegance on the bay in this luxurious 5th-floor corner residence, where stunning panoramic bay views greet you the moment you walk through the door. Bathed in natural light from windows on three…

$1,400,000

High Rise (8+)

Coastal Charm by the Gulf – This bright 9th-floor end-unit condo brings nearly 2,000 sq. ft. of relaxed, open living with stunning Gulf and Bay views. With three bedrooms and two-and-a-half baths, the airy layout…

$15,000

High Rise (8+)

Enjoy the best of coastal Naples at this beautifully located residence in Regatta at Vanderbilt Beach. With peaceful bay views, a private patio, and just a five-minute walk to the beach, this property offers the…

$12,000

High Rise (8+)

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 --…

$14,000

Mid Rise (4-7)

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…

$12,000

High Rise (8+)

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…

$15,000

High Rise (8+)

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…

$10,000

High Rise (8+)

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…

$14,500

High Rise (8+)

Escape to paradise in this stunning 3 bedroom, 3 bathroom terrace condo with breathtaking bay views and over 600 sq. ft. of private outdoor living space—perfect for sunset cocktails, family dinners, or simply unwinding in…

$4,000

High Rise (8+)

Nestled along Vanderbilt Beach, this stunning resort-style community is just a short stroll from sandy white shores and breathtaking, colorful sunsets. Regatta boasts exceptional on-site amenities, including a weight and cardio room, poolside grill and…

$15,000

High Rise (8+)

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.…

$14,000

High Rise (8+)

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 décor, vibrant accents, and…

$16,000

High Rise (8+)

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…

$3,000

Mid Rise (4-7)

Embark on a week-long escape to the dazzling paradise of Regatta - where every moment is bathed in sunlight and pure bliss! This immaculate 3BR/2BA end unit is a spacious retreat, boasting stylish furnishings and…

$3,000

Mid Rise (4-7)

$3000/week - $12,000/month. Looking for the perfect coastal getaway? This stunning 3BR/2BA condo is just what you need! Overlooking the beautiful bay, you can watch boats sail by and dolphins play from the comfort…

$1,099,000

Mid Rise (4-7)

Welcome to Regatta—Where Every Day Begins and Ends with a View! Wake up to vibrant sunrises and wind down with stunning sunsets, all from the comfort of your home. This condo stands out as one…

$1,400,000

High Rise (8+)

Welcome to this beautifully remodeled waterfront condominium, just a short walk to the pristine sands of Vanderbilt Beach! Enjoy living in one of Naples’ most desirable locations, across from The Ritz Carleton with easy access…

$1,395,000

High Rise (8+)

Come See One of the BEST Values Along Vanderbilt Beach! This 8th-floor condo with breathtaking Gulf and Bay views won’t last long! Imagine watching boats pass by and dolphins play from your beautiful outdoor living…

$1,400,000

High Rise (8+)

This exceptional terrace condo presents highly sought-after, breathtaking bay views that can be enjoyed from the expansive private terrace—spanning over 600 square feet of outdoor space perfect for entertaining, dining, and family gatherings. Convenient staircases…

$1,599,000

High Rise (8+)

Rare Opportunity to own the largest Floor Plan in the most sought after stack at Regatta 1. This 3 Beds -3Baths residence offers a generous size master suite with french doors to access the lanai…

$1,699,000

High Rise (8+)

Immerse yourself in the ultimate luxury living experience at Regatta with this exceptional penthouse, showcasing breathtaking coastal views. Situated on the top floor with no neighbors above or hallway windows, this meticulously upgraded residence…

$1,150,000

Mid Rise (4-7)

COMPARE TO ANYTHING ON THE MARKET!! Naples was just voted the NUMBER ONE PLACE TO LIVE IN FLORIDA!! Couple that with an amazing PET FRIENDLY (no size limitations!) 3-bedroom opportunity to: walk a couple…