$12,000 per month
- 2 Beds
- 2 Baths
- 1,145 Sq Ft
- Condo for Rent
9415 Gulf Shore Dr Unit 302, Naples, FL 34108
9415 Gulf Shore Dr Unit 302, Naples, FL 34108
238
Vanderbilt Beach Homes for Rent
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$11,500 per month
- 5 Beds
- 6.5 Baths
- 4,420 Sq Ft
- House for Rent
405 Trade Winds Ave, Naples, FL 34108
405 Trade Winds Ave, Naples, FL 34108 -
$8,000 per month
- 1 Bed
- 1 Bath
- 1,045 Sq Ft
- Condo for Rent
10420 Gulf Shore Dr Unit 162, Naples, FL 34108
10420 Gulf Shore Dr Unit 162, Naples, FL 34108 -
$2,990 per month
- 1 Bed
- 1 Bath
- 581 Sq Ft
- Condo for Rent
260 Southbay Dr Unit ID1226371P, Naples, FL 34108
260 Southbay Dr Unit ID1226371P, Naples, FL 34108Indulge in the ultimate coastal living experience with this stunning one-bedroom condo, ideally located just off Vanderbilt Beach Road in North Naples. Situated on the second floor, this unit offers easy access with an elevator and self check-in convenience. Revel in the convenience of having a plethora of exceptional restaurants, including the renowned Gumbo Limbo at The Ritz, within walking
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$30,000 per month
- 4 Beds
- 3 Baths
- 3,034 Sq Ft
- House for Rent
159 Conners Ave, Naples, FL 34108
159 Conners Ave, Naples, FL 34108Available for 2026 Season or off season from May 7 through the end of November. This one of a kind 4BR/3BA turnkey furnished single-family pool/spa home in the Conners off Vanderbilt is truly a hidden gem. Comes with its own boat dock and a location that is hard to beat. This unique coastal home is professionally decorated, where modern design and luxury awaits you. The well-equipped gourmet
Stephanie Spooner WeichertRealtors-ParadiseHomes
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$2,890 per month
- 1 Bed
- 1 Bath
- 904 Sq Ft
- Condo for Rent
260 Southbay Dr Unit ID1226374P, Naples, FL 34108
260 Southbay Dr Unit ID1226374P, Naples, FL 34108Indulge in the ultimate coastal living experience with this stunning one-bedroom condo, ideally located just off Vanderbilt Beach Road in North Naples. This unit is on the second floor and offers self check-in. Revel in the convenience of having a plethora of exceptional restaurants, including the renowned Gumbo Limbo at The Ritz, within walking distance. Moreover, you're only a two-minute stroll
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$9,000 per month
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
- Condo for Rent
9380 Gulf Shore Dr Unit 102, Naples, FL 34108
9380 Gulf Shore Dr Unit 102, Naples, FL 34108Discover the perfect vacation rental nestled by the bay with front door views of the Gulf of America. This spacious 3-bedroom, 2-bathroom condo with a screened lanai offers the ultimate retreat. Enjoy private beach access right across the street, featuring stunning water views. Inside, you'll find large bedrooms and the convenience of in-unit laundry. The property includes underground parking
Tina Keppy William Raveis Real Estate
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$7,000 per month
- 2 Beds
- 2 Baths
- 1,177 Sq Ft
- Condo for Rent
10686 Gulf Shore Dr Unit 304, Naples, FL 34108
10686 Gulf Shore Dr Unit 304, Naples, FL 34108This highly sought after third floor two bedroom, two bathroom unit in Monte Carlo Club on Vanderbilt Beach is the perfect winter retreat for those who are looking for comfort, charm, stunning views and a property that is so well equipped you will feel like you haven't left home. Freshly painted, new luxury vinyl flooring in living area, and updated bathrooms. Featuring a Tommy Bahama style
Christine Yeaw Phase III Real Estate Services
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$13,000 per month
- 3 Beds
- 3 Baths
- 1,750 Sq Ft
- Condo for Rent
400 Flagship Dr Unit 407, Naples, FL 34108
400 Flagship Dr Unit 407, Naples, FL 34108Seasonal Rental – Steps from Vanderbilt Beach!Welcome to this stunning 3-bedroom, 2-bathroom corner unit in the prestigious Regatta at Vanderbilt Beach. Located just a short walk to the sand and the Ritz-Carlton, this spacious residence features elegant marble flooring throughout and an expansive wrap-around balcony with breathtaking bay views—perfect for enjoying Naples’ famous
Ewa Fila Downing Frye Realty Inc.
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$7,500 per month
- 2 Beds
- 2 Baths
- 1,248 Sq Ft
- Condo for Rent
10684 Gulf Shore Dr Unit 305, Naples, FL 34108
10684 Gulf Shore Dr Unit 305, Naples, FL 34108Fantastic location!!! See sunrise and sunsets from this 2 bedroom + Den 2 bath condo. Monte Carlo is a gated community located directly across the street from Vanderbilt Beach and close to Wiggins State Park. There is assigned covered parking with additional guest parking available, large heated community pool, tennis and a common elevator for easy access to the unit. Location is
Grace Meholick Premier Sotheby's Int'l Realty
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$20,000 per month
- 3 Beds
- 3.5 Baths
- 2,320 Sq Ft
- Condo for Rent
410 Flagship Dr Unit 1104, Naples, FL 34108
410 Flagship Dr Unit 1104, Naples, FL 34108Enjoy coastal elegance in this luxuriously appointed 3-bedroom, 3.5-bath residence on the 11th floor of the Regatta. This bayfront property features two ensuites, a wet bar with wine/beverage cooler, and a large, screened Lanai for sunrise breakfast or sunset dining. Offering breathtaking Gulf views, this property is a short walk from Vanderbilt Beach and across from the Ritz Carlton; Regatta
Domenico Ceruzzi Downing Frye Realty Inc.
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$10,000 per month
- 1 Bed
- 1 Bath
- 600 Sq Ft
- Condo for Rent
260 Southbay Dr Unit 204, Naples, FL 34108
260 Southbay Dr Unit 204, Naples, FL 34108Available Now – December 2025 and 2026 Season | Weekly or Monthly Rentals!Call for current availability and rate specials – also listed on multiple booking platforms.Welcome to Vanderbilt Palms, your coastal oasis just 500 feet from the Gulf of Mexico! This spacious and fully furnished 1-bedroom, 1-bath condo offers flexible weekly or monthly rental options—with no association approval
Christina Falzarano Bajrakta The Real Estate Connection LLC
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$17,000 per month
- 2 Beds
- 2 Baths
- 1,560 Sq Ft
- Condo for Rent
10701 Gulf Shore Dr Unit 1002, Naples, FL 34108
10701 Gulf Shore Dr Unit 1002, Naples, FL 34108Available March 2026! Experience the ultimate in coastal luxury with this stunning 10th-floor beachfront condo at The Seville, located in the prestigious Vanderbilt Shores high-rise in Naples. Rarely available, this beautifully situated residence showcases panoramic, west-facing views of the Gulf of Mexico from an expansive private balcony, perfect for soaking in breathtaking sunsets every
Robert Nardi WeichertRealtors-ParadiseHomes
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$16,000 per month
- 3 Beds
- 2 Baths
- 1,546 Sq Ft
- Condo for Rent
9700 Gulf Shore Dr Unit 202, Naples, FL 34108
9700 Gulf Shore Dr Unit 202, Naples, FL 34108La Scala – Vanderbilt Beach2 Bed | 2 Bath | Breathtaking Bay & Gulf ViewsExperience the best of Vanderbilt Beach in this beautifully updated residence at La Scala, where every day begins with unobstructed sunrisesover the Bay and ends with spectacular Gulf sunsets just outside your front door.This coastal retreat features new floors, a brand-new kitchen, and impact-rated windows
Joe Hoopfer Premier Sotheby's Int'l Realty
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$15,300 per month
- 2 Beds
- 2 Baths
- 1,489 Sq Ft
- Condo for Rent
Unlisted Address
Unlisted AddressBEACH, BEACH, AND MORE BEACH! Experience the charm of this delightful 2BR/2BA condo, adorned with classic furnishings and offering all the comforts of home. There's no better way to spend your vacation than at Vanderbilt Gulfside ON THE BEACH. Witness breathtaking sunrises and mesmerizing sunsets! Nestled on 8 acres of lush tropical landscape, this paradise boasts a magnificent 40x60 heated
Lesley Garlock William Raveis Real Estate
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$4,000 per month
- 3 Beds
- 3 Baths
- 1,860 Sq Ft
- Condo for Rent
410 Flagship Dr Unit 505, Naples, FL 34108
410 Flagship Dr Unit 505, Naples, FL 34108Nestled 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 picnic area, electronic gated entry, hot tub, tropical waterfall pool, and lounge pool. This spacious and updated 3BR/3BA condo features an open
Lesley Garlock William Raveis Real Estate
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$3,000 per month
- 3 Beds
- 2 Baths
- 1,635 Sq Ft
- Condo for Rent
460 Launch Cir Unit 401, Naples, FL 34108
460 Launch Cir Unit 401, Naples, FL 34108Embark 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 accessories that add a touch of sophistication to your vacation. Fully equipped to ensure your stay is nothing short of delightful, the open floor plan is perfect for family gatherings.
Lesley Garlock William Raveis Real Estate
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$3,000 per month
- 3 Beds
- 2 Baths
- 1,475 Sq Ft
- Condo for Rent
450 Launch Cir Unit 203, Naples, FL 34108
450 Launch Cir Unit 203, Naples, FL 34108Looking 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 of your private lanai. Ideal for families and friends, the spacious condo features a cozy living room for relaxing together, a fully equipped kitchen for all your cooking adventures, and is comfortably furnished
Lesley Garlock William Raveis Real Estate
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$16,000 per month
- 3 Beds
- 3 Baths
- 1,765 Sq Ft
- Condo for Rent
400 Flagship Dr Unit 602, Naples, FL 34108
400 Flagship Dr Unit 602, Naples, FL 34108Absolutely 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
Lesley Garlock William Raveis Real Estate
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$15,000 per month
- 3 Beds
- 3 Baths
- 2,035 Sq Ft
- Condo for Rent
400 Flagship Dr Unit 1207, Naples, FL 34108
400 Flagship Dr Unit 1207, Naples, FL 34108Stylish 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
Lesley Garlock William Raveis Real Estate
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$15,000 per month
- 3 Beds
- 3 Baths
- 1,750 Sq Ft
- Condo for Rent
400 Flagship Dr Unit 705, Naples, FL 34108
400 Flagship Dr Unit 705, Naples, FL 34108Exquisite 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
Lesley Garlock William Raveis Real Estate
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$14,000 per month
- 3 Beds
- 3 Baths
- 2,035 Sq Ft
- Condo for Rent
400 Flagship Dr Unit 1002, Naples, FL 34108
400 Flagship Dr Unit 1002, Naples, FL 34108This 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
Lesley Garlock William Raveis Real Estate
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$14,000 per month
- 2 Beds
- 2 Baths
- 1,227 Sq Ft
- Condo for Rent
10562 Gulf Shore Dr Unit 202, Naples, FL 34108
10562 Gulf Shore Dr Unit 202, Naples, FL 34108A beautifully renovated condo nestled by the bay, exuding coastal elegance. The inviting interiors feature comfortable furnishings, stylish accents, and vibrant hues, creating a tropical oasis. This end unit offers breathtaking views of the Gulf of Mexico to the west and the serene bay to the east. Completely redone, it includes a well-equipped kitchen with all essentials for your stay. Each
Lesley Garlock William Raveis Real Estate
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$21,500 per month
- 3 Beds
- 3.5 Baths
- 3,252 Sq Ft
- Condo for Rent
10620 Gulf Shore Dr Unit 602, Naples, FL 34108
10620 Gulf Shore Dr Unit 602, Naples, FL 34108Exceptional 3 bedroom plus den, 3 and a half bath residence width over 3,000 Sq. Ft. under air and 10' ceilings. This private residence is one of 15 in the building with private elevator service includes a 2 car garage and boat dock (3) . Enjoy the evening sunsets from the expansive balcony overlooking the Bay and of the Gulf. The Bellagio Grand is a gated community featuring a pool, spa,
Joe Hoopfer Premier Sotheby's Int'l Realty
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$8,500 per month
- 2 Beds
- 2 Baths
- 1,056 Sq Ft
- Condo for Rent
271 Southbay Dr Unit 152, Naples, FL 34108
271 Southbay Dr Unit 152, Naples, FL 34108Welcome to your slice of paradise at Barefoot Pelican #152! This top floor 2-bedroom, 2-bathroom condo offers breathtaking bay views and a coastal contemporary design that's both stylish and comfortable. With tile flooring throughout, granite countertops, and stainless steel appliances, the interior exudes modern elegance. The renovated master shower add a touch of luxury to your daily routine.
Cindy Rosenfeld Premiere Plus Realty Company
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$11,500 per month
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
- Condo for Rent
10682 Gulf Shore Dr Unit 301, Naples, FL 34108
10682 Gulf Shore Dr Unit 301, Naples, FL 34108Welcome to the PREMIER SEASONAL RENTAL on VANDERBILT BEACH! Experience coastal living at its finest in this beautifully remodeled 3 bedroom, 2-bath Bayfront condo, within the gated community of Monte Carlo Club. Just steps from the sugar sand beaches of Vanderbilt Beach, every inch of this stunning residence has been thoughtfully upgraded. Your future home away from home boasts an open
Claudia DeJesus Palm Paradise Realty Group
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$16,000 per month
- 3 Beds
- 2.5 Baths
- 1,979 Sq Ft
- Condo for Rent
Unlisted Address
Unlisted AddressPLEASE ASK ABOUT WEEKLY RATES: Welcome to your dream escape in one of Naples’ most iconic vacation destinations—Vanderbilt Beach. This rarely available Regatta penthouse offers breathtaking panoramic views, capturing both vibrant sunrises and unforgettable sunsets. With 3 bedrooms, 2.5 baths, and an open den, this spacious end-unit residence ensures privacy, tranquility, and comfort. No neighbors
Lesley Garlock William Raveis Real Estate
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$16,000 per month
- 3 Beds
- 3 Baths
- 2,003 Sq Ft
- Condo for Rent
10851 Gulf Shore Dr Unit 1001, Naples, FL 34108
10851 Gulf Shore Dr Unit 1001, Naples, FL 34108Wonderful Three Bedroom, Three Bathroom 10th floor end unit. This unit has been renovated and boasts wonderful furnishings with a relaxed beach cottage flair! Master Bedroom features a king sized bed and television, guest bedroom features a queen sized bed and television, 2nd guest bedroom features two twin beds. You will enjoy incredible Bay and Gulf views from sunrise to sunset as well as
Christine Yeaw Phase III Real Estate Services
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$18,000 per month
- 2 Beds
- 2 Baths
- 1,600 Sq Ft
- Condo for Rent
10851 Gulf Shore Dr Unit 303, Naples, FL 34108
10851 Gulf Shore Dr Unit 303, Naples, FL 34108Stunning Beachfront Retreat with Dual Master Suites – Vanderbilt Gulfside, Naples FLExperience the ultimate in coastal luxury at this beautifully renovated 2-bedroom, 2-bath condominium located on the 3rd floor of the exclusive Vanderbilt Gulfside community in Naples, Florida. Designed for comfort and style, this spacious residence features two private master suites, perfect for couples or guests
Christine Yeaw Phase III Real Estate Services
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$5,600 per month
- 2 Beds
- 2 Baths
- 1,490 Sq Ft
- Condo for Rent
10682 Gulf Shore Dr Unit 304, Naples, FL 34108
10682 Gulf Shore Dr Unit 304, Naples, FL 34108Wonderful Two Bedroom, Two Bathroom 3rd floor unit with incredible bay views! Vaulted ceilings, private balcony this unit has been maintained to perfection! Queen size bed in the master bedroom, two twins in the guest. This unit offers all of the comforts of home with wi-fi internet and flat screen televisions! A boat dock is available with the rental of this unit. Steps to the community pool and
Christine Yeaw Phase III Real Estate Services
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$17,000 per month
- 3 Beds
- 3 Baths
- 2,003 Sq Ft
- Condo for Rent
10851 Gulf Shore Dr Unit 605, Naples, FL 34108
10851 Gulf Shore Dr Unit 605, Naples, FL 34108A dream beach vacation becomes reality in this Key West styled three bedroom/three bathroom condominium. The southwest exposure of this corner unit fills the living, dining and kitchen areas with abundant natural light and the Gulf breeze. The kitchen offers abundant space for meal preparation and a beautiful vista. The living and dining areas lead to the main lanai and wrap around balcony
Christine Yeaw Phase III Real Estate Services
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$7,000 per month
- 3 Beds
- 2 Baths
- 1,639 Sq Ft
- Condo for Rent
470 Launch Cir Unit 405, Naples, FL 34108
470 Launch Cir Unit 405, Naples, FL 34108Just 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 accessories, it offers a fresh and stylish retreat. Located in the resort-style community of Regatta, you’ll have access to fantastic amenities like a fitness center,
Tony Blaskis William Raveis Real Estate
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$14,500 per month
- 3 Beds
- 3 Baths
- 2,035 Sq Ft
- Condo for Rent
400 Flagship Dr Unit 302, Naples, FL 34108
400 Flagship Dr Unit 302, Naples, FL 34108AVAILABLE FOR SEASON 2026! MULTIPLE MONTHS PREFERRED JANUARY THROUGH APRIL. ALSO AVAILABLE BI-WEEKLY MAY THROUGH DECEMBER 2025. CONDO HAS BEEN FRESHLY PAINTED, BATHROOMS JUST RENOVATED AND MORE! UPDATED KITCHEN with Granite and Stainless Appliances! The LARGEST and most open floor plan in building ONE, this tastefully decorated 3 bedroom 3 bath condo is bright and crisp with over sized tile
Louise Messina Phase III Real Estate Services
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$12,000 per month
- 3 Beds
- 2 Baths
- 1,475 Sq Ft
- Condo for Rent
470 Launch Cir Unit 503, Naples, FL 34108
470 Launch Cir Unit 503, Naples, FL 34108AVAILABLE FOR SEASON 2026. WEEKLY/BI-WEEKLY MAY THROUGH DECEMBER 2025. RENOVATED BATHROOMS AND KITCHEN WITH GRANITE AND STAINLESS APPLIANCES ~ FABULOUS LOCATION~ MOST DESIRED FLOOR PLAN in Building 5 with an OVERSIZED TILED LANAI. Lovely 5th Floor Condo is decorated in warm, neutral tones and upgraded with Tile Floors throughout to include CUSTOM WOOD LOOK TILE FLOORING in the Living Room &
Louise Messina Phase III Real Estate Services
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$8,000 per month
- 2 Beds
- 2 Baths
- 1,075 Sq Ft
- Condo for Rent
271 Southbay Dr Unit 235, Naples, FL 34108
271 Southbay Dr Unit 235, Naples, FL 34108AVAILABLE FOR SEASON 2026 AND OFF SEASON 2025! 3 MONTHS PREFERRED. Bi-Weekly Rentals Available Off Season through December. LESS THAN 1 BLOCK WALK TO VANDERBILT BEACH! Beautifully Renovated 2-bedroom, 2-bath condominium on the bay is crisp and bright, designed with straight lines and tastefully decorated with a beachy yet contemporary flare! TILE FLOORS THROUGHOUT… The kitchen and both bathrooms
Louise Messina Phase III Real Estate Services
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$10,500 per month
- 4 Beds
- 3 Baths
- 2,913 Sq Ft
- House for Rent
291 Heron Ave, Naples, FL 34108
291 Heron Ave, Naples, FL 34108Live the Naples lifestyle in this fully updated 4-bedroom, 3 full baths, canal front home in the popular Conners at Vanderbilt Beach! This stylish home offers modern upgrades, a bright open layout, and a private pool. The entire home has been designed with comfort and style in mind.Boaters will love the direct canal access—you’ll be in the Gulf of Mexico in just minutes. And when you’re not on
Alfredo Camacho Landmark Living Solutions, LLC.
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$12,000 per month
- 2 Beds
- 2 Baths
- 1,472 Sq Ft
- Condo for Rent
11030 Gulf Shore Dr Unit 901, Naples, FL 34108
11030 Gulf Shore Dr Unit 901, Naples, FL 34108This beautifully renovated 2-bedroom, 2-bath condo on the 9th floor offers sweeping views of the bay and Gulf from one of North Naples' most desirable locations, just steps from the beach. Whether you're seeking a seasonal retreat or a longer stay, this fully furnished residence combines coastal charm with modern luxury. The open-concept living space is flooded with natural light and features a
Tracy Guillot Realty One Group MVP
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$8,000 per month
- 3 Beds
- 3 Baths
- 1,475 Sq Ft
- Apartment for Rent
9524 Gulf Shore Dr Unit 2, Naples, FL 34108
9524 Gulf Shore Dr Unit 2, Naples, FL 34108Don't Delay, Your Beach Chair Awaits! Vanderbilt Beach bayfront triplex in quiet, 6-unit complex - 80 STEPS TO THE WHITE SAND GULF BEACH! Newly renovated & turnkey with 3 spacious bedrooms, 3 baths, great room floor plan with open kitchen & breakfast bar. Tile and LVP flooring throughout. 2 screened balconies overlook pool, pavered and treed courtyard with partial bay view. 1 car attached garage
Jessica Russo Development Realty, LLC
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$15,000 per month
- 2 Beds
- 2 Baths
- 1,314 Sq Ft
- Condo for Rent
10475 Gulf Shore Dr Unit 142, Naples, FL 34108
10475 Gulf Shore Dr Unit 142, Naples, FL 34108Your quiet, serene beachfront retreat awaits! Take in all the beauty that Vanderbilt Beach in Naples has to offer. Enjoy a morning walk along the waters edge, a cup of coffee from the 4th floor lanai, and spectacular sunsets in the evening. With modern comforts and coastal charm, this 2 bedroom plus den, 2 bathroom condominium is sure to please. A palette of neutrals and light tones will awaken
Jodi Henderson William Raveis Real Estate
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$10,000 per month
- 2 Beds
- 2 Baths
- 1,340 Sq Ft
- Condo for Rent
11118 Gulf Shore Dr Unit 202, Naples, FL 34108
11118 Gulf Shore Dr Unit 202, Naples, FL 34108Indulge in your dream seasonal escape at this impeccably maintained condo in Vanderbilt Landings, perfectly positioned across from the pristine sands of Vanderbilt Beach with private, gated access just steps away. This bright, open, and airy residence is bathed in natural light, making it an ideal retreat for couples, small families, or anyone seeking a luxurious Florida vacation. This spacious
Vince Iorio Achieve Realty LLC
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