$5,500 per month
271 Southbay Dr Unit 53, Naples, FL 34108
Location! Gated top floor (elevator right there) condo 2 bedroom 2 bathroom all tile flooring very clean. Brand new fabulous pool, jacuzzi, lounging, boat docks. Filled with all needs. (within 2 blocks of Vanderbilt Beach, The Turtle Club, The Ritz, Buzz Lighthouse, and so much more. Tennis Courts, Gym, Shopping, Movies less than 5 blocks. Great area. By Owner. flexible lease. The longer
$10,000 per month
9103 Vanderbilt Dr Unit 2, Naples, FL 34108
Gorgeous Bay-View Rental in Naples, FL – Walk to the Beach! This beautifully appointed residential rental in Naples, Florida offers stunning unobstructed bay views, a short walk to the white-sand beaches, and access to top-tier community amenities. Perfect for those seeking comfort, convenience, and classic Naples coastal charm. Enjoy serene water views from your living room, balcony, or bedroom.
Michal Serafin Coldwell Banker Realty
$20,000 per month
236 Lagoon Ave, Naples, FL 34108
Location, Location, Location! It doesn’t get any better than this. This unique waterfront home in Conners at Vanderbilt Beach offers a spectacular 180-degree view of Vanderbilt Bay. All on one level, the residence features 3 bedrooms, 3 full baths, a 2-car garage, and 2,000 square feet of expansive living space. Enjoy hosting in the fully stocked and recently renovated chef’s kitchen with a large
Ryan Buchalter William Raveis Real Estate
$20,000 per month
9577 Gulf Shore Dr Unit 804, Naples, FL 34108
Total Renovation, Perfection, Remastered, Everything you would expect in this Contemporary Condo. Newly designed Kitchen Open Airy, quartz Counters, Custom Cabinets, Island Gathering place with Seating all while gazing out to the Beautiful Blue waters of Vanderbilt Beach. Top of the line appliances, ceiling detail and designer inspiredfurnishings add to this Winter Get Away. Primary Suite
Billie Dalesio-Faccinto Downing Frye Realty Inc.
$22,000 per month
10701 Gulf Shore Dr Unit 1102, Naples, FL 34108
Beautifully Renovated with magnificent views of the Gulf. New impact windows, sliders, etc. One open balcony for sunning and additional screened in Lanai for dining, relaxing and watching the daily Sunset that Vanderbilt beach is known for. Designer furnishings, Two ensuites, Major renovations to the building now completed following the Hurricane. Beach front pool, gated, manager on site, covered
Billie Dalesio-Faccinto Downing Frye Realty Inc.
$15,000 per month
400 Flagship Dr Unit 1104, Naples, FL 34108
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, Large lap pool, Two fitness
Domenico Ceruzzi Downing Frye Realty Inc.
$12,000 per month
410 Flagship Dr Unit 806, Naples, FL 34108
Experience Paradise at Regatta! This bright and sunny 8th-floor end unit features 3 bedrooms, 2.5 baths, plus a cozy den, offering plenty of space to relax and unwind. The tropical furnishings, fully equipped kitchen, and luxurious linens provide all the comforts of home. Many upgrades have been added in 2025. Regatta's fantastic amenities include a resort-style pool, hot tub, BBQ grills, and a
Tony Blaskis William Raveis Real Estate
$10,000 per month
10701 Gulf Shore Dr Unit 502, Naples, FL 34108
Available Jan and Apr plus all summer. Booked for Feb and Mar, 2026. Welcome to beachfront bliss at The Seville on Vanderbilt Beach! This stunning 2-bedroom, 2-bathroom condo offers the perfect combination of luxury, comfort, and coastal living. As you step inside, you're greeted by an inviting and spacious interior, adorned with modern finishes and flooded with natural light. The open floor plan
Joe Hoopfer Premier Sotheby's Int'l Realty
$9,500 per month
10475 Gulf Shore Dr Unit 132, Naples, FL 34108
Monthly seasonal rate: $9,500. Weekly rate: $2,500 + taxes (minimum 2 weeks). Beachfront Bliss in Naples Discover the ultimate Gulf-front escape at 10475 Gulf Shore Drive. This elegant mid-rise condo boasts stunning water views, a bright and open living space, and a private balcony perfect for enjoying Florida sunsets. The modern kitchen, spacious bedrooms, and master suite with en-suite bath
Bill Archer Keller Williams Realty Naples
$10,000 per month
271 Southbay Dr Unit 155, Naples, FL 34108
Come relax at this intimate gated community with 60 luxury waterfront condos, located near everything! Barefoot Pelican is a Bayfront condo development located in the popular Vanderbilt Beach area of Naples. There are two five-story complexes feature 60 units with views overlooking the Vanderbilt Lagoon. This community is just 2 minutes walking distance from Vanderbilt Beach, Naples Ritz Carlton,
Holly Gregor Royal Shell Real Estate, Inc.
$13,000 per month
9415 Gulf Shore Dr Unit 501, Naples, FL 34108
Experience luxury beachfront living at Vibrant Tides on Vanderbilt Beach, an elegantly updated 2-bedroom, 2-bath residence offering direct private beach access and sweeping Gulf views from its premier 5th-floor position. Vibrant coastal décor and upgraded furnishings create a sophisticated yet relaxed ambiance, while wide Gulf vistas and the sound of the waves elevate every moment of your stay.
Kim Dolniak Worthington Realty, Inc.
$11,000 per month
10682 Gulf Shore Dr Unit 205, Naples, FL 34108
Experience relaxation at the Monte Carlo Club! This dream rental condo features a spacious open floor plan that exudes a serene ambiance. The inviting living room offers ample space for lounging with a cozy sofa and two comfortable club chairs. Marvel at the breathtaking bay views from the comfort of your interior or step out onto your screened lanai to soak in the scenery from morning to night,
Stacey Cotter John R Wood Properties
$15,000 per month
10691 Gulf Shore Dr Unit 1101, Naples, FL 34108
$8000 per month for 2025 YEAR END SPECIAL ONLY $8000 PER MONTH UNTIL DECEMBER 31 2025. $15000 in season. Not available January 1st through April 30th, 2026. Call with any availability questions. Escape to paradise with this stunning oceanfront condo in Naples, Florida. Located directly on the Gulf of Mexico, this beautifully appointed retreat offers breathtaking views, luxurious amenities, and
Sindo Valentin LPT Realty, LLC
$7,000 per month
10701 Gulf Shore Dr Unit 702, Naples, FL 34108
Available for off season only, starting May through Nov 2026! Beautifully decorated 7th floor The Seville! Directly ON THE BEACH!! Highly sought after, rarely available high rise on the beach with dual balconies! This 2 bedroom, 2 bath condo has one long balcony overlooking the Gulf of Mexico and the other giving you city views! Community pool, tennis courts, and steps to the beach. All located
Stephanie Spooner WeichertRealtors-ParadiseHomes
$18,000 per month
9577 Gulf Shore Dr Unit 703, Naples, FL 34108
A quiet retreat on Vanderbilt Beach, 7th-floor beachfront condominium offers direct Gulf views, bay views, and private beach access. This 2-bedroom, 2-bath property features an open main living area designed to capture the western exposure. Sliding glass doors connect the living space to a large screened lanai, providing an outdoor area suitable for dining or seating. Remote-controlled solar
Kim Dolniak Worthington Realty, Inc.
$16,500 per month
9653 Gulf Shore Dr Unit 402, Naples, FL 34108
RARELY AVAILABLE... GORGEOUS, TURNKEY, FULLY RENOVATED BEACHFRONT 2 bedroom, 2 1/2-bath condo for lease at CASA GRANDE on Vanderbilt Beach. This condo has been fabulously redesigned to accommodate up to six people. This meticulously maintained home showcases incredible features including: Remote sun shade window coverings, plantation shutters, crown molding, beautiful wood flooring, custom built
David Roy Downing Frye Realty Inc.
$15,000 per month
11116 Gulf Shore Dr Unit 904, Naples, FL 34108
This beautifully renovated 9th floor end-unit condo is awash in natural light and has panoramic views of the Gulf of Mexico and Vanderbilt Bay. This property offers two bedrooms, two bathrooms and two separate lanais, each providing stunning views of the Bay and The Gulf of Mexico. The expansive master suite has views of the Gulf, an updated en-suite bath and doors that extend onto the lanai
Sarah Rosiak William Raveis Real Estate
$9,950 per month
405 Trade Winds Ave, Naples, FL 34108
405 Trade Winds Ave, Naples, FL 34108
$30,000 per month
437 Trade Winds Ave, Naples, FL 34108
Available now for long or short term rentals. Complete remodel of first floor game room and extra bedroom are completed. One of the nicest new boat dock, boat lift and jet ski lifts in Conners water front canal home. The 2nd story is the main living area with balcony overlooking the pool and spa. The kitchen has been remodeled and has a huge island. There are 3 bedrooms on the main living area.
Liz Biswurm KW Elevate Luxury
$14,000 per month
10851 Gulf Shore Dr Unit 301, Naples, FL 34108
Welcome to Vanderbilt Gulfside, one of Naples’ most loved beachfront communities, where eight acres of beautifully landscaped grounds meet the soft white sands of Vanderbilt Beach. This three-bedroom, three-bathroom corner residence captures the timeless charm of coastal Florida living — comfortable, spacious, and filled with natural light from its coveted southwest exposure. From the moment you
Bridget Sypolt Coldwell Banker Realty
$15,000 per month
9715 Gulf Shore Dr Unit 103, Naples, FL 34108
AVAILABLE ANNUALLY $6,500 PER MONTH STARTING APRIL 1ST 2026! GULF FRONTAGE LIVING AT IT'S FINEST! Enter paradise with this luxurious beachfront condominium, where the gulf's turquoise waters, coconut palms and powder-soft sands are your constant backdrop. This exceptional residence, fully renovated in 2019, offers a seamless blend of elegance and modern comfort. Enjoy breathtaking sunrise views
Kyle Johnson Coldwell Banker Realty
$14,000 per month
400 Flagship Dr Unit 704, Naples, FL 34108
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
Domenico Ceruzzi Downing Frye Realty Inc.
$4,500 per month
271 Southbay Dr Unit 153, Naples, FL 34108
Property Id: 2220943INCREDIBLE BAY VIEW and BOAT SLIP INCLUDED! Beach access is only steps away. This adorable TURNKEY condo features an updated kitchen, crown molding, and tile flooring throughout. Upgraded Impact Windows provide hurricane protection and plantation shutters give the condo an additional level of elegance. The living room has been extended and lanai closed off to provide
$15,000 per month
9051 Gulf Shore Dr Unit 3, Naples, FL 34108
AVAILABLE 2026 SEASON! Luxury, modern direct beachfront 3-bedroom penthouse residence on Vanderbilt Beach. Stunning golden sunset views from your private oversized balcony. This stylishly decorated penthouse offers 3-bedrooms and 3-full baths is perfect for a couple's winter getaway. Feel right at home with the open concept living atmosphere bursting with natural light from the gulf and bay
Jayme Bartling John R Wood Properties
$13,500 per month
400 Flagship Dr Unit 1206, Naples, FL 34108
Regatta is one of the most desired bay-front high-rise buildings in Vanderbilt Beach. Modern design concept offered by this beautiful PENTHOUSE - 3 bedroom w/3 en-suite baths - furnished with every comfort to make a rental stay more enjoyable luxury and convenience. Exquisite views of the Gulf, Bay and tropical surroundings. Recently updated with all new stainless appliances, new interior paint,
Dave Garafola Reed Property Mgt. & Sales
$18,000 per month
9577 Gulf Shore Dr Unit 601, Naples, FL 34108
6th floor, South facing Lanai, 31 bedrooms, nicely appointed, exceptionally clean, West and East facing Lanai, Upgraded granite counters as well as stainless appliances. Bright and airy the perfect place to spend the rest of 2025 and January 2026 as well as April, May. Small friendly Boutique building, gated entry, Beach side Pool and direct beach access. Walk to Laplaya, Turtle Club, Ritz
Billie Dalesio-Faccinto Downing Frye Realty Inc.
$18,000 per month
10620 Gulf Shore Dr Unit 201, Naples, FL 34108
Available for 2026 Season, with the exception of the month of February. Wake up to sparkling Gulf views and end your day with breathtaking sunsets over the water in this beautifully furnished 3-bedroom plus den, 3.5-bath condo at Beachcomber on Vanderbilt Beach. Offering 2,357 square feet of bright and inviting living space, this turnkey seasonal rental combines relaxed coastal charm with upscale
Stephanie Spooner WeichertRealtors-ParadiseHomes
$10,000 per month
400 Flagship Dr Unit 1008, Naples, FL 34108
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
Robert Alpizar Alpizar & Company, LLC
$15,000 per month
10562 Gulf Shore Dr Unit 101/102, Naples, FL 34108
ENJOY YOUR WINTER IN THIS BEAUTIFUL LUXURY CONDO, LOCATED DIRECTLY ON VANDERBILT BEACH. ***THIS CONDO IS ALSO AVAILABLE FOR PURCHASE***ENJOY THIS BEAUTIFULLY MAINTAINED 3 BEDROOMS 3 BATHS BAYFRONT CONDO, WHICH YOU WILL BE ENJOYING THE ENTIRE FIRST FLOOR. PANORAMIC VIEWS OF THE GULF AS WELL AS THE BAY. ENJOY THE HUGE GOURMET KITCHEN FOR THE CULINARY ENTHUSIAST. BEACH ACCESS FOR YOUR CONVENIENCE.
Deanna Fontes Gulf Coast Living Real Estate, Inc
$19,000 per month
10701 Gulf Shore Dr Unit 701, Naples, FL 34108
Available for November, December, and February 2026! This stunning 7th-floor beachfront condo at the exclusive Vanderbilt Shores – the Seville – offers an unforgettable seasonal escape in Naples, Florida. Wake up to panoramic Gulf views and end your days with breathtaking sunsets from your private balcony in this rare 2-bedroom, 3-bath turnkey furnished residence. Nestled in one of Naples' most
Cameron Murray WeichertRealtors-ParadiseHomes
$21,500 per month
9577 Gulf Shore Dr Unit 504, Naples, FL 34108
Complete and gorgeous renovation 3 bedrooms 2.5 baths. Sunsets 365 days, reimaged Kitchen upscale appliances designer furniture, Only unit in the building offering expanded actual laundry room and extra 1/2 bath. Westerly views and small lanai overlooking the Bay. One car attached garage. Walk to Ritz Carlton, Turtle club, Laplaya and Buzz lighthouse. Beachside pool access, gated entrance
Billie Dalesio-Faccinto Downing Frye Realty Inc.
$17,500 per month
496 Flamingo Ave, Naples, FL 34108
Owner is open to a 2-3 week leases starting in April.Renovated and updated home with high-end interior design choices. Located in the sought after area of "Conners" at Vanderbilt Beach. Minutes to the open waters of the Gulf if Mexico, glorious beaches & the exclusive Ritz Carlton. This stunning home offers amazing light and open living space, both inside and out with boat dock & lift
Joe Hoopfer Premier Sotheby's Int'l Realty
$37,500 per month
11125 Gulf Shore Dr Unit PH-7, Naples, FL 34108
Moraya Bay! Rarely available Penthouse available for the 2026 season. This 4 bedroom plus den, 3 1⁄2 bathroom condominium features over 4000 square feet with private elevator access, private garage (remote automatic) and spectacular unobstructed views of the Gulf of Mexico and Delnor-Wiggins State Park that make this property feel and live like a single family home. Nine foot ceilings, expansive
Joe Hoopfer Premier Sotheby's Int'l Realty
$14,000 per month
10475 Gulf Shore Dr Unit 114, Naples, FL 34108
Available for Jan, Feb and Mar, 2026. Also available for a minimum 2 weeks. Welcome to your beachfront paradise located in Naples, Florida! This 2-bedroom, 2-bathroom condo offers stunning views of the Gulf waters and Vanderbilt Beach's pristine white sands. Situated between Wiggins and LaPlaya, this serene retreat provides a peaceful escape from the crowds of public access beaches. Inside,
Joe Hoopfer Premier Sotheby's Int'l Realty
$8,500 per month
271 Southbay Dr Unit 123, Naples, FL 34108
Beautifully updated and maintained, this fully furnished Barefoot Pelican condo overlooks Vanderbilt Bay where you can watch the dolphins swimming by as you enjoy your morning coffee on the lanai or while having dinner. The windows throughout the condo have recently been upgraded with hurricane-proof glass and the lanai is glass enclosed. The dishwasher, A/C and Washer and Dryer were recently
Holly Gregor Royal Shell Real Estate, Inc.
$13,000 per month
9715 Gulf Shore Dr Unit 202, Naples, FL 34108
Welcome to your beachfront retreat at 9715 Gulf Shore Drive #202, where coastal sophistication meets the relaxed elegance of Naples living. Perfectly positioned along the white sands of Vanderbilt Beach, this beautifully updated residence offers breathtaking Gulf views and effortless access to the best of Naples’ waterfront lifestyle.Step inside to a bright, open-concept living space
Jake Ponsler Naples Vacation Properties
$6,500 per month
10686 Gulf Shore Dr Unit 104, Naples, FL 34108
Available Jan 2026 - April 2026! Once you are here, you won't want to go back home! In the heart of Naples beautiful coastline this property will transport you to paradise with the turn of a key! This two bed, two bath is the perfect vacation stay. Sip your favorite beverages overlooking the water and boaters along the way. This home is equipped with an open layout, perfect for entertaining and
Elizabeth Potgieter Premier Sotheby's Int'l Realty
$13,000 per month
400 Flagship Dr Unit 403, Naples, FL 34108
400 Flagship Dr Unit 403, Naples, FL 34108
$10,500 per month
9101 Vanderbilt Dr Unit 203, Naples, FL 34108
Step into the soothing rhythm of the bay at this beautifully bright and breezy 2-bedroom, 2-bath Bayfront condo, perfectly positioned within easy walking distance to the sugar-white sands of Vanderbilt Beach. With soft coastal hues, sun-drenched interiors, and tranquil bay views, this peaceful retreat offers the perfect blend of comfort, charm, and coastal elegance.Wake each morning to
Stacey Cotter John R Wood Properties
$35,000 per month
403 Seabee Ave, Naples, FL 34108
An exceptional, one-of-a-kind luxury elevator-equipped three-story retreat with Gulf-access and complete with a private dock able to accommodate a large vessel. This estate sits perfectly positioned on one of Conners’ widest canals (approximately 200 feet across), offering the waterfront lifestyle you’ve always dreamed of. Designed to impress, this architectural masterpiece showcases breathtaking
Nikki Dimitrova Florida Prime Realty, LLC
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