Home Vacation Condo Rentals By Owner In Naples, FL

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$335.46

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Cozy Condo in the only gated Golfing Community in Naples Bay!

Naples, Florida, United States

Regatta Landing in Windstar on Naples Bay is the only gated Golfing Community located in the heart of the eclectic Bayshore Arts District, placed best in the '2022 Great Places in Florida Competition'. 3 miles to 5th Ave S and 1 mile to the Botanical Gardens. Ground floor Coach Home unit completed in Nov 2020. 2beds+den, 2 baths and 2 car garage. Walk through the front door into a super-large great room with kitchen, dining area and living area. 10ft high tray ceiling, quartz tops on all counters and large island, wine cooler, GE Monogram induction cooktop, wall oven & microwave, pull out kitchen cabinet shelves. Split bedrooms with master leading, past 2 walk in closets, to a very large bathroom with separate sinks, soaking tub and large shower. Laundry room with sink, washer, dryer and storage cupboard off the great room. A short walk to the fabulous pool area with cabana, hot tub, toilets. Leave your beach chairs behind and take a walk to the shuttle dock to take the Keewaydin Queen Pontoon boat to Windstar's private beach on the Keewaydin. brbrCommunity Features Include: Beach-private, Cabana, Hot Tub, Clubhouse, Pool, Exercise Room, Short Term Golf and or Tennis Membership through Windstar.brbrRequirements: Windstar Application, Background Check and Security Deposit brbrNo Smoking or PetsbrbrOwner Pays: Electric, Water, Gas, Internet Access, Lawn Care, Management Fee, Pool Maintenance, Sewer and Trash RemovalbrbrTenants Pay: Application Fee, Association Deposit & Departure CleaningbrbrSeason Rate: $9,000brOff-Season: $5,000
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Exceptional(1)

$424.84

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Tropical Oasis in Lely Resort, Sun, Surf, Golf, Shopping and Fine Dining

Naples, Florida, United States

Plan your Naples vacation get away at Green Links in beautiful Lely Resort! This spacious and updated 2-bedroom + den villa features 1 king bed in the Master and 2 twin beds in the Guest room. It also has 2 full bathrooms and a pull out queen sofa in the den. 4 flat screen TVs, a fully equipped kitchen, washer, dryer, and free WIFI - everything you would expect to make you feel at home. This spacious condo is available to rent by the week, month or longer. The unit sleeps up to 6 people. The condo is located on the second floor which allows for a more private and peaceful setting. It has a spectacular view overlooking a large lake and the golf course. Community amenities include tight security, a heated pool/spa, grills, fitness room, clubhouse and tennis courts all within a short walk from your unit. Golf is available on site for a fee on either the Flamingo or Mustang championship courses. Ask about our discounted rates throughout the year. Dine on your lanai with the outstanding view of the golf course, lake and fountains, or stroll over to Sam Snead’s Tavern and Grill for a delicious meal. Golf, beautiful Gulf Coast beaches, unlimited shopping and dining, biking, fishing, boating, golfing, Naples Zoo, Botanical Gardens and so much more to see and do! brIf golfing is your interest, no car is needed because the condo is a three minute walk to the Lely Flamingo/Mustang club house. The condo is very close to the driving range, chipping area, practice sand trap and putting greens. It's also a great place for breakfast and lunch. The Flamingo is Naples' only Robert Trent Jones, Sr. signature course and Mustang was designed by Lee Trevino. Golf Week has twice designated the course as one of 'America's Best,' while Golf Digest and LINKS magazines gives it four stars. Naples has the highest course to golfer ratio in the US with over 35 golf courses to choose from.brGeographically located between Naples and Marco Island, Green Links at Lely Resort is only minutes (9 miles) to sunny beaches, and the incredible Naples 5th Avenue South district, which is world-renowned for its collection of bistros, art galleries, museums, and unique shopping possibilities. Downtown Naples boasts an awesome, chock-full calendar of ongoing community events, local gourmet fare, and entertainment options. Relax and renew at this wonderful resort, we think you'll consider it paradise. Thank you
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Very Good(1)

$130.61

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Cypress Woods for Seasonal or Summer Stays W Golf

Naples, Florida, United States

Summary:brOur seasonal rental condo is located in Cypress Trace of Naples, Florida and it features 18 holes of bundled golf along with pickleball, tennis, bocce, a fitness center, a lap and a free form pool along with a below ground heated spa and multiple indoor and outdoor dining options. Our condo is located on the first floor of the building and it has a lanai that you can enter from the ground level. Owner will pay all or some of the transfer fees, see below for more details.brbrThe Space:brWelcome to Your Golf Retreat in Naples, FloridabrbrEscape to the heart of Naples and indulge in a month or more of golf and leisure at our charming first-floor condo in the sought-after Cypress Woods community. With stunning views of the golf course and a host of amenities, your stay promises to be a golf enthusiast's dream.brbrAs of July 2025, the transfer fee is $950. If you’re staying for 2 months or less, the owner will cover $500 of that fee. If you’re staying 3 months or longer, the owner will cover $1,000.brbr **Comfortable Sleeping Arrangements:**br- Our condo features two spacious king bedrooms, ensuring a restful night's sleep for you and your guests.br- The main bedroom offers a serene view of the lush golf course, creating a peaceful ambiance for your stay.br- The second bedroom is located at the front of the condo, conveniently close to the second bathroom and laundry facilities.brbr **Ample Living Space:**br- Enjoy your morning coffee or a casual meal in the well-equipped kitchen with a cozy two-top dining set.br- Gather for more formal dinners at the dining table that comfortably seats four.br- Relax in the inviting family room or create your own workspace in the den.br- Savor the breathtaking sunsets from the screened and covered lanai, facing west.brbr **Community Amenities:**br- Take a short stroll to the smaller, heated community pool, just a few buildings down from your condo.br- Unwind on the pool deck, where you can soak up the sun and make the most of the warm Naples weather.brbr**Bundled Golf at Cypress Woods:**br- Cypress Woods boasts 18 holes of bundled golf designed by renowned Florida architect Gordon G. Lewis.br- This golf course weaves through cypress heads, native pine forests, rolling fairways, and offers elevated tees and greens.br- Enjoy picturesque views as you play through wetlands and nature preserves.br- Booking tee times is a breeze with the pro shop or the convenient online Chelsea system.brbr **Fitness and Sports:**br- The Fitness Center at Cypress Woods features a large heated recreational pool, a lap pool, and a hot tub for ultimate relaxation.br- Stay active with three lighted tennis courts and four lighted bocce ball courts.br- The Cypress Trace subdivision, where your unit is located, also offers a community pool.br- Explore the community's scenic walk trail for a leisurely stroll amidst nature.brbr **On-Site Dining:**br- Savor delicious meals without leaving the community at the main dining room, terrace patio, or the grille.brbr**Ideal Location:**br- Conveniently situated in the heart of north Naples, just a few minutes off I-75 and close to Immokalee Road.brbrYour Naples getaway at Cypress Woods combines golf, relaxation, and a vibrant community atmosphere. Book your stay today and create unforgettable memories in sunny Naples, FloridabrbrThere is an additional golf membership transfer fee as well as a processing fee due to Cypress Woods that is NOT included with the fees with this booking and is paid SEPARATELY. brbrImportant Details:brbr**PETS NOT ALLOWED**brbrOur condo comes with one assigned under cover parking space and there is additional guest parking in the complex by the building.brbrThis booking and reservation are contingent on the signing of a lease and HOA paperwork and approval. Access to the property can not be given until HOA approval is received prior to your move in along with the second payment, no exceptions.brbrThis is a self check in property. All fully paid reservations that have been approved by the HOA prior to arrival will receive a unique code that will allow guests to check into the property and will remain their code throughout their stay.brbrIt is best to have a vehicle with you as Naples is a large metro area. This property is about a 30 minute drive to the Fort Myers Int'l Airport. There are local bike rental shops if you are interested in getting a bike during your stay. Uber and Lyft are also readily available in the Naples area.brbrThis property and lease are managed by Bonita Springs, Florida based Mike Z Rentals, LLC. We are here to help, just let us know how we can help!brbrFlorida state permit number: #CND2103205
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$318.09

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800 South Golf Dr Unit 101

Naples, Florida, United States

Summary:brbrEscape to paradise at 800 South Gulf Dr Unit 101, walk to the beach from this stunning condominium in beautiful Naples, Florida! This inviting 2-bedroom, 2-bathroom condo offers the perfect blend of comfort and convenience. Enjoy a prime location with easy access to the beach, allowing you to soak up the sun and enjoy the ocean breeze. Featuring modern amenities, including a fully equipped kitchen, a communal pool, and comfortable living spaces, this condo is ideal for snow bird and anyone seeking a relaxing getaway. Explore nearby attractions like the Naples Zoo and the vibrant town, or simply unwind on your private patio. With its perfect location and array of amenities, 800 South Gulf Dr Unit 101 promises an unforgettable vacation experience.brbrbrbrThe Space:brbrStep inside 800 South Gulf Dr Unit 101 and discover a thoughtfully designed space perfect for your Naples getaway. The condo features two well-appointed bedrooms and two bathrooms, ensuring comfort and privacy for all guests. The Primary Bedroom offers a King Bed, providing a spacious and restful retreat. The 2nd Bedroom is furnished with a 2 single beds, offering flexibility for various guest configurations. Both bathrooms are full bathrooms. The heart of the condo is the open-concept living area, seamlessly connecting the living room, dining area, and fully equipped kitchen. This layout fosters a sense of togetherness while providing ample space for relaxation and entertainment. Step outside onto your private patio or balcony and enjoy the Florida sunshine and ocean breeze. The communal pool is available for your enjoyment. The condo is a single level home.brbrbrbrGuest Access:brbrGuests of 800 South Gulf Dr Unit 101 will have full access to the entire condo unit, including the two bedrooms, two bathrooms, the open-concept living area, dining area, and fully equipped kitchen. Enjoy the Florida sunshine and ocean breeze on your private patio or balcony. Additionally, guests are welcome to utilize the communal pool.brbrbrbrThe Neighborhood:brbrNestled in the heart of Naples, 800 South Gulf Dr Unit 101 offers an unbeatable location for your Florida getaway. You're just a short walk from the pristine sands of the beach, perfect for soaking up the sun or enjoying a leisurely stroll. For dining, explore the nearby options, with a variety of restaurants catering to all tastes, from casual eateries to upscale dining experiences. Shopaholics will appreciate the proximity to local boutiques and shops, ideal for browsing and finding unique treasures. The neighborhood is known for its relaxed atmosphere and friendly locals, creating a welcoming environment for your vacation. With easy access to both the beach and the vibrant town of Naples, you'll have everything you need for a memorable stay.brbrbrbrGetting Around:brbrGetting around 800 South Gulf Dr Unit 101 is easy! While a car is recommended to explore Naples and its surrounding areas, you'll find convenient options for transportation. Free parking is available on the premises. For those flying in, Southwest Florida International Airport (RSW) is approximately a 45-minute drive away. While public transportation options are limited in this area, ride-sharing services like Uber and Lyft are readily available for getting around. You're also within walking distance to the beach, and many local attractions are a short drive away.brbrbrbrOther Things to Note:brbrPlease note the following to ensure a smooth stay. Check-in is at 4:00 PM and check-out is at 10:00 AM. Free parking is available on the premises. This is a non-smoking condo. We are unable to accommodate pets. Please be mindful of noise levels, especially during evening hours, to respect our neighbors.brbrbrbrInteraction with Guests:brbrWe are dedicated to ensuring you have a fantastic stay. Management is generally available to assist with any questions or needs you may have throughout your visit. The best way to reach us is via the platform messaging system, as I check it frequently. I aim to respond to your messages within a few hours, but please allow up to 24 hours for a response, especially during peak times. Should you have an urgent issue, please specify 'URGENT' in your message title, and I will prioritize accordingly. I'm here to help make your Naples getaway as smooth and enjoyable as possible!
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$390.61

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Luxury 1st Floor Coach Home | Esplanade Golf, Tennis, Pickleball & Pools

Naples, Florida, United States

Truly HEAVEN ON SEVEN at Esplanade Golf & Country ClubbrbrHighlightsbr• Golf Bundled – transferable Golf & Social Membershipbr• 1st Floor Coach Home – peaceful views of the 7th hole fairwaybr• South-Facing Lanai – preferred exposure in Southwest Floridabr• 2 King Bedrooms – each with TV, plush bedding & ensuite accessbr• Queen Sofa Sleeper – memory foam mattress for extra guestsbr• Spacious Great Room – 65” TV, fireplace & dining for 6br• Chef’s Kitchen – granite counters, stainless appliances & breakfast barbr• Work-Friendly – high-speed Wi-Fi & wireless printer.br• Prime Location – 8–10 miles to beaches, 12 miles to 5th Ave, 25 miles to RSW Airportbr• Guest Perks – 2 bikes, beach chairs, beach wagon, umbrella, and more provided.brbrAbout the Coach HomebrThis newly decorated 2-bedroom, 2-bath coach home in Esplanade Golf & Country Club blends comfort and elegance. The open-concept design includes a chef’s kitchen, spacious great room, and a screened lanai overlooking the 7th hole fairway.br• Kitchen: Stainless appliances, granite counters, breakfast bar with seating for 3br• Great Room: Comfortable seating, 65” TV, electric fireplace, dining for 6, and a queen sofa sleeper with memory foam mattress for extra guestsbr• Primary Suite: King bed, 65” TV, walk-in closet, ensuite bath with walk-in shower, plantation shutters, LED remote ceiling fanbr• Guest Suite: King bed, 55” TV, jack-and-jill bath, generous closet/storage, plantation shutters, LED remote ceiling fanbr• Extras: High-speed Wi-Fi, wireless printer, newer washer/dryer, private garage, 2 bicycles, beach chairs, beach wagon, umbrella, and morebrbrbrOutdoor LivingbrThe south-facing screened lanai provides the preferred exposure in Southwest Florida—bright and sunny year-round without the intense afternoon heat. Perfect for enjoying coffee in the morning, working during the day, or sipping wine in the evening. Sun-blocking shades, cozy seating, and a dining table make this an ideal spot for relaxation or meals with a view of the 7th hole.brbrResort-Style AmenitiesbrWith transferable Golf & Social Membership, you will have access to:br• Championship golf coursebr• Resort-style pool with cabanas.br• Tennis and pickleball courtsbr• Spa and fitness centerbr• On-site dining and barsbr• Full Time Activities Director that plans events and activities for the community.brbrLocationbrOne of the best features of this coach home is its prime location within Esplanade:br• Just down the street from the Bellano Satellite Pool for quick dips or loungingbr• A short walk or bike ride to the main resort campus with pools, fitness, spa, dining, and activitiesbr• 8–10 miles to Gulf Coast beachesbr• 12 miles to Naples’ famous 5th Avenue Downtownbr• 25 miles to RSW International Airportbr• It is surrounded by North Naples dining, shopping, and conveniences.brbrThis is not your average rental—it is a 5-star retreat designed for guests seeking both relaxation and resort-style living.brbr***************************************************************************** brPayment Schedule Payment amount brUpon Execution of Agreement: 30% of Total Amount Due br180 Days Prior to Check-In: 30% of Total Amount Due brFinal Payment 120 Days Prior to Check-In: 40% of Total Amount Due brbrRefundable Security Deposit by Check is due 30 Days Prior to Check In/Or Optional Credit Card Hold 10 days prior to Check In. Refer to Contract amount /Or Per VRBO brbrPayment Examples: With Less than 180 days: A reservation made 179 days before arrival Renter must make first and second payment at the same time for a total of 60% of rental charges. A reservation made less than 119 days from arrival must make full payment. brbrCancellation Policy: Please refer to contract. HOA Fees are subject to change and may be charged to renter.
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Exceptional(1)

$299.3

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Resort Living, Professionally Decorated, END Unit,1st Floor, Stunning Water View

Naples, Florida, United States

Enjoy a peaceful cup of coffee in the morning or enjoy stunning sunsets in the evening on the cozy lanai over looking the golf course and water views.brbrThe spacious ensuite master bedroom has a comfortable king bed with high end sheets and bedding and an ensuite bathroom with ample closet space, a separate toilet room, and a large walk-in shower. Double sinks and plenty of towels and toiletries to get your stay started.brbrBedroom 2 has a comfy queen size bed and lots of storage space. Extra pillows and blankets provided for your comfort.brbrDen/office area allows you to stay connected while disconnecting. Work space and comfort in one.brbrEverything about this end unit1st floor condo feels serene and peaceful. As you relax on your comfortable lanai you will see amazing western sunsets overlooking the lake.brbrHOA Application process and rules apply.brbr***************************************************************************** brPayment Schedule Payment amount brUpon Execution of Agreement: 30% of Total Amount Due br180 Days Prior to Check-In: 30% of Total Amount Due brFinal Payment 120 Days Prior to Check-In: 40% of Total Amount Due brRefundable Security Deposit by Check is due 30 Days Prior to Check In/Or Optional Credit Card Hold 10 days prior to Check In. Refer to Contract amount /Or Per VRBO brbrPayment Examples: With Less than 180 days: A reservation made 179 days before arrival Renter must make first and second payment at the same time for a total of 60% of rental charges. A reservation made less than 119 days from arrival must make full payment. brbrCancellation Policy: Please refer to contract. HOA Fees are subject to change and may be charged to renter.
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Exceptional(1)

$704.78

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Luxury BEACHFRONT -The Villas of Vanderbilt - 2BDRM Plus Den

Naples, Florida, United States

Welcome to our oasis on Vanderbilt Beach, where luxury meets coastal living. Enjoy your stylish condo located along the beautiful Gulf of Mexico's shoreline with white sandy beaches and amazing sunset views. Enjoy all the comforts of home in our spacious 2-bedroom, 2 bathrooms plus den available for you to spread out. Sit on our patio to enjoy the breeze and hear the waves crashing while you take in the amazing sunset views. Fantastic location just two doors down from LaPlaya! Tennis and Pickleball available to use.br br Fully updated condo located just steps away from LaPlaya on Vanderbilt Beach. Wiggins State Park just to your north and The Ritz Carlton to your south our condo has a Prime Naples address.brMaster bedroom has amazing gulf views to wake up to and furnished with a plush king-sized bed, large walk-in closet and attached bath with dual sinks and updated walk-in shower. Open Concept Kitchen, Dining and Living Room leading out to our Beachfront Balcony. Guest Bedroom furnished with a queen-sized bed, large closet and great bay views across the street which provide stunning sunrises. Guest bath adjacent to second bedroom making it the prefect guest quarters. Den comfortably furnished with a desk, sofa and TV, also offering sunrises over the bay. Laundry in condo, ample storage throughout. The kitchen is well stocked with everything you need to cook and entertain. Beach equipment provided including Beach Chairs, Towels, Cart and Umbrella.brAll linens and towels provided brbr1 Parking space provided in our parking garage just across the street. Tennis and Pickleball are available located on the rooftop of parking garage.brbrPlease note: brbrAll Towels/Linens are provided.brbrThis unit comes with a starter set of toiletries and paper products for your convenience to help you settle into your relaxing getaway. Please note that these items are not replenished once depleted.brbrIn Unit Washer and Dryer are provided. brbrThere will be some shared spaces such as pool, elevators, etc.brbrWe provide full service: We will meet our guest's at check in to make sure they find everything they need and provide keys to our condo. brbrWe will be available through booking site inbox, email, text and phone calls as well.brbrNo Pet Allowed: Service Animals permitted with proper paperwork submitted prior to arrival date. brbrNo Parties Allowed. brbrThis unit has a King bed in the Master bedroom and a Queen bed in the 2nd bedroom. brbrThis unit comes with a starter set of toiletries and paper products for your convenience to help you settle into your relaxing getaway. Please note that these items are not replenished once depleted.brbrOur pool is expected to open December 2025 but is still fluid for an exact open date.brbrDisclaimer: You are renting a private condo in a shared area.br br60 Night Min Stay is required, and Condo Approval is Required
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$140.23

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Lovely 2 BR, 2 BA condo in paradise @ The Glades!

Naples, Florida, United States

Truly Naples Paradise at this second floor unit in a quiet alcove far from the main parking area. The Glades offers a very active lifestyle and is a short drive to 5th Avenue for dining and shopping, as well as the beaches on the Gulf of Mexico. So many amenities!brNine heated pools andbrTwo golf courses:br•The Pines is our 18-hole par 70 course.br•The Palmetto is our 18-hole by 55 executive course, an exceptional by 3 course.brThe spacebrThe condo has 2 spacious bedrooms, one king and one queen. Open kitchen to dining area and living room with large TV. Enjoy the convenience of in-unit laundry, walk in closet, and a master bathroom that has the sinks set apart from the private bathroom. Living room opens to 2 adjoined screened lanais overlooking a lovely water stream. This double screened lanai offers plenty of space for cozy outdoor dining and drinks.brGuest accessbrThere are NINE pools at the Glades. Other amenities include Pickleball, tennis, bocce, and shuffleboard. The 19th Hole restaurant, Pro shop, and Clubhouse offer many activities during the winter season. Guests of the Glades enjoy golf on two recently renovated Gordon Lewis designed golf courses the par 70 (The Pines) and the par 55 (The Palmetto). This condo is minutes from the many beautiful beaches in Naples!brOther things to notebrGuests must submit an application to the Glades with a $150 fee that covers parking and use of the many Glades amenities.brThe main pool has poolside service and a great restaurant.brA $250 security deposit is collected for 30 days or less and returned upon departure.brA $500 security deposit will be collected for greater than 30 day reservations and returned upon departure.
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$140.86

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Charming Cardinal Cove 2-bed, 2-bath, 2-car garage villa at Fiddler's Creek.

Naples, Florida, United States

Experience the Naples area to its fullest in this updated single-story attached villa with a two-car garage. The condo is located within the award-winning, private, master-planned community of Fiddler's Creek, in the Cardinal Cove community, and is convenient to Marco Island and Naples beaches. brbrThe open floor plan provides ample room for lounging and dining with updated and modern kitchen, baths, and furnishings. The spacious primary bedroom features a comfortable office area, television, fan, a luxury king bed, a private bath with two individual sink areas, a bathtub, a shower, and a water closet. There is a large walk-in closet for all your belongings and resort wear. The second bedroom has a comfortable queen bed, television, fan, and an adjacent full bath. brbrThe rental has several niceties, including linens, beach towels, floats, beach toys, coolers, games, puzzles, and a child stroller.brbrOther amenities include a washer/dryer, appliances, two refrigerators/freezers, and a fully equipped kitchen with dishware, Keurig, and cooking utensils. brbrYou will enjoy outdoor living on the front dining lanai and the rear relaxing and reclining lanai. A short walk away, 44 residential units share a nice-sized community pool. Fiddler's Creek maintains miles of walking, running, and biking paths. brbrPlease note this rental does not permit pets or smoking. brbrThe minimum rental period in this community is 30 days, and we welcome longer stays. For an optional one-time transfer fee of $750/stay, you can enjoy a wealth of resort-style amenities, including three resort-style pools with beverage and towel service, dining, a full-service spa, tennis center, pickleball, gym, exercise classes, and activities and social events at the clubhouse. brbrWhen you stay at our place, you can enjoy all that Naples has to offer. Our condo provides easy access to world-class shopping and dining destinations on Naples' famous Third Street South and Fifth Avenue. You will also be minutes away from fishing, boating, exploring, and enjoying waterways and beaches.
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