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Are you looking for a sunny getaway? Our monthly rentals in Naples, Florida, offer a perfect escape. Whether you're seeking a winter retreat or a long-term stay, Naples has it all. From stunning beaches to world-class golf courses, there’s something for everyone.
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Spacious 3 bdrm/3 bath condo in fabulous Vanderbilt beach location, just a 5 minutes walk from the beach. Watch beautiful sunsets from your lanai on the fourth floor of Regatta. This is a gated community with Resort style amenities, including a beautiful landscaped waterfall pool, a lap pool, a hot tub,...
Featured review
Greatly enjoyed our recent stay at this spacious rental at the Regatta. Perfectly situated within a very short walk to Vanderbilt Beach and an easy drive to restaurants and shops. The unit has just been...
Distance to beach: 3 miles to Public Beach, 5000 Gulf Shore Blvd N, Naples
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Renovated condo with the new stainless steel appliances in the best location in Naples, Florida. 3 miles to the beach, very close to great restaurants, Costco, Walmart, Target, Publix, Waterside shops, only 10 minutes to 5th Avenue. Enjoy the club house with resort style community pool, BBQ area, billiards,...
Featured review
The location is awesome, and communication was super easy. The unit is really clean, well-kept, and offers amazing views. It's also close to local attractions and great spots to explore. Would definitely...
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Open-concept 1,450 square feet all located on ground floor with access from double car garage. On each side of spacious living area you'll find two King suites with screened-in lanai on each. Master suite includes walk-in bathroom with large glass shower. Ensuite privilege for guest King suite with...
Featured review
My wife and I really enjoyed our time at this location. It had all sorts of extra like bicycles, chairs for the clubs, etc. etc. And the pool unbelievable waiter service to the poolside drinks food .We...
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This home is truly what living in Olde Naples is all about! A spacious home great for entertaining, enjoy the outdoors on the verandah or out by the pool, walk to the beach, and easily enjoy Fifth Ave and Third street shopping, dining and entertainment! Wonderful & well-built in 2007! Open & bright,...
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Look out your window to see a stunning view of the Gulf, have breakfast, enjoy the beach or a stroll down the Naples Pier. The Pier at night is amazing--enjoy a 360 degree view of the ocean under the stars or come home to relax on the rooftop deck and enjoy the night sky.The Pier House is stunning...
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Why settle for ordinary when you can have EXTRAORDINARY-the BEST of the BEST for your Naples getaway! Experience the epitome of coastal luxury in this three-story GULF-access estate home with a private dock and boat lift, perfectly positioned on the widest canal in the prestigious Conners neighborhood...
Distance to beach: 4 miles to Vanderbilt beach
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Bridgewater Bay of Naples, one of Naples' most desirable communities. This stunning first floor coach home harmoniously blends comfort and style to enjoy Florida's lifestyle. With nearly 1800 sq ft of living space with an open concept. The large Panoramic window is undoubtedly the center piece...
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Welcome to The Cambier Cottage, a charming vacation home nestled in the heart of Olde Naples, Florida. This delightful retreat seamlessly combines comfort, convenience, and artistic flair. Expertly handcrafted by a talented local Naples artist, every corner of this three-bedroom, three-bathroom haven...
Distance to beach: 7 miles to Naples Pier
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A well-appointed 3 bedroom, 2 bath condo overlooking one of Treviso Bay's peaceful ponds. Step outside from the ground floor and take the short walk (15 seconds) down to the eight Pickleball courts and beautiful swimming pool. Treviso Bay is one of Naples’ Premier Luxury/Amenity communities....
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The home is located on Duck Chanell, Aqualane Shores, Naples. At the bottom of the street is the Gulf of Mexico incredible beaches.Three bedroom (King, Queen, two double beds). Three full bathrooms. The living room has a fold out sofa bed.The home is extensively renovated. A beautiful pool...
Distance to beach: 0.1 miles to 1 block
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This newly renovated condo is on Hurricane Bay, just one block from the popular Lowdermilk Park on the Gulf of Mexico. No need to drive to the beach - it's right in your back yard! Coquina Cove is a small boutique complex of 18 units. It has a beautiful pool overlooking the bay, where you see...
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A rare opportunity located in the heart of Old Naples at $55,000/month in season. This three-level residence offers simple and crisp spaces, creating a seamless flow from room to room with white limestone floors, imported Italian wood and glass custom doors and custom cabinetry in the kitchen and baths....
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Welcome to your own slice of paradise in Naples, Florida. Nestled in a prime location, just 5 blocks away from the vibrant 5th Avenue shops and restaurants, and a mere 2 blocks from the sun-kissed beach, this opulent 3-story estate is a dream come true. With 6 spacious bedrooms, this residence exudes...
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The Captain's Cottage is a everything you hope for when staying in Naples! The home is a spacious five bedroom villa with a large pool overlooking a waterfront view. This property has been designed with an elegant coastal vibe with plenty of areas to entertain and relax. Located in Naples' famous...
Distance to beach: 2 miles to Lowdermilk Park
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This tranquil Vacation Lakefront home is centrally located in the heart of Naples. Biking distance to our world famous beaches (Lowdermilk/Clampass), Naples Zoo Naples Beach Hotel & Golf Club. Just a 5 minute drive to 5th and 3rd Avenues for the best shopping and restaurant experience. This single...
Featured review
We were fortunate to have spent a month in the serene and beautifully decorated Lake house. So accessible and only minutes from our favorite Naples beach. The house was comfortable, well-equipped and the...
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This home is truly what living in Olde Naples is all about! A spacious home great for entertaining, enjoy the outdoors on the verandah or out by the pool, walk to the beach, and easily enjoy Fifth Ave and Third street shopping, dining and entertainment! Open & bright, loaded w/upgrades! Absolutely...
Distance to beach: 0.2 miles to Naples
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Breathtaking Views of the Gulf from an expansive 8th-floor lanai, and an enviable location steps away from beaches at Delnor-Wiggins State Park are all wrapped up in this bright Vanderbilt Towers Penthouse residence. The immaculate turn-key furnished condo has tile floors throughout and features an open...
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Gulf Pavillion SummarSummary: Escape to the Gulf Pavillion, a stunning condominium in Naples, Florida, offering luxurious comfort and breathtaking water views. This 2-bedroom, 2-bathroom retreat is perfect for families, with amenities like a communal pool, beach access, and a fully equipped kitchen....
Distance to beach: 1 miles to Vanderbilt Beach
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DEC, JAN, FEB, MAR 2026 are NOW available! Off-season weekly rates available upon request. ALL INCLUSIVE monthly rate May to Dec 19th $4,960. Dec 19th to Apr $8,000 (rent, tax, cleaning, utilities, cable/wifi, pool heat, damage waiver all included). Naples FL vacation rental.PRIVATE HEATED POOL –...
Featured review
Our first visit to Naples was enjoyed so much because of this wonderful home in a quiet neighborhood. The location allowed for short trips to a couple of beaches, and to many nice restaurants and shopping...
Distance to beach: 1 miles to Naples
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This luxurious 3,000 square foot home is located in an upscale Naples neighborhood. Walk or bike to the beach or many local shops and restaurants. Swim in a 36’ heated, salt water pool. Lounge or barbecue in the large screened lanai. Lanai furniture provides dining for 8, cafe seating for 2,...
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Experience the ultimate beach getaway in this meticulously updated Naples Park beach house. Located on the coveted 500 block, mere minutes from Vanderbilt Beach, this charming abode offers a spacious layout with two serene guest bedrooms upstairs and a cozy master bedroom on the main level. Immaculately...
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This home is located only three blocks from the beach! Enjoy a beautiful back yard living space, completely enclosed by greenery for privacy and beauty while you enjoy the pool, hot tub, or fire pit along with full outdoor grilling area. Renovated interior with an open kitchen / living room, this home...
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Welcome to Glen Eagle Golf and Country Club—a modern masterpiece that blends luxury with comfort. This fully furnished villa is a larger model, featuring 2 bedrooms plus a den (which can be used as a third bedroom), 2 bathrooms, and a 2-car garage, all set on a spacious .26-acre lot.***CURRENTLY...
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This spacious condo is the perfect home base for your trip to Naples. Enjoy all the amenities of the Cypress Woods Country Club and a short drive to gorgeous, warm beaches. Naples boasts a lively downtown with lots of shopping, restaurants and beautifully maintained streets for strolls in the evening....
Featured review
This condo is in a gated golf community. We transferred the golf membership and golfed and used their fitness facility. The condo had everything we needed. Two negatives. The noise from highway 75 when...
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Enjoy our 3-bedroom + office, 2-bathroom home in the Glen Eagle Golf and Country Club community of Naples. Enjoy stunning views of the 10th green and 11th tee box right from your private pool and hot tub. Home has been completely renovated from top to bottom. Monthly rentals only - golf membership is...
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Conveniently located just minutes away from Vanderbilt beach and downtown Naples, our home serves as the ideal base for your adventures in Naples. Whether you're here for business or pleasure, you'll find everything you need for a memorable stay. We look forward to hosting you!If traveling...
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Wake up every morning to outstanding sunrises over Moorings Bay. Spindrift is located on Gulf Shore Blvd N across from Miramar Beach in Naples proper. This unique condo was owner occupied so it is decorated and maintained in a manner unlike typical rental properties. Both bedrooms boast king size beds...
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The Bamboo Bungalow is what living in Naples is all about! Located in Lake Park, just a short drive or bike ride to the beach and fifth avenue. This Lake Front house has one bedroom with a king size bed and den with two Queen size sleeper sofas, and 2 on suite bathrooms, as well as a guest house with...
Distance to beach: 9 miles to Vanderbilt Beach
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A fully furnished Veranda I Condominium in beautiful Heritage Bay (HB) is available for annual rental, or seasonal rental, effective through all of 2025-7. This is a 2-bedroom unit with a Den/Office that also has a pull-out sofa bed. Rental also includes a 1 car unattached garage. Full golf membership...
Featured review
Our stay at this rental was awesome! We lacked for nothing in this fabulous space. Jim has thought of everything!
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La Dolce Vita..savour the Naples sweet life in Coral Falls. Newly finished luxury VP flooring in living and bedrooms. Imagine sipping coffee in the morning or wine in the evening on the luxurious lanai with a view of the tranquil preserve. Let it relax you before and after spending time at the pool and...
Featured review
This condo was just perfect for my husband and me. Although it was so close to major roads and shopping amenities, it was very quiet, looking over palm trees, a patio area with covered over picnic tables,...
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You will love this beautiful and tastefully decorated house in the highly desirable neighborhood of Naples Park in Naples, Florida! Naples Park is a non gated area located walking distance to the beach and Mercato. The house is furnished with your comfort in mind. The master bedroom is en suite with...
Featured review
What a beautiful home! We loved every minute of our stay. Everything is brand new, and so stylish. You can walk to the beach, there are two amazing beaches to pick from. The one with the Ritz was so nice....
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Welcome to your slice of paradise along the pristine shores of the Gulf in Naples, Florida. This beach front condo, located in the community of Park Shore, offers breathtaking Gulf views from every room and all the comforts of home. The condo is an end unit in the building located on the 9th floor - you...
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Welcome! The home has a media area with a large-screen TV, a lanai with pool, full kitchen and dining area with seating for 8, and a small office/breakfast nook.There are 4 bedrooms and 3 bathrooms in the house: A Master suite, an in-law suite, and two smaller rooms to the front that share the remaining...
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Welcome to Bolero Oasis - In the heart if Naples - Close to Beaches and RestaurantSummary: Escape to this stunning three-bedroom, two-bathroom pool home located in the heart of beautiful Naples, Florida. Whether you’re here for a family vacation, a romantic retreat, or a fun getaway with friends,...
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The Coconut Plantation is the pinnacle of Naples luxury living. Prepared to be enchanted upon arrival as you are greeted by a lush landscape. Royal Poinciana frame this plantation style house that overflows with southern charm. A brick paver circular driveway provides the gateway to this southern style...
Distance to beach: 8 miles to Naples Pier
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Paradise Awaits at Your Coral Falls Getaway at Lely Resort - Heated Pool Always set to 89 degrees! 1st Floor and steps from the Heated Pool with a Waterfall! Best Location in all of Lely! Kick back and relax in this calm, beautifully redesigned space. Relax on the Lanai that looks out onto a nature preserve...
Featured review
Thank you for a wonderful holiday in your beautiful condo. It was a great location for both Naples and Marco island. The pool being steps away from the Lanai was a welcome place after a day sightseeing...
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As soon as you pull into Tarpon cove, a gated community in the Vanderbilt neighborhood of North Naples, you will know you are home. Lush landscaping, pools, lakes and a natural preserve adorn the property. This 2nd floor Bimini model 3 bed, 2 full bath plus a den with a sofa bed sleeps 8 and contains...
Featured review
Wonderful rental beautiful spacious and everything we could need. We will be returning. Can’t recommend this enough
Distance to beach: 1 miles to 1st Avenue Beach
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Gorgeously furnished oversized fifth floor two bedroom with balcony and sunset views. 1111 Central development offers large zero entry pool with two spas, thoroughly equipped gym, game room, theatre room, co-working space, BBQ facilities and much more!15 minute walk to beach, 10 minute walk to 5th...
Distance to beach: 2 miles to Clam Pass
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Location, location and everything you could ask for at this beautiful, centrally located condo in the most convenient location in all of Naples. Truly a gem, this freshly renovated condo enjoys tranquil western facing sunset views and quiet nature where you can watch golfers putt on the green and tee...
Distance to beach: 10 miles to Tigertail Beach, Marco Island
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FULL GOLF MEMBERSHIP IS NOW AVAILABLEOct 2025 $5k/mo Nov 2025 - Apr 2026 N/A May 2026 $8k/mo ask about other monthsThe social member benefits are included in rental fee, full golf rental membership is available for an additional fee per Eagle Creek Golf and Country Club rules (currently plus...
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Escape to Naples, Florida — recently ranked the #1 Best Place to Live in the U.S. (U.S. News & World Report)! Enjoy your winter in a newly purchased, fully renovated first-floor condo with all-new warm, seashore-inspired beach décor. This retreat is fully stocked with name-brand appliances,...
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The Aqua is a brand new waterfront home on Crane Channel in Old Naples Aqualane Shores neighborhood. Be prepared for opulence, elegance and an extravagantly affluent property. Experience Naples living at its finest with this 4 Bedroom, 4.5 bath home. The Aqua has been designed with a modern flair and...
Distance to beach: 7 miles to Naples Beach
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Updated ground floor 2 bedroom, 2 full bath condo in the Countryside Golf and Country Club community available for seasonal rentals with a view of the lake and the 14th fairway and green. Condo is fully furnished with new appliances and equipped with all you would need for your home away from home. Washer...
Featured review
Our experience at Endless Summer Vacation Home was nothing short of spectacular! From the moment we arrived, we felt incredibly welcomed and at home.The host was kind and exceptionally responsive, providing...
Distance to beach: 3 miles to Delnor Wiggins State Park Beach
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Enjoy this centrally located 3 bed 2 bath coach style condo. Charleston Square is a small community located in Imperial Golf Estates. Our condo overlooks the prestigious Gomez Tennis Academy. We're also just a few minutes to Wiggins Pass Beach State Park, Barefoot Beach, and Bonita Beach. Very...
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This beautiful condo is located in the extremely desirable active Huntington Lakes, which is just minutes from all of the amazing shops, restaurants and the BEACH! This 2-bedroom condo, is fully FURNISHED and stocked with everything that is needed. It is a gated community with plenty of activities such...
Distance to beach: 2 miles to Clam Pass
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** We are fully booked now through December 31, 2025.Golf Course By The Sea #2 - Penthouse Near the Beach!Golf Course By The Sea #1 - the original condo in this complex was and continues to be such a hit, we have added a new (secondary) condo top floor in the same complex - hence - Gulf Course...
Featured review
Thank you to this host for a most wonderful first-time non hotel longer-term rental experience. We will never return to a hotel after experiencing such a wonderful condo stay at a fraction of the cost...
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Spacious 1st floor condo-amazing golf views, fully furnished. New hardwood floors, new Master bedroom with King bed, New Queen bed in 2nd BR with New dream-like mattresses. Murphy console-LR makes to Queen for extra sleeping. Both bathrooms/closets completely redone very stylishly. Desk for working...
Distance to beach: 1 miles to Jacks
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Naples North - This condo is professionally decorated and shows beautifully, it has 2 outdoor seating areas, one that overlooks the lake with Pine Trees and Palms, the other is at the ront of condo as you enter the front door. The entire condo has been totally renovated. The condo is equipped with...
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THIS UNIT IS AVAILABLE FOR JAN/FEB/MARCH/APRIL of 2025This beautiful 3 bedroom 2 bath condo is professionally decorated and immaculately kept to perfection. The bedrooms are equipped with a King bed in the master bedroom, and Queen beds in the guest bedrooms. The Great Room features a 60" Television,...
Featured review
Wonderful condo. Comfortable, clean, great location. Love everything about this place and the Dunes
Distance to beach: 8 miles to Naples Pier
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Heated Pool Always set to 89 degrees! Beautiful backyard scenery surrounded by a nature preserve. New white kitchen with quartz counters & stainless appliances. Both bathrooms were renovated. Open floorplan, dining area, family room, light & bright, views of lanai and pool area. Primary bedroom...
Explore a diverse selection of monthly rentals tailored to meet your needs. Whether you prefer a cozy condo close to the bustling downtown or a spacious home near the tranquil beaches, Naples has a variety of options to choose from. Enjoy the flexibility and comfort of a long-term rental in this beautiful coastal city.
Don’t miss the chance to stay in one of the most desirable locations in Florida. Browse our listings for monthly rentals in Naples and find the perfect place for your extended stay. With a variety of options to choose from, you’re sure to find a rental that fits your needs and makes your stay in Naples unforgettable.
Thinking about next year? Secure your spot now for seasonal rentals and ensure you get the best accommodations for your stay. Whether you’re planning a winter escape or a long-term summer visit, booking early guarantees you the perfect rental.
Discover the Perfect Monthly Rental for Your Group
Planning a getaway with a medium-sized or large group in Naples? Our selection of monthly rentals includes spacious homes designed for groups of 8 or more people. Find the ideal accommodation complete with private pools, large kitchens, and ample space to relax and enjoy. Explore options with 7+ bedrooms and multiple bathrooms to ensure everyone has room to unwind.
Family-Friendly Monthly Rentals
Looking to plan a large family trip? Naples offers numerous family-friendly monthly rentals equipped with amenities like private pools, game rooms, and hot tubs. Enjoy activities such as biking, swimming, hiking, and more. Find roomy rentals that can comfortably house a large family with five or more beds and multiple bathrooms. Start your search now to find the perfect family-friendly rental in Naples.
Romantic Getaways for Couples
Browse our best offers for couples seeking a private getaway in Naples. Enjoy relaxing activities like hiking, swimming, and biking. Our romantic monthly rentals come equipped with jacuzzis, spas, and picturesque views of Naples' beautiful scenery. Plan your couple's retreat and find the perfect place to create unforgettable memories.
Winter Retreats in Naples
Escape the cold and enjoy the warmth of Naples during the winter months. Our monthly rentals are perfect for snowbirds looking to spend the winter in a sunny and pleasant climate. With average temperatures ranging from the mid-60s to mid-70s Fahrenheit, Naples offers an inviting escape from the winter chill.
Why Naples is Perfect for Snowbirds
Book Your Winter Stay Now
Secure your winter retreat in Naples by booking one of our monthly rentals. Enjoy the best that Naples has to offer and make your winter getaway a memorable experience. Explore our listings and find the perfect home away from home for your winter escape.
Naples boasts some of the most beautiful beaches in Florida, making it a paradise for beach lovers. When you stay in one of our monthly rentals, you'll have easy access to a variety of beach activities:
Explore our listings today to find the perfect monthly rental in Naples, Florida, and make the most of your beachside getaway!
💰 Highest rates
In March
🎉 Busiest month
January
🏠 Popular home types
Condo and House rental
🔥 Hottest months
July and August
❄️ Coldest months
January and December
☔ Rainiest months
June and August
🌺 Best months for flowers
April and May
🌴 Peak tourist season
December to April
🍂 Quietest months
September and October
🌊 Best beach months
April and May
🏌️ Best golfing months
November to April
🎨 Top cultural events
Naples Winter Wine Festival (January), Naples National Art Festival (February)
🍽️ Best dining months
January to March (Restaurant Weeks)
🦋 Nature activities peak
March to May (Butterfly watching and bird migrations)
🛶 Water sports season
June to September
🏖️ Best months for shelling
May and June
📅 Local festivals peak
December to April
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