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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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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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Single Family. Park Model on the lake Livingroom - Kitchen - Dining Room - Bedroom Patio overlooking lake Includes all utilities & WiFi 55 And over Gates Community 2 Swimming Pools, Hot Tob, Tennis, Pickle Ball Courts Horse Shoes, Shuffle Board Community Center Parking for 2 Cars
Distance to beach: 10 miles to Tigertail Beach, Marco Island
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FULL GOLF MEMBERSHIP IS NOW AVAILABLEMay 2026 $5k/mo Jun-Oct 2026 $4.5k/mo Nov 2026 - Apr 2027 N/A May 2027 $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...
Distance to beach: 4 miles to Vanderbilt Beach
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This comfortable and well-appointed home is designed for easy, longer stays—whether you're here for a week, a month, or just need a peaceful break.With plenty of space to spread out, a fully equipped kitchen, and inviting indoor/outdoor living areas, it’s ideal for couples, families,...
Featured review
This house was clean and located perfectly near all the beaches , shopping and restaurants! The back yard was paradise with a pool , jacuzzi and lanai with TV ! We can’t wait to go back !
Distance to beach: 10 miles to Vanderbilt Beach
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At just $14,000/month in season, this gorgeous and spacious Golden Gate Estates pet-friendly single family home has 4 bedrooms, den, 3.5 baths, and stunning upgrades everywhere you look! Start with the curb appeal and lush landscaping, then go inside where you will find a light and bright open floor plan...
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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: 3 miles to VANDERBUILT BEACH
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This meticulously maintained first-floor condo is situated on the 16th hole of a pristine golf course, offering picturesque views of both the serene lake and lush fairways. The property features two well-appointed bedrooms, two bathrooms, and a spacious den, providing ample living space. A large lanai...
Distance to beach: 1 miles to Vanderbilt Beach
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BRAND NEW ON THE RENTAL MARKET WITH AN OPEN CALENDAR FOR YOU TO CHOOSE YOUR PREFERED DATES!! Beautiful 3 bedroom home with southern exposure located in the desirable 600 block. Walk, cruiser bike or take our local shuttle service to Vanderbilt Beach! This home offers an open floor plan, high ceilings,...
Featured review
We loved this home! The location in north Naples was ideal- close to Mercato, Vanderbilt Beach / Wiggins state park. The home is EXCEPTIONALLY well equipped in every way from PLENTY of beach towels, to...
Distance to beach: 10 miles to Naples and Marco Island
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Our second floor condo in Coral falls, Lely, Naples has a bright and spacious feel, beautiful views and has all your needs for your home away from home while. The building is equipped with an elevator, as well as two separate stair cases. The primary suite sleeps two in its King size bed. The EnSuite...
Featured review
! had the most relaxing stay at this Florida condo! The location couldn’t be better—just a quick drive to beaches, shopping and dining.The condo was spotless, stylish, and incredibly cozy. I loved...
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AVAILABLE from April 1st 2026 !!! Minimum 1 month rent. Great location !!! Clean and neat first floor 3 bedrooms, 2 full baths unit in Coach Home. No stairs. Beautifully remodeled. Plank tile, freshly painted, new stainless steel appliances, quartz countertop, recess lights, fully equipped kitchen, two...
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Great location in Olde Naples! Third floor 2 bed, 1.5 bath condo just a short walk to the beach or 5th Ave South. This west-facing unit overlooks a quiet street lined with palm trees. Amenities include a community pool (heated in winter) and lounge deck, elevator access, designated parking, and on-site...
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RATES for 2026One month minimum rental in season January 2026 $7,000 February 2026 Booked March 2026 $7250 April 2026 $4500Plus taxes and $150 HOA approval feeCALL ME WITH ANY QUESTIONS...
Distance to beach: 250 feet to Vanderbilt Beach
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This 2 BR condo is located in a gated community alongside Vanderbilt Beach.The condo has been updated with newer tiled bathrooms and furnishings. The spacious lanai has all-weather wicker furniture to enjoy coffee with the morning sunrise or a quiet evening after a day at the beach. Lanai includes...
Featured review
Everything you need at your fingertips- all you need is to bring sunscreen and beachwear! Beautiful condo.
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Available starting December 19 through February 14 and from March 15 to April 30, 2026. Courtyard Home in Masters Reserve at Lely Resort -an Ideal Vacation Retreat! This beautifully furnished home is located in one of Naples’ most desirable resort communities, the exclusive Masters Reserve at Lely...
Distance to beach: 0.5 miles to Wiggins Pass
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As soon as you arrive at Princeton Place in the Vanderbilt neighborhood of North Naples, you know you are at home. Beautiful, lush landscaping, lawns, pool, pond, and boat docks adorn this property. In addition, you will have access to the optional membership at the Tarpon Cove Yacht and Racquet Club....
Featured review
Location was excellent and the condo was great. Everything was as advertised and then some. Chip, the owner, was very nice and responded very quickly to all questions and requests we had. Quiet area with...
Distance to beach: 5 miles to Naples Beach
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Fabulous two bedroom two bathroom apartment (master with California king bed and second bedroom with queen bed) with enclosed lanai overlooking second tee and lake. Turn key and fully equipped with everything you could possibly want and more for an extended stay. Flat screen tv plus additional tv in...
Featured review
Wonderful unit close to everything,easy in east out.Nice restaurants close to unit.Friendly atmosphere
Distance to beach: 6 miles to Lowdermilk beach and others
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Wide lake view single story home in the sought after community of Briarwood on a quiet cul de sac with sunny southern exposure looking at the lake. Open floor plan with high ceilings. Remodeled kitchen with granite counters. All new stainless steel appliances. Quiet dishwasher and refrigerator with...
Featured review
Briarwood Home is Close to everything in Naples. We have stayed downtown for years and renting a Home from Flynn's was painless. They were very helpful and organized in keeping us informed
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Available now for 2026 Off season and April 2027! Experience elevated beachfront living in this stunning 12th-floor, 2-bedroom, 2-bath condo at Barcelona in Vanderbilt Shores. Perfectly perched on Vanderbilt Beach, this modern coastal retreat features an open, sun-filled layout and elegant finishes throughout....
Distance to beach: 3 miles to Vanderbilt Beach/ Delano Wiggins State Park
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Welcome to your Happy Place that checks all the boxes! Three bedroom, 2 bathroom “Coach House” in the North Naples Gated Community of Carlton Lakes. It is one of the very few communities in Naples that allow tenants to have up to two pets of any size! It is also the perfect location to enjoy...
Featured review
Amazing Place, Exactly as pictured. From the moment you walk in you immediately notice the attention to detail. This place was clearly designed and decorated by a professional with style and comfort in...
Distance to beach: 2 miles to Clam's Pass
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Spend Winter in Naples, Not in TrafficImagine spending your mornings on a screened lanai overlooking the golf course, walking to Publix for groceries, enjoying an afternoon at the beach, and returning to a quiet, friendly community with resort-style amenities.This beautifully furnished first-floor...
Featured review
We had a wonderful stay in Turtle Lake Golf Colony in March/April 2026. The accommodations were lovely and location fantastic! Johan was very easy to work with and easy to contact with any issues that arose...
Distance to beach: 1 miles to Moorings Private Beach
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This first floor 2 bed, 2 bath condo is located in the heart of the Moorings neighborhood of Naples, just west of Route 41. Minutes to the Gulf of America and all downtown Naples has to offer. Everything is quickly accessible by foot, bike, or car, as well as sidewalks to the beach and Venetian Village....
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**Golf (excluding cart and green fees), pickle ball, tennis, bocce and access to all amenities (fitness center, clubhouse, restaurants, pools) with Membership Transfer. Lessons, clinics, and fitness class fees are additional. **30 day minimum stay required for all bookings**2nd floor luxury condo...
Distance to beach: 3 miles to Clam Pass Beach (through the mangrove forest!)
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Welcome to your stunning oasis in the heart of Naples! This 1st-floor condo has been completely remodeled and features brand-new furniture, offering a fresh, modern aesthetic that is ready for you to enjoy immediately.Highlights of the Home Full Remodel: Enjoy the peace of mind that comes with a...
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This luxurious fully renovated 2nd floor 2-bedroom lakefront coach home condo with cathedral ceilings and attached garage, is perfect for your escape to Naples. With 2 queen beds, 2 bathrooms, and amenities that include high speed internet and WiFi, large screen TV, gourmet kitchen with coffee station,...
Featured review
The condo is very clean and overlooks the pond, which made relaxing on the lanai enjoyable. We found the location to be excellent—tucked away from the traffic, yet conveniently close to the Mercato, Vanderbilt...
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Available from now until the end of January and from March 2025! Enjoy this stately, luxurious home with SUPERB WATER AND GOLF COURSE VIEWS! Comfortable designer furnishings, with 4 bedrooms plus Study and 4 full baths and one half bath. Beautiful travertine and hardwood flooring throughout, gourmet kitchen...
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SEASONAL RENTAL AVAILABLE. Enjoy a healthy and pristine living environment in our fully smoke-free condo. Off-Season rate for November 2025 and May 2026 through August 2026 is $2900 per month. December 2025 through April 2026 is offered at $5000 per month. Escape to paradise with this fabulous 2-Bedroom,...
Distance to beach: 8 miles to Vanderbilt Beach
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Beautiful seasonal rental including all new appliances located in lovely Quail Creek Village within an enchanting-gated community with the Country Club Lifestyle feel. An elegant escape with access to endless entertainment and a Golfer's Haven! Located on a cul-de-sac within easy to a small guest...
Distance to beach: 1 miles to Vanderbilt & Delnor-Wiggins Pass
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Beautifully remodeled privately owned home with brand new heated salt-water pool. We are beyond grateful not to have suffered any damage in the hurricanes. Located in beautiful, quiet Naples Park, and 1 mile to our beautiful sandy beaches at Delnor-Wiggins State Park and Vanderbilt beach.Fully furnished...
Featured review
We have stayed in Naples for 9 winters and this year was our favorite. Not only was Suraya, the owner extremely pleasant and easy to deal with, the house location, and beautifully decorated home was everything...
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Beautiful home, directly at the golf course, with a wonderful view, private pool, 3 bedrooms, 3 bathsWelcome to paradise !!!This beautiful villa is furnished in a modern and very tasteful way. Parquet in all rooms including bathrooms. The villa has 2 floors with 3 bedrooms (2 king size beds,...
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Located minutes from downtown Naples and the Beaches, this gorgeous condominium rental is perfectly located, along with luxurious amenities ensuring your Florida vacation experience is both exciting and relaxing.Stay in our comfortable and luxurious 2-bedroom condo while vacationing in beautiful Naples,...
Featured review
Great club amenities close by the unit and close to downtown. Pool, fitness center, tennis and shuttle to beach and downtown. Unit is clean and well maintained.
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First floor apartment overlooking the lake and fountain at the 17th fairway of beautiful Cypress Woods Golf & Country Club Course this property is fully furnished with complete amenities, big screen TV, Sonos sound system and a lot more.It is available for seasonal 3 or 4 month rental. A 10...
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THIS BEAUTIFUL ONE BEDROOM CONDO IS A FIRST FLOOR UNIT WITH COVERED PARKING. THIS CONDO WAS RECENTLY RENOVATED AND HAS NEW OPEN FLOOR PLAN WITH DINING AREA, LIVING AREA AND KITCHEN WITH BAR AREA. A 75 INCH SAMSUNG TV WITH COMCAST SERVICE AND INTERNETNCLUDED.THIS KITCHEN IS FULLY STOCKED WITH DISHES, GLASSES...
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Welcome to your perfect retreat at the Glades Resort in Naples, Florida! This newly renovated, 1600-square-foot condo is set on two of the resort’s pristine golf courses, offering direct access to green fairways and scenic views. The 3-bedroom condo is also just steps away from one of the resort’s...
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Hello! Welcome to your Happy Place. We know you will love it here and make some fantastic memories to take home with you. We are 5 blocks from Vanderbilt Beach and just minutes from Delnor-Wiggins State Park. This is a Dog-friendly home.The outside patio is completely screened and is perfect for...
Featured review
It was really acute house. Clean and located in a mazing area by everything.If we plan on going back to Glorida we would rent again and it’s dog friendly.
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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
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Welcome to your bright and cheerful Naples retreat! This fully furnished 2-bedroom, 2-bath end-unit condo is tucked away on a peaceful cul-de-sac in the desirable Spoonbill community. Just steps from the private pool and spa, this serene second-floor condo offers wraparound views of sparkling lakes and...
Featured review
We are delighted with this two-month rental. Entry was easy, place very attractive and clean. Well stocked with sheets, towels, blankets, kitchen and cleaning tools. Lovely lake views, quiet and private...
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Come and enjoy this private retreat in the wonderful and friendly gated community of Tarpon Cove (Martinique Condo). This 1400 square foot condo is an end unit with three bedrooms and two bathrooms on the first floor with lake and preserve views. In the complex itself, there are three pools, a Jacuzzi...
Featured review
Absolutely beautiful condo and property...Everything advertised by owner was as stated...the owners wanted to make our stay as comfortable as possible...instructions provided on everything was complete...the...
Distance to beach: 5 miles to Vanderbilt Beach
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Immerse yourself in luxury in this beautiful single-family pool home perfectly situated overlooking the stunning 18-hole golf course at Stonebridge Country Club. Enjoy the privacy of your own heated pool and extended lanai/backyard as you watch the sun set over the lush greens.Rental offers full...
Featured review
Just coming to the end of a ten week stay at this property, everything was 5 star. House very comfortable and very well equipped with everything you could possibly need. Great pool area, very private, all...
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Private 3BR/2BA Retreat in Gated Naples Community – 6 Miles from BeachesUnwind in this bright and spacious 3-bedroom, 2-bathroom home located in a quiet gated community, just minutes from Naples' world-famous beaches. Enjoy an open living and dining area, fully equipped kitchen, and peaceful...
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2BR/2BA condo in Naples, FL – 30-day minimum stay. Enjoy sunset views from the lanai, a fully equipped kitchen, Wi-Fi, smart TVs with streaming capabilities, and beach gear included. Community amenities: pool, pickle-ball, and tennis. 4 miles from Marco Island and 14 miles from 5th Ave in Naples....
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Stunning contemporary home on the beach with breaktaking views of the Gulf of Mexico throughout the home. Four bedroom, four bath home is bathed in sunlight and offers "front row" beach and Gulf views from many vantage points, with incredible sights and sounds of the Gulf. The home has in...
Featured review
Beautiful view all through out. Great home with en-suite bedrooms. Directly on the beach, doesn’t get better than this. The realtor was very helpful and accommodating. The entire experience was great....
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Beautiful lakefront end unit on the first floor. The master bedroom has a king sized bed. Second bedroom has two twin beds. Entire condo has been painted in December 2020. Kitchen renovation completed in January 2021. The amenities include wifi, cable tv, washer and dryer. Community has a large heated...
Featured review
We stayed at Marco’s condo for six weeks and had a fantastic time. Upon arrival we found the condo in spotless condition. Normally when we rent we always need to do some cleaning but not in this case....
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This Meadowood Townhome is fully furnished and turnkey with quartz countertops, stainless steel appliances and an open kitchen-living room layout. The gated community includes a beautiful clubhouse, fitness center, pool and basketball court. Located close by to several new shopping plazas, interstate...
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1st floor condo in a great Naples central location and quiet community of the Fairways at Emerald Greens. All the attractions of the beach, Mercato and 5th Ave are all within a 10-15 minute drive. You also have plenty of shopping and dining within walking distance as well. The Fairways has a heated pool...
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FOUNTAINS I in Naples.Fully FURNISHED TURNKEY FIRST FLOOR condo with carport AVAILABLE May until the end of November 2027 for only $1500 a month (December is $3500). 2027 season (Jan - Apr) at $4500/month. Beautifully REMODELED and furnished 2 bedrooms, 2 baths with gorgeous LAKE VIEW. All new gorgeous...
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We are offering our elegant and spacious, fully furnished 2 bedroom, 2 bathroom Villa located on a lovely private Naples community of Walden Oaks. Entering the charming “Walden Oaks” community you will come across the large lake with an Island heated-pool, bordered by tall and lovely palm...
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Nestled within the private and guarded gates of prestigious Treviso Bay, this 2 Bedroom, 2 Bathroom 'BELLINI' model in ACQUA COURT is on the 3rd Floor (w/elevator). A private balcony provides a front row seat for serene views of the Rookery Bay National Estuarine Research Reserve. It is fully...
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Turnkey, 3 bedroom, 2 bath condo. It is located in the heart of Naples within a 15 minute drive to Mercato, 15 minutes to Fifth Avenue and 10 minutes to the beach. The Fairways at Emerald Greens is a quiet, friendly community with tennis courts, pickleball courts, a heated pool, hot tub and clubhouse....
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This stunning luxury villa is a private pool home overlooking a large lake boasting many luxury amenities. Located in Naples Florida, a gated community of single-family homes featuring award-winning designs. Situated within a few minutes of downtown Naples and its pristine white sand beaches and local...
Distance to beach: 3 miles to Delnor Wiggins
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An ideally located condo in North Naples, west of 41 and a short drive to Vanderbilt Beach, Delnor Wiggins State Park, and Barefoot Beach.The unit includes 3 bedrooms and 2 bathrooms and can accommodate six people. The Master contains a queen bed. The second bedroom has 2 twin beds. The Den/third...
Featured review
Loved staying here. Nice location overlooking a pond. Very close to the lakehouse (workout facility). Also close to the front gate which we appreciated. Easier to get to Charleston and Fresh Market shopping...
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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