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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.
Distance to beach: 8 miles to Marco Island
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Great Location, this home has a two-car garage, private patio, three bedrooms and 2.5 baths. This casita has all you need to have a relaxing vacation. Laundry room, master bedroom and master bath are all other bedrooms including laundry room are on the second floor, and all living space on the first floor,...
Distance to beach: 3 miles to The Naples Beach and Pier
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This is a top floor condo with soaring cathedral ceilings and some of the best views in the community. The cathedral ceilings in the living room, dining room, sitting room and kitchen add a lot to the feeling of openness you get when you walk through the door. You will love the wide open views from your...
Featured review
We had a wonderful 3-month stay in this ideally located, quiet, 3rd floor condo that overlooks a 7th green and beautiful water view. The accommodation is very clean, has a well-equipped kitchen, and new...
Distance to beach: 6 miles to Vanderbilt Beach
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2br, 2 full bath. Queen bed, lanai with water feature view. All updated, large tvs in living room and main bedroom. Short drive to Vanderbilt beach, 41 and easy highway access, great location. Across from Seed to Table in North Naples. Credit/background check required. Condo updated and in great shape....
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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...
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 condo has nice lake and fountain views from this spacious second-floor end unit condo. This condo has both a front lanai and a rear lanai which is nice for enjoying the outdoors and cross breezes in the condo. Enjoy the spacious living area with 1349 square feet, 2 bedrooms, 2 bathrooms, large laundry...
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Welcome to your home away from home in beautiful Naples, Florida! This bright and spacious 2-bedroom, 2-bathroom second-floor end-unit condo is located in a peaceful 55+, resort-feel community, overlooking the lush fairways of the Quail Run Golf Course.Enjoy Florida living at its finest with a sunny...
Featured review
What a lovely condo and Peg was great to deal with. The condo is spacious and well stocked. Very comfortable. Great location, the pool, bbq and tennis courts are just a short walk. We thoroughly enjoyed...
Distance to beach: 100 yards to Vanderbilt Beach
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Life is Good at The REGATTA! One Block to Naples Pristine Beach with a Great View at just $14,000/month in season! Naples Florida is ranked among the Top 10 Florida vacation destinations by US NEWS & WORLD REPORT! Luxury 3BD/3BA with a spectacular panoramic water view is the perfect vacation rental...
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Step into luxury at $22,000/month in-season in this stunning 9th-floor residence in the Grande Geneva at The Dunes of Naples. Enjoy panoramic Gulf views, serene mangroves, and spectacular sunsets from your expansive lanai. This beautifully furnished condo features 3 bedrooms and 3 full bathrooms, with...
Distance to beach: 5 miles to Barefoot Beach / Delnor Wiggins State Park
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Where serenity meets luxury in Pelican Bay at $15,000/month in season—welcome to Breakwater. This updated end-unit residence offers a bright, open floor plan with a modern color palette and stylish furnishings. Featuring 3 bedrooms and 2.5 baths, the home is filled with natural light and offers...
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There is no better place to be during the winter than enjoying the warm weather and taking in the bright Southwest Florida sun in Pelican Bay.This property offers a unusual two car attached garage and the privacy, independence and security of a single family home. You can avoid the elevators and...
Featured review
This condo is as beautiful as the pictures suggest, which is not always the case. It is open and airy and is beautifully decorated.It is super well stocked and has everything you need for a fabulous vacation....
Distance to beach: 6 miles to Naples Pier and Vanderbilt
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Gorgeous hotel style suites. Penthouse, corner suite. This condo is suitable for one couple or a single person. You wont be disappointed. Best King size mattresses you'll ever sleep on. It's like sleeping on a cloud... What are you waiting for... contact us or book. It won't last! 2...
Featured review
Positano Place is a gated, safe and quiet community. The condo has two spacious bedrooms with new mattresses that ensure a restful sleep. The furnishings are very comfortable. Two spacious bathrooms. The...
Distance to beach: 1 miles to Vanderbilt Beach
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LOCATED ON THE WIDEST CANAL IN CONNERS OF VANDERBILT BEACH, WITH AMAZING VIEWS FROM (liv, dining, kitchen, main bedroom and family room) - Resort style living for your winter vacation in Naples. Be ready to enjoy every amenity and all the attractions nearby.AMAZING OUTDOORS: Three terraced outdoor...
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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...
Featured review
This house is the Perfect Location!!! 13 minute walk to the beach. The pool was new and we enjoyed it everyday! Meredith at the rental agency was super quick with responses. The beach umbrella in the garage...
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New and Renovated home with all new furniture 2 large living rooms TV and Internet 4 bedrooms with 6 beds A huge swimming pool and outdoor furniture Full kitchen Laundry Garage for vehicle parking Clubhouse close with a swimming pool, hot tub, and fitness center Close to Dunkin Donuts,...
Distance to beach: 10 yards to Moorings Beach
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Experience waterfront living at $10,500/month in-season with ever-changing views of beautiful Moorings Bay! This light-filled, third-floor end unit offers approximately 1,400 square feet of living space with two bedrooms and two bathrooms. Beautifully remodeled with an open floor plan and a soft, neutral...
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Beautifully furnished coastal condo in Heritage Bay! Your tropical, golf, getaway is awaiting your arrival. Two bedrooms, and 2 bathrooms and set up with 1 queen bed and 2 twin beds to accommodate your guests. Relax on your lanai with both golf and lake view and take in the breathtaking southwest Florida...
Featured review
We enjoyed our stay in Heritage bay ,the condo was good and Sara made everything super easy for us hope to rent again in the future.
Distance to beach: 1 miles to Vanderbilt & Delnor Wiggins
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This exceptional terrace unit in the Grande Geneva is one-of-a-kind, boasting the largest private deck in the building with its very own private spa and outdoor kitchen at just $22,500/month in-season. Spanning the entire side of the building and exclusive to this unit, the terrace is perfect for entertaining...
Distance to beach: 1 miles to Vanderbilt
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MAR 5th & APR 2027 available! We also have other homes available in 2027. Call Shane or inquire for details.ALL INCLUSIVE monthly rate May to Dec 19th $6,775. Dec 20th to Apr $9,880 (rent, tax, cleaning, utilities, cable/wifi, damage waiver, etc. all included). Naples FL turnkey vacation rental.LARGE...
Featured review
Great property. Shane was excellent. We would stay again. We love Naples. Pool and hot tub worked great
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Beautiful fully renovated 2 bedroom 2 bath apartment in Heritage Bay community. Rental comes with full access to 27 hole golf course on property as well as all amenities in the complex such as the pool, tennis, bocce, bike trails among others!!We also have another similar condo in the community (2...
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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: 2 miles to Clam Pass Beach is approximately 2.5 miles
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Golf Condo by the Sea – So Close to the Beach!Welcome to Golf Condo by the Sea, located in the desirable Mira Vista Condominium Community overlooking the beautiful Quail Run Golf Course.Please Note: We also own a beautifully updated 4th-floor condo in this same building. See Listing #12283...
Featured review
This centrally located condo has all the convenience you can imagine, the pool is a few steps away, the beach is a short drive. Shopping, dining and entertainment is all within a short drive away. The condo...
Distance to beach: 6 miles to Clam Pass
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Forest Lakes Naples Condo 55 and over: Live the quintessential Naples lifestyle in this beautifully renovated 2-bedroom, 2-bathroom condo. Just minutes from Naples’ top dining, shopping, parks, and beaches — this is location and lifestyle. This exceptional first floor unit presents an incredible...
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BRIGHT 2 BEDROOM, 2 BATHROOM CONDO ON THE GROUND FLOOR WITH WALKOUT PATIO. THE ENCLAVE AT NAPLES IS LOCATED 10 MINUTES FROM BEAUTIFUL DOWNTOWN NAPLES, 5TH AVENUE, WHITE SAND BEACHES, PLENTY OF SHOPPING, DINING, GOLFING, FISHING AND BOATING CLOSE BY. RESORT STYLE POOL AREA WITH GYM, BILLIARDS ROOM, RACQUETBALL,...
Distance to beach: 17 miles to Marco Island Beach
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Near the Ocean!! Screened back porch water view to enjoy beautiful sunsets! 2bed/2bath condo offers kitchen with lots of cabinet space with tile floor, laminate wood flooring in the living areas and carpet in the bedrooms. Washer and dryer included. One car garage and boat dock/lift behind apartment.Wireless...
Featured review
We had the opportunity to rent this condo for January and February, 2026. Our hostess Lymari is the sweetest person to deal with. She went out of her way to make our stay there as carefree as possible....
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Welcome to Tamarindo, South Naples' newest and most exclusive gated community. This stunning rental property offers the highly sought-after Clifton floor plan, featuring 3 spacious and elegantly furnished bedrooms and 2 luxurious full bathrooms as well as your own private pool, your very own screened-in...
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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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Welcome to your BEAUTIFULLY renovated home away from home! ENJOY brand-new furnishings and designer coastal decor. This light and bright home feels extra spacious thanks to soaring ceilings and an abundance of windows. Enjoy stunning water views, offering a birdwatcher's paradise with delightful...
Featured review
We spent the month of October here and it was perfect for what we needed. It was close to all types of shopping and many restaurants. The renovation was well done and it was very well equipped and supplied...
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Lanai: Get Lazy on the couch or enjoy a bite at the table...the view is always outstanding.! On a cool night, curl up under a cozy blanket; read or just enjoy the view and fresh air.Master Bedroom: Tuck into the King size 4 post bed and watch TV, stream your favorite movie, use the stable internet...
Featured review
Très bien situé,près de la plage et du centre ville de Naples. Condo bien équipé et très confortable. Les propriétaires sont charmants et disponibles. Nous recommandons cet endroit à 100%
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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...
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Fully Furnished/Turnkey: LELY GOLF ESTATES stunning corner lot residence featuring three (3) bedrooms, two (2) bathrooms, and a two (2) car garage with a pool, now available for immediate occupancy. The property features a fully equipped kitchen, a dining area accommodating eight individuals, and a living...
Featured review
We greatly enjoyed our stay in February 2026. Very spacious and nicely furnished. The pool and outside area by the pool is awesome! The heated pool was nice and came in handy on the cooler days. Plenty...
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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Stunning seasonal condo for rent beginning December 1, 2026 to April 30, 2027. Third story condo with elevator is located in Lely which is near the beautiful Naples beaches and popular restaurant’s and shops along 5th Avenue. The newly renovated 2 bedroom 2 bath condo features a king bed in the...
Featured review
The condo was beautiful! A hidden gem. Owner was a super host. Close to shopping and a few restaurants.
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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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Absolutely stunning 2 bedroom, 2 full bathroom condo at Carlton Lakes one of the most beautiful resort developments in Naples. This unit is located on the first floor of a 2 story condo. The condo is tastefully decorated with brand new furnishings and has a wraparound screened lanai. Open floor plan with...
Featured review
5 star rental and a Great Find in a beautiful part of Naples Florida .The owner was an extremely accommodating host for all of our needs . The additional extras to this property were an area pool ,,community...
Distance to beach: 4 miles to Vanderbilt
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Stay for a season or live at the heart of North Naples’ most coveted lifestyle destination — where world-class dining, boutique shopping, and entertainment are literally at your doorstep. This elegant, fully furnished 1,500 sq ft residence at Mercato places you in one of Southwest Florida’s...
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What a view! Beautiful second floor unit at Huntington Lakes, a gated community in North Naples. Just a few minutes away from top-rated restaurants, shopping and the beach.This fully furnished unit comes with everything you need for a comfortable and convenient stay. It has been completely updated...
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TCompletely renovated first floor garden condo. two bedroom two bath 1420 sq. Ft. Turn key furnished, one block from the beach Features an open concept, Floor Plan, and a brand new state of the art kitchen with all new appliances, cabinetry, and finishes. The light filled living room offers an inviting...
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 for the 2027 Season * Relax and unwind in this bright, spacious 2 bedroom 2 bath getaway. Featuring 2 king beds and a pull out couch for additional guests. Enjoy stunning waterfront views through the large picture window, or take a short stroll to the private beach access. Cool off in the pool...
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Available March, and April! Welcome to your luxurious downtown retreat! This exquisite residence is nestled within the esteemed 780 Fifth luxury condominiums and showcases an expansive open floor plan, featuring a recently updated kitchen with modern cabinetry, quartz countertops, a chic bar area, two...
Distance to beach: 2 miles to Delnor-Wiggins Pass State Park
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January 2027 open - ask for a quote.Our home is stocked with everything you need for the beach, the pool, eating in, going out, or playing games!Welcome to Slow M'Ocean Naples for your sunny Florida Vacation, a relaxed and well-appointed Naples Park retreat designed for easy beach living...
Featured review
We only had a week but thoroughly enjoy our time. The house was well maintained and the heated pool was a bonus. Lots of extras for beach time.
Distance to beach: 4 miles to Naples Pier Beach
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Quiet Oasis Naples – Your Relaxing Florida GetawayWelcome to Quiet Oasis Naples, your perfect home away from home in beautiful Naples, Florida. This romantic and peaceful condo offers the ideal blend of comfort, convenience, and coastal charm — perfect for couples, families, snowbirds,...
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Just reduced to $3000 a month in season - Available for the full 2026 season or off-season, this turnkey-furnished 2-bedroom, 2-bath corner unit is move-in ready and beautifully updated. Enjoy brand-new, comfortable furnishings, new luxury vinyl plank flooring, and new appliances, along with updated bathrooms—all...
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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 Happy Place that checks all the boxes! Three bedroom, 2 bathroom “Coach House” in the North Naples Gated Community of Carlton Lakes - the Best Spot in Naples! It is one of the few areas in Naples that allow tenants to have UP TO TWO PETS ANY SIZE! We have TWO OTHER nearly...
Featured review
I stayed at this location with my wife in December for 3.5 weeks and we miss it already, great location and pet friendly. Super friendly neighbors and a safe gated community. Walking distance to Seed To...
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.
Distance to beach: 4 miles to Delano Wiggins Park
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We also have THREE virtually identical units that are EXTREMELY PET FRIENDLY at a neighboring gated community with loads of amenities where we can allow up to TWO PETS ANY SIZE! Please call us at two three nine five nine five nine one six zero.Welcome to your Happy Place that checks all the boxes!...
Featured review
We rented this property from May till October. It has a great location and close to everything!! Grocery stores, Walmart, Sam’s Club. Great places to grab breakfast, lunch and dinner. Downtown Naples...
Distance to beach: 6 miles to Naples beach
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Lely golf estate condo, second floor Unit Big Lanai with a beautiful view to the pool. 1 covered parking spot Masterbedroom with big app tv . We have a Amazon fire tv stick but you can also bring your own. bathroom and walkin closet Nice and quiet neighborhoodPS : the pin on the map show that...
Featured review
Perfect location between Naples and Marco Island! Easy drive to all the popular spots. The condo felt like home, very comfortable! The pool was awesome and only a few steps away! I would highly recommend...
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Currently available Jan-Mar 2027! All rentals begin on 1st of month. Enjoy the best of Naples living in this beautifully updated, completely turnkey, and exceptionally clean 1,350 sq. ft. first-floor condo! With an open floor plan and abundant natural light, this inviting home offers the perfect blend...
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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