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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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Beautify fully furnished condo in Pelican Bay! Great second floor unit in St. Simone with 3 bedrooms plus den, 2 full baths (dual sinks and jetted bathtub in the master). walk in closets and extra storage room. Completely remodeled with an enclosed lanai, new kitchen cabinets, new quartz countertops in...
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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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Welcome to your ultimate beach getaway in our brand-new, stunning beach house. Just a leisurely bike ride or walk from Vanderbilt Beach and the Mercato, this location perfectly marries convenience and tranquility.Our 4-bedroom, 3-bathroom residence is designed with an emphasis on leisure and comfort....
Featured review
The house was good thank you for the rental we will return Mr&Mrs Furbay Maryland thanks again for making our 35th anniversary very special and relaxing
Distance to beach: 7 miles to Naples
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Comfortable 1600 sq.ft 3 bedroom 2 bath condo located in Lely Naples. King in master, Queen in guest room with queen sleeper sofa in the den.Turn key furnished just bring your toothbrush.Kitchen and baths total redo in 2025Quite non-gated community. Lanai area has beautiful first floor view...
Featured review
Very nice, comfortable condo. Condo had everything we needed. Pool perfect. Neighbor all very friendly. Close by Marco Island, beaches and downtown Napkes. Tom was a wonderful host!
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This beautifully renovated condo offers a Paradise Experience. The condo has a King Size in Master and King size in Guest Room (or TWO Twins - please specify )This sunny and cheerful condo overlooks the tropical gardens. . Washer and Dryer in unit. Freshly painted and new furnishings make this 1st...
Featured review
My husband & I have been renting properties from VRBO, Airbnb & private owners for many years and for the most part, rentals have met our expectations, but none like this one. This rental definitely exceeded...
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This is a wonderful first floor ranch-style villa with a open and split bedroom floor plan and 1,503 SF of living space. The condo consists of two bedrooms, two full bathrooms, an office / den, large living room, a lanai facing one of the two community lakes and a two-car garage.The main entry door...
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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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Welcome to paradise at the prestigious Lely Ole community in beautiful Naples, Florida. This stunning 2-bedroom, 2.5 bath luxury home situated on a private quad offers a spacious open floor plan with abundant natural light, modern gourmet kitchen and an elegant master suite.The perfect blend of modern...
Featured review
We had an excellent stay this October. The home was incredibly clean and well-kept, the host was extremely responsive and communicated clearly from start to finish, making the entire process smooth and...
Distance to beach: 5 miles to Delnor-Wiggins Pass State Park
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AVAILABLE FOR SEASONAL AND LONG-TERM RENT:April 2026 $5,800 May-Oct 2026 $3,600 Nov 2026 $5,000 Dec 2026 $6,000 Jan-Mar 2027 $10,000 ask about other months annual $4,200/mo11% Florida Tourist Tax is extra for rentals less than 6 months. 2 months term or longer is preferred. ASK FOR SPECIAL...
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Distance to beach: 6 miles to Tiger Tail Beach
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This brand new second floor condo is the Montserrat model, which is the largest floor plan in the community. It features 3 bedrooms, an open floor plan and a loft area that can be an additional work, study or play area. Pets are permitted with prior approval and an additional fee.The condo consists...
Distance to beach: 900 feet to One block to Lowdermilk Beach
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Ready to soak in the best of Naples? This highly sought‑after property is open for select summer and fall months in 2026—book early for this popular season!Located just one block from pristine Lowdermilk Beach and the brand‑new Four Seasons hotel, restaurants and shopping, this beautifully...
Featured review
From the moment we arrived at the condo at Coquina Cove we felt right at home. The condo was beautifully set up with everything you could possibly want or need during your stay. The host Elise was great...
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Welcome to Modern Paradise! Ideally situated just minutes from the vibrant shops, restaurants, and beach of 5th Avenue. This elegant two-story residence boasts 5 spacious bedrooms, exuding sophistication and comfort. Enjoy sunny days by the heated pool or take a leisurely nap in the hammock and enjoy...
Featured review
We had such a great time with family as we visited the Naples area. Kids loved Naples and even Bonita as they really blend together. Our contacts from the management company were wonderful and always available!...
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This brand new second floor condo, a West Indies Style Architecture completed in 2024 will impress as it features ceramic tile flooring throughout, beautiful appointed cabinetry and a neutral color palette.The condo consists of 2,010 SF total, one-car garage, a large master bedroom ensuite with an...
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Your Naples season, done right. This furnished 3-bedroom, 2.5-bath Park Shore vacation rental sits on a quiet, winding street overlooking Swan Lake — with a private pool, sun-drenched southern exposure, and the beach, Venetian Village, and Waterside Shops all just minutes away.The Residence Nearly...
Featured review
Nice house, while not on the gulf it was a good location to get to 5th Avenue for nice shopping and restaurants. The water view is a small pond that had some ducks. Newly remodeled it appears. Neighbors...
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Unwind in this bright and spacious 3-bedroom, 2 & 1/2-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 surroundings. We are renting our home as a seasonal rental with a...
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Nestled within the exclusive Treviso Bay community, this elegant 2-bedroom, 2-bathroom condo epitomizes luxury living in Naples. Designed with sophistication and comfort in mind, the unit is finely furnished, offering residents a taste of upscale living within a gated enclave. The centerpiece of Treviso...
Featured review
Our stay in Treviso Bay was absolutely perfect! The community is stunning, with beautifully maintained grounds and a welcoming atmosphere. The pool was incredible—like something out of a luxury resort!...
Distance to beach: 1 miles to Vanderbilt Beach
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This comfortable spacious luxury villa was built in 2014, generously equipped with modern and high quality furnishings. The equipment offers optimal living quality.The floor plan of the house and the pool area gives you a very good impression of the generosity. In total, the house has 4 bedrooms with...
Featured review
We absolutely loved our stay at this vacation rental! The house was open, airy, and incredibly spacious—perfect for relaxing and spending quality time together. Everything was spotless when we arrived,...
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Situated 15 minutes from downtown and Naples Beach, 15 minutes from Marco Island and 5 minutes from numerous golf courses. This 1 year old decorator furnished 2BD/2BR with den villa is available from November through April. This Villa sleeps 6 with a king pullout in den. Expansive kitchen with breakfast...
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Welcome to your slice of paradise! This bright and beautifully maintained 2-bedroom, 2-bath retreat offers the perfect blend of comfort, style, and location. Enjoy morning coffee or evening cocktails by the private pool with a nature view, then head out to explore- you’re just minutes from Naples’...
Featured review
Perfect stay! Would book over and over again! My family enjoyed the house and the location is great!!! The owner is very helpful and accommodating. We will be back!
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This multiplex condo, a West Indies Style Architecture completed in 2022 will impress as it features ceramic tile flooring in the main areas and carpet in the bedrooms, beautiful appointed cabinetry and a beach-driven color palette. There is an elevator and parking located underneath the building. This...
Distance to beach: 5 miles to Vanderbilt Beach & Wiggins Pass State Park
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This beautifully renovated home features first floor master with large soaking tub and double vanity, The open floor plan leads to the stunning oversized lanai and hot tub to watch the amazing sunsets and golf course views. The newly paved lanai has so much privacy with outdoor kitchen for entertaining....
Featured review
The home was immaculate. The owner did so many small things that made our stay special. The view of the course from the lania was awesome. The golf course was short, but tough. Overall a great experience.
Distance to beach: 50 yards to 5TH AVENUE BEACH
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TWO BEDROOMS EACH HAVE A KING BED ,MULTIPLE DRESSERS AND AMPLE CLOSET SPACE TWO FULL BATHROOMS EACH CONTAINING A SHOWER AND TUB COMBINATION GROUND LEVEL PRIVATE OUTDOOR PATIO WITH BEAUTIFUL ORCHID GARDEN OVERLOOKING 5TH AVENUE LARGE OPEN LIVING DINING AREA LARGE FULL KITCHEN WITH A LARGE NUMBER OF...
Featured review
Very nice, spacious condo, as advertised. Excellent position near to the beach and restaurants. Perfect for a couple. Randy and Amy were great hosts, very helpful, an easy check in. Would highly recommend....
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Discover coastal living at its finest in this stunning two bedroom , two bath condo with den/office for rent on Vanderbilt beach in Naples, Florida. The master bedroom has a king bed with a Gulf view and en-suite bathroom. The second/guest bedroom has a queen bed and an en-suite bathroom for guest...
Featured review
Our stay at this condo was amazing from start to finish. If you’re looking for the perfect blend of luxury, comfort, and location, look no further! The condo itself was beautifully decorated with a sophisticated...
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Some places you visit. Old Naples, you fall for — and there's no better place to fall from than the doorstep of 850 Central, a boutique enclave of just 22 residences on the corner of 8th Street and Central Avenue, where the buzz of downtown meets the calm of the Gulf. This isn't a high-rise...
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Enjoy the privacy and comfort of this elegant 3 bedroom / 3 full bathroom family home on the 6th hole of the pristine Vanderbilt Country Club.This beautiful home is located within Vanderbilt Country Club on the sixth hole of the golf course with a one-of-a-kind amazing view of the lake. Situated on...
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Lakefront luxury living with a screened pool & spa in Stock Development's premier Naples community. Set on a serene lake in the heart of Naples, this single-story luxury home blends an open, light-filled great room with a chef's kitchen, spacious bedrooms, and a screened lanai built for...
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Welcome to your Naples escape on Marlin Drive! This beautifully updated single-family home is perfectly situated on the water in the highly desirable Royal Harbor community. Offering 3 spacious bedrooms plus a versatile den with a sleeper sofa, this residence combines comfort with the ultimate waterfront...
Distance to beach: 4 miles to Tiger Tail
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multiplex condo with amazing lake viewThis brand new multiplex condo, a West Indies Style Architecture completed in 2021 will impress as it features ceramic tile flooring throughout, beautiful appointed cabinetry and a beach-driven color palette. There is an elevator and parking located underneath...
Distance to beach: 1 miles to Vanderbilt Beach
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MAR and APR 2026 are NOW available! 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 – CLOSE TO BEACH...
Featured review
We started out the month with a few problems at the house. AC compressor went out, ice machine was broken, and pool heat had to be turned off. Shane was excellent to work with, getting everything taken...
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first floor classic coach home with secluded garden viewThis wonderful first floor condo, a West Indies Style Architecture will impress as it features ceramic tile flooring throughout, beautiful appointed cabinetry and a beach-driven color palette. Pets are permitted with prior approval, an additional...
Featured review
A lovely condo in East Naples Florida. Close to the beach, nice restaurants,and shopping. Peaceful location and setting.with lake view and peaceful fountains. Beautiful sunsets from the lanai. A gorgeous...
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Welcome to The Pier House, an Old Naples masterpiece where timeless coastal style meets top-tier finishes. With just over 5,200 square feet and a resort-style courtyard pool, the home lives like a private sanctuary—perfect for long, lazy beach days and golden-hour strolls to the Naples Pier for...
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Summary! Coastal Naples getaway in the popular Bayshore Arts District! New (2020), modern home stocked for families. Enjoy private saltwater pool/spa, outdoor shower, large screened lanai. Close to pickleball & Celebration Park. Bring your boat! This property is 5 minutes to Bayshore Boat Launch....
Distance to beach: 10 miles to Naples Beach
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Excellent location in #1 rated luxury Lely Resort in beautiful Naples!Taste fully decorated furnished home with your own private pool and spa located in the gated community of Caldecott in Lely resort! Rated the #1 community in Naples where you can experience the amenities of a luxury clubhouse with...
Featured review
This is a wonderful home with a great location within Lely resort. The home is well maintained with everything you need for a winter seasonal rental. Fully stocked kitchen, and all the chairs, towels and...
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Welcome to this exquisite 3-bedroom, 2-bathroom home in the sought-after Naples Reserve community. At $8,500/month in season, experience resort-style living at its finest with an array of exceptional amenities to enhance your stay. Step outside and immerse yourself in the resort-style pool, perfect for...
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Summary: 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, Bolero is your ideal home away from home. This newly updated home is ready for...
Distance to beach: 3 miles to Delnor-Wiggins Pass State Park
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NEW LISTING! Coastal elegance meets lakeside living at Casa Burano — a beautifully appointed two-bedroom, two-bathroom ground-floor condo opening its door this season in the heart of North Naples.Inside Step inside Casa Burano and you’ll find a thoughtfully designed space that feels...
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There are 2 bedrooms with 2 full bathrooms with a designated parking space. One bedroom has a king-size bed with a TV and the other has two twin very comfortable beds. No pets allowed and ideal for a couple. Preferable for 60 days during winter months (Jan- Feb- March).The condo is fully equipped...
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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Welcome to an exquisite abode at 380 4th Avenue South, Unit 380, nestled in the heart of scenic Naples, FL. This tastefully appointed residence offers 1,000 square feet of thoughtfully designed living space. Delight in two elegantly crafted bedrooms and two pristine bathrooms, all enhanced by central...
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second floor beautifully appointed classic coach homeThis new second floor condo will impress as it features all laminate wood flooring throughout, beautifully appointed cabinetry and a beach driven light-and-bright color palette.The condo consists of 1,988 SF total, one-car garage, a large master...
Distance to beach: 17 miles to South Beach, Marco Island
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Gorgeous wide water views and easy water access from this very private, 2300 sq. ft. furnished retreat w/ private elevator! This fantastic location affords the ability to stay at home and chill or easily set out for more adventure by land or sea via a provided dock!Marco Island and their stunning...
Featured review
This condo was fabulous. 3 beds and 3 baths afforded plenty of room for friends and guest , winter 2025. The pool was always ready for a sunny afternoon. A drink on your private lanai watching the manatees...
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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: 2 miles to Closest to Delnor Wiggins, Vanderbilt and Bonita
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This beautifully decorated newly remodeled first floor unit has a glass/screen enclosed lanai with a scenic views overlooking the natural preserve. Just steps away from our condo are the tennis/pickleball court and pool areas. This charming condo is conveniently located West of 41 in North Naples, just...
Featured review
Everything about our experience was wonderful. Gail is the nicest and most easiest person to work with. Condo has everything you need, beautifully decorated and comfortable. Area is close to beaches,...
Distance to beach: 2 miles to Fifth Avenue Beach
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This oversized condo is like no other. Completely remodeled with lots of customized features. Beautiful whitewash wood floors, beautiful white gray and blue palette makes this condo feel light and peaceful. A complete new kitchen with white quartz and lacquer cabinets makes cooking a joy. The 12’...
Featured review
Myself and my family stayed at the Naples Bay Cottages (Naples Bay Resort and Club) for 7 nights towards the end of July 2026. This is the second time we have stayed at this property and enjoy it so much...
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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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Beautiful, modern 3 bedroom and 2 full bathroom house, located in North Naples with a back yard that backs up to the woods which provides the utmost privacy.Walking into the home, you will enter an open living space boasting a modern equipped full kitchen. Reverse Osmosis System (Portable water)Outside,...
Featured review
I stayed in Naples for 2 nights and 3 days, and I loved it. It’s a very peaceful city, the beaches are close by (about 25 minutes), Baker Park is beautiful, and 5th Avenue is great for restaurants. I...
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s - A beach volleyball court - Basketball facilities - A playground - Two communal pools in the esteemed Briarwood Community- Convenience:A fully equipped laundry room with washer and dryer for your comfort.This villa isn't just a place to stay; it's a destination where luxury, privacy,...
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Castleton Gardens is a highly sought after gated condo community situated in central Olde Naples, walking distance from Gulf beaches, restaurants, and shops.This prime location is exceptional and ideal for a Southwest Florida getaway. This ground floor condo offers high-end finishings and convenience....
Featured review
We had an amazing vacation,the condo and location were perfect. The condo was beautiful and had everything you could need,grounds were wonderful lovely pool and hot tub.Location was great too walkable to...
Distance to beach: 6 miles to Naples beach (close to downtown)
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This beautiful 3 BD condo is located in the Magnolia Falls area of the gated community of Falling Waters. This condo, on the 2nd floor, is great for viewing the beautiful lake from the lanai. The unit is an end unit providing additional privacy. The large 1573 sq ft. unit features a master bedroom...
Featured review
We stayed here for the month of April. The condo is very comfortable, spacious, with a nice view of the pond with a fountain. The lanai was great, at the end of the day, to enjoy the view. The pool was...
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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