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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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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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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
My family and I stayed at this lovely house in a perfect area. It was a 15 minute drive to either Naples or Marco Island. The house was clean and offered plenty of space for my family, which includes...
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Enjoy a relaxing experience at this centrally located first floor condo with a golf course view in Naples Florida- only 10 minutes from the Clam Pass Beach and I-75, and only 20 minutes from downtown Naples. ( no pets and no smoking)
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Find your slice of Paradise in this Newly Renovated, Spacious 1,400 Square Foot Condo.Located on the Top Floor, this End Unit boasts a generous size Living Room, Two Large Bedrooms (One King Bed and Two Twin Beds), Two Bathrooms, Dining Area, Kitchen and Large Corner Lanai which can be accessed from...
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Available annually, seasonally, weekly and monthly.Annual and Monthly (outside of peak season) - $ 2000 per month including utilities.Seasonal prices Jan - April range from $4500 - 5500 per monthIt’s gorgeous! Furniture all brand new!Take a look at this fully furnished, fantastic...
Featured review
Rented this condo for 2 months, Jan and Feb 2024, and enjoyed very much our first time in Naples as snowbirds from NY. The view from the screened in lanai is over the heated pool to the 10th green of the...
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Distance to beach: 5 miles to Delnor-Wiggins Pass State Park
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AVAILABLE FOR SEASONAL AND LONG-TERM RENT:May-Nov 2025 N/A Dec 2025 $7,000 Jan-Mar 2026 N/A April 2026 $$6,000 ask about other months11% Florida Tourist Tax is extra for rentals less than 6 months. 2 months term or longer is preferred. ASK FOR SPECIAL RATES FOR LONGER TERM RENTALS.3...
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Our property is a newly renovated 2-bedroom, and 2-bathroom unit located on the first floor of Cypress Woods Golf & Country Club. Cypress Woods is a hidden gem in North Naples offering a Golf course with narrow fairways and challenging greens, plus a dining room and banquet facility. There are two...
Featured review
We so enjoyed our February stay at your condo. It is so beautiful, and all appeared to be brand new. Soo clean and well decorated. It was so well stocked for anything we could have possibly needed and so...
Distance to beach: 6 miles to Bluebill Beach
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Newly renovated, fully furnished townhome in the heart of north Naples! 5 minutes from the popular Seed to Table grocery store/restaurant and other great restaurants close by. Less than 15 minutes from luxury shopping at Waterside Shops and other shopping centers. 10 minutes away from beautiful beaches. This...
Featured review
This townhouse is awesome. Super clean. Well stocked kitchen as well as beach equipment. The owner is awesome to work with and very responsive. If you are looking for a great vacation stay or seasonal...
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Stunning seasonal condo for rent beginning December 1, 2025 to April 30, 2026. 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...
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**JANUARY LAST MINUTE SPECIAL - $4,000 FEBRUARY - $5,000 MARCH - $5,500 APRIL - $4,200 (Please see cleaning, condo association fees and taxes listed below)Stay at our newly renovated 2 bed/2 bath Pavilion Club condo. Located just down the road from beautiful Vanderbilt Beach. The master bedroom...
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Tastefully decorated coastal condo in Naples, Florida. This 2 bed/2 full bath FIRST FLOOR (NO STEPS!!) unit features a large size master bedroom with a King bed. The guest bedroom features an on-suite pocket door so your guests may have full privacy. Our unit also has a screened in lanai which has a...
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 condo enjoys tranquil western facing sunset views and quiet nature where you can watch golfers putt on the green at the Quail Run Golf Course....
Featured review
Newly remodeled, completely outfitted condo. Owner is very accommodating and responsive to any requests. Location is superb to beaches, stores, restaurants. Totally positive experience for two years.
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Watch the sunrise over Moorings Bay in this perfect bayfront 2nd floor condo. It's all about the view and easy beach access just across the street. This residence includes your own private boat slip with room for a 30' boat, just minutes from Doctors Pass & direct, no bridge access to the...
Distance to beach: 12 miles to Tiger Tail Marco
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Home is located in desirable +55 development. Newer home, fully furnished with 2 queen-bed rooms, laundry room, and full kitchen. Screened in private lanai to RELAX while listening to the swish of coconut tree fronds sooth you into an afternoon nap. TV in very room. Gazebo on the canal to enjoy morning...
Distance to beach: 5 miles to Bonita Beach, Barefoot Beach
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Large Carriage House Condo FOR RENT @ , Florida. Available from April 2024.....minimum 30 day/monthly rental 3 bedroom + den + 2 baths, 1829 Sqft 2nd floor, lake view April 2024 - #4500+ Taxes & Fees May 2024 -Sept 2024: $3500/mo + Taxes & Fees October 2024 - Dec 2024: 4500/mo + Taxes &...
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Available: November, December 2024 & Season 2025 and off-season! Experience the perfect getaway in this beautiful two-bedroom condo, where stunning sunsets await from your screened-in balcony. The bedrooms boast new flooring, adding an elegant touch to your stay. Every detail has been thoughtfully...
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FEBRUARY OFFER: BOOK 6 NIGHTS-GET ONE FREE NIGHT. No expense was spared in the renovation, featuring elegant Travertine stone and marble flooring, captivating tray ceilings, and a welcoming country-contemporary indoor dining room. Each bedroom offers restful sleep on memory foam & pillow top mattresses,...
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...
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Gulf views with a public beach access right across the street!!* 90 day minimum*Location, location, location! Gulf views from the kitchen, living room, lanai, and bedroom!!! Harborside West has a gym, pool, and an updated community room with entertainment area. Relax poolside or take a stroll...
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Sunsets, Privacy, and Location...your own tropical base in Paradise. In the middle of Naples beaches, boating, restaurants, the newest shopping, yet removed in a gated tropical enclave. Open floor plan 3 bd. 3 ba. + den and lake lot on a cul-de-sac. Located in North Naples just steps or a short bike ride...
Distance to beach: 5 miles to Naples
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Immaculate beautiful upscale Tommy Bahama décor three bedroom, two bath very private end unit condo. This 2004 fully equipped condo boasts a beautiful tray ceiling and has been totally remodeled including:• Entire condo re-painted with custom paint colors • Newly remodeled kitchen...
Distance to beach: 0.9 miles to Park Shore Beach and Park
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Completely renovated, ground floor Belair Club condo in the lovely Park Shore neighborhood of Naples. Two bedroom, 2 bathroom with open living/dining/kitchen. All new appliances including a built-in refrigerator, induction cooktop, oven, microwave, dishwasher, kitchen aid mixer and in unit washer and...
Featured review
This pristine condominium is in an ideal location. There are so many shops and restaurants within walking distance and the beach is a short drive away. We enjoyed the friendly neighborhood and Tracy (the...
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This home blends coastal living with resort-style amenities. It has polished travertine flooring and an open, sun-filled layout. The home features its own heated pool, hot tub, and outdoor grilling area. Located in the gated community of Artesia, residents enjoy access to an impressive array of amenities...
Distance to beach: 5 miles to Delnor-Wiggins Pass
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NEW TO SEASONAL RENTAL MARKET! Discover Resort-Style Living in Sterling Oaks – North Naples’ Premier Pickleball & Tennis CommunityWelcome to Wildcat Cove in Sterling Oaks, one of North Naples’ most desirable gated communities, where this charming two-story home offers the...
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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,...
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Your Home Away From HomeEscape the everyday and immerse yourself in luxury with our exquisite resort rental townhome! Whether you're planning a family vacation, a romantic retreat, or a fun-filled friends' getaway, our spacious and beautifully appointed townhome offers everything you need...
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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Beautifully furnished 2-bedroom, 2-bathroom unit with a great view of the Royal Palm Golf Club. The private balcony offers a great view of the pool and whirlpool. In addition to a full kitchen, washer and dryer, three TVs, this second floor unit comes with a car port and storage facility.Come and...
Featured review
Golf , beaches and shopping all nearby. Medical and hospital equally accessible. Marco Island and Goodland 20 min south as well as Isle of Capri.
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Experience life and leisure at its best, directly on the Gulf of Mexico. Our private condominium is located in the Savoy on the exclusive 'North Gulf Shore Boulevard.' in Naples, Florida. The unit is a bright and spacious, two bedroom, two and 1/2 bath unit with spectacular views of the Gulf...
Distance to beach: 3 miles to Naples beaches
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This is a very nice two bedroom condo in Foxfire. It is on the top floor of a three floor building which has an elevator.It feels much more spacious and open than condos of similar size because the living room, dining room and kitchen have cathedral ceilings. You can't see the cathedral ceiling...
Distance to beach: 3 miles to Beach
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You will not want to leave! 10 minutes to famous 5th Ave and beautiful white sandy beaches! Huge heated pool! This is a very well equipped and spacious 2nd floor condo with cathedral ceiling in the living room/dining room area. The condo is tiled throughout and features fully equipped kitchen, 2 bedrooms,...
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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: 2 miles to Clam Pass
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Our MiraVista condo located directly on the Quail Run Golf Course. It is a beautiful 2 bedroom, 2 bathroom condo. The condo has a relaxing ambiance with stainless steel appliances in the kitchen. The unit has screen in lanai with amazing golf course views. Enjoy a cup of coffee in the morning while watching...
Featured review
The apartment is a dream. Everything was perfect. Very clean. Nothing is missing. The location excellent. Tatiana was extremely friendly from the first contact. She was always available and kept asking...
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Newly renovated, 3 bedroom, 2 bathroom condo! This condo overlooks a community pool and is located in beautiful Pelican Bay. This property provides beach access and only minutes from shopping and restaurants! 1 King, 1 Queen and 2 twin beds. 30 day minimum stay required.We are currently booked...
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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...
Distance to beach: 6 miles to Naples
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Steps away from the beautiful pool and clubhouse, this first floor, 2 bed, 2 bath condo is fully stocked, fully furnished and well appointed. Enjoy entertaining family and friends on warm nights on the screened-in lanai under the ceiling fan or in the cool central air of the spacious living room. New...
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A Boutique-Style Condo in the Heart of Old Naples, Florida. This vacation rental is located in a truly superb location, just a short stroll from all the excitement of downtown Naples. You’ll be delighted with immaculately furnished accommodations and convenient access to the pristine white sands...
Distance to beach: 3 miles to Naples Beach
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This boutique-style luxury rental is located in the heart of downtown Naples and was thoughtfully restored in 2023 with high-end finishes and furnishings. Embrace the modern coastal aesthetic, making it perfect for a long-term stay in beautiful Naples. You can easily walk or bike to the beaches, 5th Avenue,...
Distance to beach: 1 miles to Vanderbilt
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We still have other homes available Dec through Apr 2026 starting at $4,200 per month. Call 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 all included). Naples FL vacation rental.LARGE...
Featured review
Great property. Shane was excellent. We would stay again. We love Naples. Pool and hot tub worked great
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...
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This lovely condo has everything you need for a wonderful stay in Naples. Open plan large living area, with views over a natural preserve lake. The accommodation comprises spacious air-conditioned rooms with vaulted ceilings all decorated Florida style. Sterling Oaks has a fantastic Club House and...
Distance to beach: 10 miles to Naples Beaches
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A centrally located property. A quick drive to beautiful Naples beaches, close to famous 5th Avenue and so many restaurants and shops. The condo has new appliances, fresh paint and newer floors. The community offers a swim pool, hot tub, tennis/pickleball courts and bocce ball. The clubhouse is under...
Distance to beach: 2 miles to Vanderbilt Beach
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Our home is a beautiful spacious condo, completely renovated and everything in it is brand new - from the dishes to every piece of furniture. The kitchen is fully equipped. The condo is modern and comfortable. We enjoy many an hour sitting out on our lanai, which is a screened in porch, and never tire...
Featured review
Amazing first floor corner unit. Beautiful view. Very bright. Specious 2 bedroom with den. Huge master bathroom and shower. Enjoyed walks and bike rides in gated community. Enjoyed club membership. Great...
Distance to beach: 15 miles to Naples
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Great area - very quite. Located across from Lely Resort Golf course. 2 parking spaces (one covered). Lots of guest parking. Walk out your back door directly to the pool and spa area. The kitchen has been remolded with all new appliances. New floors and beds in both bedrooms. Includes all furniture and...
Distance to beach: 4 miles to Naples Beach
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Feels like a botanical village on the water! This unit is bright and open, multi-level 3bed/2bath (1 king bed & 2 full size beds in unit), with large volume ceilings. You can enjoy informal dining in the eat-in kitchen with breakfast bar, stainless steel appliances and granite counter tops. Includes...
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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....
Distance to beach: 15 miles to Marco Island
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2 bedroom 2 bath first floor end unit. Fully furnished including linens. Newer appliances and washer and dryer. Fully furnished kitchen, screened lanai, cable TV, Wifi. Heated pool, hot tub, tennis and pickle ball courts, bocci courts and assigned parking place. Near Marco Island and Naples beaches....
Featured review
Very nice condo in a wonderful location, nice friendly owner, great pool with a hot tub, condo has everything you could possibly need and was very clean, we will rent again!
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Amazing 3BR/2BA Amenity Rich Naples Paradise Vacation or Short Term/Longer Term TURNKEY Fully Furnished and appointed Condominium - This very popular luxury appointed luxurious and spacious amenity rich San Pablo floor plan is being leased turnkey/furnished and has three bedrooms, two full baths, two-car...
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This condo can be used as either a one or two bedroom apartment and is part of a beautiful property setting (Park Shore Resort) with individual units surrounding a tropical island holding a large swimming pool, a sun deck, large barbecue area, outdoor whirlpool, a restaurant/bar at poolside, and beautiful...
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This spacious, very beautiful, light and romantic Villa is located West of 41 on Vanderbilt Drive in the gated community of The Villages of Emerald Bay. The ground floor home features a split bedroom floor plan, a private lanai and an attached garage with additional parking. Newly decorated, the...
Featured review
In the Wizard of Oz, Dorothy clicks her heels three times and says, “There’s no place like home.” Those words reflect the feelings of most of us about where we live. Home is more than a place. Home...
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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