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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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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.
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...
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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...
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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...
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Distance to beach: 6 miles to Vanderbilt Beach
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Fully furnished with all necessary amenities, 2nd floor, 2 bedrooms - main bedroom has a queen bed, 2nd bedroom has 2 twin bed, 2 full baths, 1 car garage plus additional parking spot. Lanai with a great fountain view, perfect for your morning coffee or just to relax and read a book. Gated community...
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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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Prepare to be inspired by this impeccably designed, professionally decorated, and meticulously landscaped ranch-style residence, ideally positioned along the 14th fairway in the prestigious Esplanade Golf & Country Club of Naples. Overlooking serene lake views, this home offers the perfect blend of...
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A beautiful twin Villa 3 Bedroom 2 Bath 2 Car Garage attached at Reflection Lakes of Naples. This Villa is tastefully done with a relaxing view of the lake from back patio. Amenities include lanai overlooking the lake, heated swimming pool, community center, fitness center, billiards, game room, and...
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: 6 miles to Lowdermilk Park
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This gorgeous villa will make your Florida vacation unforgettable. The villa is located in a gated community with a magnificent view of a lake.Enjoy 2.500 ft² of air-conditioned living space with 3 bedrooms and 3 bathrooms and a den with pullout sleeper for 2 persons. You can use the den as an...
Featured review
We had an absolutely fantastic stay at this vacation house within a gated community! From the moment we arrived, everything exceeded our expectations. The property was spotless, beautifully decorated, and...
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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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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...
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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...
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Three bedroom, two bath fully furnished corner unit on the top floor with some very nice updates. Open floor plan, vaulted ceilings and screened balcony in a serene and peaceful setting yet, located in the heart of Naples. Newer appliances with all hard surface floors throughout, painted neutral colors,...
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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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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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...
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This newly in 2017 built dream house with 4 bedrooms and 3 bathrooms is located in a quiet location in a cul-de-sac overlooking the Hibiscus golf course. Due to its central location, you can reach numerous restaurants and shops in just a few minutes. The spacious house has an air-conditioned living...
Featured review
We had a great time in Naples in January. The house was nice and clean and there was plenty of walking and bike riding in the area. We will stay there again!
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,...
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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...
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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11 story condo directly on beautiful Vanderbilt Beach. Completely remodeled lobby with common area with kitchen for parties. On site mgr. Total pool remodel, completion estimate September 2025. Beautiful sunset views from the 270 sq foot veranda on eight floor. Free Wi-Fi, fully equipped kitchen,...
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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...
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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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Nicely decorated fully furnished, second floor condo (w/elevator)with gorgeous water and natural preserve view. Private designated covered parking spot also included. This condo is located in the private and gated Treviso Bay Golf & Country Club in Naples, Florida. It is a spectacular TPC (Tournament...
Featured review
Outstanding golf and country club with 1400 homes ranging from low rise condo buildings to streets of beautiful detached houses. Miles of manicured roads and sidewalks, a treat for walkers, joggers, cyclists...
Distance to beach: 11 miles to Delnor-Wiggins Pass State Park
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Heritage Bay Condominium-- Have yourself a five star vacation! Well cared-for, 1st floor, two bedroom 2 bath condo.This young, freshly painted ( 2024 ), two bedroom unit has a fully-equipped kitchen with stainless steel appliances, Corian countertop, raised panel cabinetry, and a convenient separate...
Featured review
Spent 4 months at this condo in Naples. The unit is located at heritage bay. The condo is beautifully furnished along with all the amenities included. We had such a wonderful time. We were near all of the...
Distance to beach: 5 miles to Lowdermilk Park
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The modern furnished villa with 2.000 ft² has 3 bedrooms and 2 bathrooms. Each bedroom has a flat-screen TV. In the spacious living and dining area you can find a place to relax on the couch. The large LED TV in the living room is connected to the Internet and also has a German program.Meals...
Featured review
The villa is eccellent clean, a lot place and the equipment ist nearly perfect. Everything is there, you will miss nothing!!!
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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...
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...
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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,...
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Welcome to our newly decorated and fully furnished home! Available now for 2025. Feel the warmth of the beach the moment you step into this beautifully decorated 3 bedroom plus den, 2 bath coastal decorated home. Newly painted with Peruvian travertine 18x18 tiles throughout house except for bedrooms....
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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Take a break and unwind at this peaceful oasis. Less than five minutes walk from the beautiful Vanderbilt beach, bring your favorite beach attires and relax for a month? Why not more? It is beach time EVERYTIME! This condo has been newly renovated!
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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...
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Our private peaceful renovated Villa with 17 foot ceilings and a relaxing water view at the back of the Villa await you. Regent Park Villas are a community of Villas and private homes in a very friendly, house proud community that is extremely well maintained by the association and the private home ownersThe...
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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...
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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Available for the 2025 Off-Season starting May through November with TPC Golf transfer! PET FRIENDLY! Turnkey furnished Napoli Coach Home, 1883 sq. ft. beauty with a 2-car garage and a gorgeous lake view. First-floor end unit with 3 bedrooms, 2 baths, golf included for tenants on the TPC Championship...
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FOUNTAINS I in Naples.Fully FURNISHED TURNKEY FIRST FLOOR condo with carport AVAILABLE mid-April until the end of November 2025 for only $1950 a month (December 2025 is $3500). (Not available for season 2026). Beautifully REMODELED and furnished 2 bedrooms, 2 baths with gorgeous LAKE VIEW. All new...
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Located in Bermuda Bay II at Bay forest close to Barefoot and Wiggins Pass Beaches. Bright condo with a private garden view. Pickle ball, tennis , shuffleboard and miles of walking and biking paths including a boardwalk through a nature preserve ending at a Tiki Hut to enjoy spectacular sunsets. Numerous...
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...
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This family owned and managed second floor property is located in the quiet Naples Keep community within the highly sought Palm River Estates. Amazing location. It's a very livable, quiet, clean, and comfortable condo with new living room furniture, television, and split king bed (with power adjustable...
Featured review
We rented this condo in feb & March 2022. It was very nice w/ everything we needed. Loved the pool & met very nice people in complex area. Susan & Bruce were so accommodating. Always available & so honest...
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This recently renovated condo is just steps away from the pool which sits on the serene lake and is surrounded by lush tropical trees. Our condo is situated within a gated community with 24 hour security. The first floor condo (no stairs to climb) features two bedrooms separated for privacy by the...
Distance to beach: 4 miles to Vanderbilt Beach
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***KEY FEATURES*** 3 Bedroom - 1 King, 1 Queen, 1 full w/ 2 twin mattresses 2 Bathrooms - with shampoo, conditioner and body wash Large Connect 4 game Outdoor Dining area located in lanai Smart TVs Washer/Dryer on premises Private Heated pool with safety fence provided Private Hot tub***CUSTOMER...
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: 2 miles to Delnor-Wiggins State Park Beach
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One of the best locations in Naples, located at Imperial Golf Resort, Park Place community. Cul-de-Sac Street, just a short walk to the pool with heated water, nature trail across the street, 5min drive to the closest beach & Mercato, about 12min to 5th Ave. full of shopping and fine restaurants...
Featured review
My wife and I stayed at this property from January through April 2025. Beautiful area, a short drive or bike ride to Delnor Wiggins or Vanderbilt Beaches. A 30 second walk to the community pool overlooking...
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Lanai: Lazy on the couch or enjoy a bite at the table...the view is always outstanding. On a cool night, curl up under the cozy comforter and read.Master Bedroom: tuck into the King 4 poster bed and watch TV, use the stable internet to get some work done at the desk, enjoy a shower in the recently...
Featured review
Our family’s first visit to Naples was amazing - the rental was beautifully decorated, very clean and had everything we needed. The master bedroom was gorgeous and the kids room was perfect. My favourite...
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 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!
Distance to beach: 6 miles to Vanderbilt Beach
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Modern open concept 3 Bed, 2 baths, one car garage first floor unit located in the Vineyards community, this property features updated kitchen with island, quartz countertops and new appliances. New luxury vinyl flooring throughout the home ). , nest thermostat.The Lalique pool and clubhouse are a few...
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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