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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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The Captain's Cottage is a everything you hope for when staying in Naples! The home is a spacious five bedroom villa with a large pool overlooking a waterfront view. This property has been designed with an elegant coastal vibe with plenty of areas to entertain and relax. Located in Naples' famous...
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: 100 yards to Vanderbilt Beach
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A beautifully renovated condo nestled along the bay, exuding coastal elegance. The inviting interiors feature comfortable furnishings, stylish accents, and vibrant hues, creating a tropical oasis. This end unit offers breathtaking views of the Gulf of Mexico to the west and the serene bay to the east....
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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: 4 miles to Vanderbilt Beach
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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
This condo was the perfect place to unwind and enjoy everything the Naples area has to offer. The space feels calm, fresh, and very intentionally put together—nothing cluttered, nothing overlooked. It...
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This home is truly what living in Olde Naples is all about! A spacious home great for entertaining, enjoy the outdoors on the verandah or out by the pool, walk to the beach, and easily enjoy Fifth Ave and Third street shopping, dining and entertainment! Open & bright, loaded w/upgrades! Absolutely...
Distance to beach: 50 yards to Across the street
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Enjoy your vacation in Huntington Lakes, a vibrant community in North Naples. This light and airy first-floor condo offers 2 bedrooms, 2 bathrooms, a detached carport, and 1 assigned parking space. The master bedroom features a queen-sized bed, a peaceful lake view and an ensuite bathroom. The secondary...
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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The Three Palms is a unique courtyard style pool home with all of the amenities you would expect from new construction. Courtyard style pool home features 4 bedrooms and 3 baths. Reclaimed heart pine floors throughout. Gourmet kitchen features oversized Island, 48" Sub zero fridge and Wolf 6 burner...
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Welcome to the "Kite House" a one of a kind Old Naples family compound only steps toThe Gulf of Mexico. This fabulous new Naples Beach Retreat is comprised of three residences sleeping up to 16 people. There are 3 residences comprised of a 3 bedroom, 2 bedroom and one bedroom cottage. The 2...
Distance to beach: 1 miles to Vanderbilt Beach
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Southern Exposure, 3 br plus a dedicated office space and pet friendly. A spacious and inviting floor plan with vaulted ceilings, large kitchen, laundry inside the home. . . Walk or bike to Vanderbilt Beach and Delnor Wiggins State Park and Beach. . . Very nicely furnished with a coastal cottage decor...
Featured review
We really enjoyed our stay. The house was very clean and had everything we needed. We loved sitting in the shallow area of the pool or having a drink while watching tv under the covered porch. Thank...
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The home is located on Duck Chanell, Aqualane Shores, Naples. At the bottom of the street is the Gulf of Mexico incredible beaches.Three bedroom (King, Queen, two double beds). Three full bathrooms. The living room has a fold out sofa bed.The home is extensively renovated. A beautiful pool...
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This home is truly what living in Olde Naples is all about! A spacious home great for entertaining, enjoy the outdoors on the verandah or out by the pool, walk to the beach, and easily enjoy Fifth Ave and Third street shopping, dining and entertainment! Wonderful & well-built in 2007! Open & bright,...
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Available between Aug 4, 2026 and Oct. 25 2026. Kick back and relax in this calm, stylish 1BR penthouse with saltwater pool, gym, and clubhouse access. What I love about this space is that it is perfect for 2 people and is flooded with natural light. Being on the top floor means no overhead neighbors,...
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Spacious 1st floor condo-amazing golf views, fully furnished. New hardwood floors, new Master bedroom with King bed, New Queen bed in 2nd BR with New dream-like mattresses. Murphy console-LR makes to Queen for extra sleeping. Both bathrooms/closets completely redone very stylishly. Desk for working...
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THIS UNIT IS AVAILABLE FOR JAN/FEB/MARCH/APRIL of 2025This beautiful 3 bedroom 2 bath condo is professionally decorated and immaculately kept to perfection. The bedrooms are equipped with a King bed in the master bedroom, and Queen beds in the guest bedrooms. The Great Room features a 60" Television,...
Featured review
Wonderful condo. Comfortable, clean, great location. Love everything about this place and the Dunes
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Perfect winter getaway! Lovely 2BR/2BA condo overlooking lake surrounded by lush tropical landscaping. Well maintained and has everything that you will need to enjoy your stay in paradise. Key Royal is a well-maintained community in excellent location with plenty of shopping, new dining options and the...
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: 3 miles to VANDERBUILT BEACH
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This meticulously maintained first-floor condo is situated on the 16th hole of a pristine golf course, offering picturesque views of both the serene lake and lush fairways. The property features two well-appointed bedrooms, two bathrooms, and a spacious den, providing ample living space. A large lanai...
Distance to beach: 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...
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Welcome to your own slice of paradise in Naples, Florida. Nestled in a prime location, just 5 blocks away from the vibrant 5th Avenue shops and restaurants, and a mere 2 blocks from the sun-kissed beach, this opulent 3-story estate is a dream come true. With 6 spacious bedrooms, this residence exudes...
Distance to beach: 9 miles to Vanderbilt Beach
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A fully furnished Veranda I Condominium in beautiful Heritage Bay (HB) is available for annual rental, or seasonal rental, effective through all of 2025-7. This is a 2-bedroom unit with a Den/Office that also has a pull-out sofa bed. Rental also includes a 1 car unattached garage. Full golf membership...
Featured review
Our stay at this rental was awesome! We lacked for nothing in this fabulous space. Jim has thought of everything!
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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: 6 miles to Naples City Beach
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Situated on one of the largest lots in Glen Eagle, the house has over 2,300 square feet living space, enough for the entire family! The house has 3 bedrooms and 3 full bathrooms, spacious living room, separate dining room. The kitchen has granite counter tops with large island and breakfast bar. The large...
Distance to beach: 0.2 miles to Vanderbilt Beach
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You’ve just found your perfect Vanderbilt Beach vacation condo! Beachwalk of Vanderbilt Beach is just one and 1/2 block from the beach entrance and shopping. Gated community with a beautiful community pool, tennis courts and fitness center for your enjoyment.Walk to the beach to watch gorgeous...
Featured review
This excellent property was exactly as described. It is set in a lovely, quiet location and within walking distance to the beach. It was extremely clean, spacious and comfortable. It was beautifully furnished...
Distance to beach: 1 miles to VANDERBILT BEACH/WIGGENS PASS BEACH 2
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Love the beach? Located in north Naples just steps or a short bike ride to sugar sand Vanderbilt Beach and Delnor Wiggens State Park. Watch the dolphins as you enjoy a walk on over six miles of beautiful beaches. Relax in our private pool and spa in the enclosed lanai with a view of the lake or check...
Featured review
We stayed at Renee & Dan's home for 5 weeks from early January to early February. We are from Missouri and the weather can get a little cold. On an earlier trip to the Naples area, we fell in love with...
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This beautiful condo is located in the extremely desirable active Huntington Lakes, which is just minutes from all of the amazing shops, restaurants and the BEACH! This 2-bedroom condo, is fully FURNISHED and stocked with everything that is needed. It is a gated community with plenty of activities such...
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Dream Villa in Naples ReserveExperience luxury living in this stunning 3-bedroom villa located in the exclusive gated community of Naples Reserve, South Naples. Just minutes away from the famous 5th Avenue, world-class golf courses, pristine beaches, fine dining, shopping, and beautiful Marco Island.Highlights...
Distance to beach: 1 miles to Vanderbilt Beach
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BRAND NEW ON THE RENTAL MARKET WITH AN OPEN CALENDAR FOR YOU TO CHOOSE YOUR PREFERED DATES!! Beautiful 3 bedroom home with southern exposure located in the desirable 600 block. Walk, cruiser bike or take our local shuttle service to Vanderbilt Beach! This home offers an open floor plan, high ceilings,...
Featured review
We loved this home! The location in north Naples was ideal- close to Mercato, Vanderbilt Beach / Wiggins state park. The home is EXCEPTIONALLY well equipped in every way from PLENTY of beach towels, to...
Distance to beach: 4 miles to Vanderbilt Beach
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This comfortable and well-appointed home is designed for easy, longer stays—whether you're here for a week, a month, or just need a peaceful break.With plenty of space to spread out, a fully equipped kitchen, and inviting indoor/outdoor living areas, it’s ideal for couples, families,...
Featured review
This house was clean and located perfectly near all the beaches , shopping and restaurants! The back yard was paradise with a pool , jacuzzi and lanai with TV ! We can’t wait to go back !
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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...
Distance to beach: 10 miles to Tigertail Beach, Marco Island
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FULL GOLF MEMBERSHIP IS NOW AVAILABLEApr-May 2026 $8k/mo Jun-Oct 2026 $5k/mo Nov 2026 - Apr 2027 N/A May 2027 $8k/mo ask about other monthsThe social member benefits are included in rental fee, full golf rental membership is available for an additional fee per Eagle Creek Golf and Country...
Distance to beach: 4 miles to Naples Beach
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This Naples condo is just what you are looking for. It boasts nearly 1300 sq. feet of living with a coastal chic style. There are two large bedrooms and two full baths. This top floor unit (2nd story) condo has high ceilings and plenty of brand new windows to let in the beautiful Florida sunlight. A 6...
Featured review
We loved our stay! The condo is very spacious and very clean. Everything is provided for you to enjoy all types of activities. The pool was fabulous and everyone was so friendly.
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Welcome to The Cambier Cottage, a charming vacation home nestled in the heart of Olde Naples, Florida. This delightful retreat seamlessly combines comfort, convenience, and artistic flair. Expertly handcrafted by a talented local Naples artist, every corner of this three-bedroom, three-bathroom haven...
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1st Floor and nestled into the serene nature preserve, the Palms has been completely remodeled. The Heated Pool (always set to 89 with a Waterfall) is also just 30 steps away. This is also the best location in all of Lely! Kick back and relax in this calm, beautifully redesigned space. Relax on the Lanai...
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...
Distance to beach: 8 miles to Naples Beach
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Currently accepting Requests . Rates as follows: Current Date May-December 2025 Rate 2,500+++ .January 2026 $5,500 +++ February 2026 $5,500 +++ March 2026 $4,400+++ April 2026 $4,000+++plus +++ represents three...
Featured review
Great location of condo outstanding communication with owner can’t wait to come back ; great golf course very friendly staff
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Fully Furnished, Spacious Accommodations: Awesome Apartment near the Beach in Naples offers a spacious apartment with two bedrooms and two bathrooms. The property features a fully equipped kitchen, air-conditioning, and a private pool.Exceptional Facilities: Guests can enjoy a spa and wellness center,...
Distance to beach: 3 miles to Delnor Wiggins
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British owned second floor modern condo newly decorated. 2 bedrooms (king size bed in master and 2 singles in second bedroom) 2 bath condo + den and pull out double sofa bed. 3 TVs and WiFi. Ideal for golfers. Overlooks 17th green and lake. Elevator available. Lanai with outside furniture. Pool...
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AVAILABLE from April 1st 2026 !!! Minimum 1 month rent. Great location !!! Clean and neat first floor 2 bedrooms, plus den, 2 full baths unit in Coach Home. No stairs. Beautifully remodeled. Plank tile, freshly painted, new stainless steel appliances, new kitchen quartz countertop, recess lights,...
Distance to beach: 1 miles to 1st Avenue Beach
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Gorgeously furnished oversized fifth floor two bedroom with balcony and sunset views. 1111 Central development offers large zero entry pool with two spas, thoroughly equipped gym, game room, theatre room, co-working space, BBQ facilities and much more!15 minute walk to beach, 10 minute walk to 5th...
Distance to beach: 4 miles to Bonita Beach
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Beautiful Coach home in the Gated neighborhood of Sterling Oaks. Sterling oaks offers resort style pool with a tiki bar that has wonderful food and drinks. The club house offers dinner every Friday night and pub night on Tuesdays nights. You can also join the many events and leagues we offer during...
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: 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 freshly renovated condo enjoys tranquil western facing sunset views and quiet nature where you can watch golfers putt on the green and tee...
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Featured in Naples coffee table books "Dream Homes" FLAMINGO PALMS is one of Olde Naples finest homes superbly located in the heart of Olde Naples historic district. Walk to some of Naples finest restaurants and shopping along Olde Naples Famous Fifth Avenue, Just 2 blocks away. Enjoy a round...
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Why settle for ordinary when you can have EXTRAORDINARY-the BEST of the BEST for your Naples getaway! Experience the epitome of coastal luxury in this three-story GULF-access estate home with a private dock and boat lift, perfectly positioned on the widest canal in the prestigious Conners neighborhood...
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This home is located only three blocks from the beach! Enjoy a beautiful back yard living space, completely enclosed by greenery for privacy and beauty while you enjoy the pool, hot tub, or fire pit along with full outdoor grilling area. Renovated interior with an open kitchen / living room, this home...
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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...
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Enjoy our 3-bedroom + office, 2-bathroom home in the Glen Eagle Golf and Country Club community of Naples. Enjoy stunning views of the 10th green and 11th tee box right from your private pool and hot tub. Home has been completely renovated from top to bottom. Monthly rentals only - golf membership is...
Distance to beach: 10 miles to Naples and Marco Island
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Our second floor condo in Coral falls, Lely, Naples has a bright and spacious feel, beautiful views and has all your needs for your home away from home while. The building is equipped with an elevator, as well as two separate stair cases. The primary suite sleeps two in its King size bed. The EnSuite...
Featured review
! had the most relaxing stay at this Florida condo! The location couldn’t be better—just a quick drive to beaches, shopping and dining.The condo was spotless, stylish, and incredibly cozy. I loved...
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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