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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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Beautiful lakefront end unit on the first floor. The master bedroom has a king sized bed. Second bedroom has two twin beds. Entire condo has been painted in December 2020. Kitchen renovation completed in January 2021. The amenities include wifi, cable tv, washer and dryer. Community has a large...
Featured review
We stayed at Marco’s condo for six weeks and had a fantastic time. Upon arrival we found the condo in spotless condition. Normally when we rent we always need to do some cleaning but not in this case....
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A Quaint 2/2 with a private carport is on a golf course with 6 different pools clubhouse and many more amenities. Open Family room to kitchen and with a lanai. Shopping, Downtown, great restaurants and the beach all very close by.
Distance to beach: 6 miles to Many
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Very social building ! Brand new clubhouse opened Spring 2025 featuring 3 dining venues, 2 outdoor bars, and a beach entry pool with food and beverage service available. This 15 million dollar renovation makes Countryside the place you want to spend your winter. Super clean and comfortable 2 bedroom/2...
Distance to beach: 10 miles to Marco Beach, Tiger Beach, Naples Beach
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" If you are looking for a beautifully furnished beach house, you have arrived! No expense has been spared, and no detail has been overlooked in this two bedroom two bath condo. Enjoy the beach house ambiance with a separate outdoor kitchen overlooking a spectacular lake view on the 300 square foot...
Featured review
In 2024, we stayed in this lovely condo from February 7 to May 6. We had planned to be there February 1 through April 30, but we were unable to leave as planned; the owners graciously extended our departure...
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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...
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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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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 Delano Wiggins Park
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We also have TWO virtually identical units that are EXTREMELY PET FRIENDLY at a neighboring gated community with loads of amenities where we can allow up to TWO PETS ANY SIZE! Please call us at two, three, nine, five, nine, five, nine, one, six, zero.Welcome to your Happy Place that checks all...
Featured review
We rented this property from May till October. It has a great location and close to everything!! Grocery stores, Walmart, Sam’s Club. Great places to grab breakfast, lunch and dinner. Downtown Naples...
Distance to beach: 6 miles to 5th ave
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This is a ground floor condo, 2 bedroom, 2 bath fully furnished with over sized garage located in Falling Waters which is centrally located between Marco Island and downtown Naples.Falling Waters Beach Resort has two pools, two tennis courts and one boccie court. One pool is a heated 600 foot lazy...
Featured review
Hallo We are 2 persons and want a Apartment with 1 or 2 bedrooms about Naples fore middle Januar for 4 /6 weeks. What can you offer fore us? Best regards Birte and Eckhard Schmidt Bremen Germany
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Our Property is owned and has been very well maintained by us! 1st Floor Unit which has an incredible view of the Lake from the Lanai.2 Bedrooms, and 2 Full Baths as well as a separate garage for parking your vehicle, and also a separate parking space!The condo is equipped with all semi new appliances,...
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Beautiful fully renovated 2 bedroom 2 bath apartment in Heritage Bay community. Rental comes with full access to 27 hole golf course on property as well as all amenities in the complex such as the pool, tennis, bocce, bike trails among others!!We also have another similar condo in the community (2...
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Available March, and April! Welcome to your luxurious downtown retreat! This exquisite residence is nestled within the esteemed 780 Fifth luxury condominiums and showcases an expansive open floor plan, featuring a recently updated kitchen with modern cabinetry, quartz countertops, a chic bar area, two...
Distance to beach: 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...
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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)
Distance to beach: 7 miles to Lowdermilk Park
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2B/2B 1st floor fully furnished condo in a quiet community with 2 pools(1 heated). Tiki Huts by pool and bathroom cabana. Parking directly in front of unit along with mailboxes. 1 Q bedroom with cable, 1 Q bedroom with TV for streaming and sofa bed opens to full in LR. Great location with a short drive...
Featured review
This condo is in the perfect location- within driving distance to the beach, nightlife/restaurants, and downtown shopping center! We loved how quiet the neighborhood is and that the complex offers 2 pools...
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...
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...
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
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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 stunning view, then head out to explore — you’re just minutes from...
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...
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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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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...
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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...
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NORTH NAPLES - Second Floor 2/2, beautifully renovated, fully furnished condo for annual or seasonal rental. Located in desirable community of Emerald Lakes. This prime Naples location is just minutes from I-75, and close to beaches, shopping, and dining. This condo offers open floor plan with cathedral...
Featured review
Meine Frau und ich hatten von Anfang Oktober 2025 bis Anfang Novemer 2025 die Wohnung gemietet. Die Begrüßung mit einem Gastgeschenk durch Dorota war sehr schön. Dorota war immer herzlich,ansprechbar...
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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: 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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PROPERTY IS BOOKED NOW through November 1, 2025 & DECEMBER 31, 2025 - APRIL 15, 2026 - All other dates are availableRelax and enjoy some time on the lanai overlooking the pristine lake. Custom lighting throughout. On-site property management: indoor & outdoor basketball/pickle-ball courts,...
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...
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Beautifully furnished, two story townhome available for rent in-season or annually. The home has three bedrooms and a loft with a pullout sofa. It comes completely turnkey with everything you need to enjoy your 3-6 month stay in Naples. It is approximately 20 minutes to Vanderbilt beach. The community...
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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,...
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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This luxury community has a cosmopolitan atmosphere amid lush natural surroundings ,with a luxurious pool adjacent to the clubhouse . set in Naples Florida, The Reserve is just minutes from the beautiful beaches, and a short drive to highly desirable Fifth Avenue shopping districtEnjoy the Florida...
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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...
Distance to beach: 5 miles to Pier Beach
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Escape to serenity in our meticulously furnished 2-bedroom, 2-bathroom condo located in the exclusive Falling Waters community. This upscale retreat promises a dream getaway with a perfect blend of comfort, privacy, and convenience. Key Features: • Unmatched Tranquility: Nestled in Falling Waters,...
Featured review
We stayed at Falling Waters for 3 months last winter. It was exactly what we needed. We loved the resort style pool and the very large lanai. We appreciated the great communication (before and during our...
Distance to beach: 2 miles to Lowdermilk park
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6-bedroom vacation home just 3 minutes to Naples Beach with 3 king ensuites.In the heart of Naples' charming neighborhood lies this beautiful 6-bedroom vacation house. Imagine yourself relaxing by the heated private pool, soaking up the sun and enjoying the refreshing breeze. With free WiFi,...
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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This adorable first floor Castleton Gardens condo in Naples is the perfect home base for your trip! Gated community location...walk anywhere. This welcoming and newly renovated space has everything you need and is right across from the community pool, terrace, and hot tub.Recently remodeled with...
Featured review
You will feel right at home the moment you step in this lovely condo!! Tastefully designed and very well-appointed with all the amenities needed to make for a comfortable stay. Exceptionally clean and...
Distance to beach: 3 miles to Vanderbilt Beach
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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 few areas in Naples that allow tenants to have up to two pets of any size! We have two other nearly identical properties!...
Featured review
We stayed here for 3 weeks. The condo was as described. Everything we needed was there and the house was clean. The complex has a great club house, work out facility and large pool and hot tub. The...
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What a view! Beautiful second floor unit at Huntington Lakes, a gated community in North Naples. Just a few minutes away from top-rated restaurants, shopping and the beach.This fully furnished unit comes with everything you need for a comfortable and convenient stay. It has been completely updated...
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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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This beautifully decorated condo is perfect for your short term or long term stay. Soak up the sun at our cozy condo ! it is just a 5 minute bike ride from Clams Pass beach and Fine shopping and dining at Waterside Shops.Our condo is equipped with everything you need for a wonderful stay in Naples!...
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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...
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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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We are offering our elegant and spacious, fully furnished 2 bedroom, 2 bathroom Villa located on a lovely private Naples community of Walden Oaks. Entering the charming “Walden Oaks” community you will come across the large lake with an Island heated-pool, bordered by tall and lovely palm...
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AVAILABLE MARCH& APRIL 2025 !!! 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, fully equipped kitchen,...
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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Gorgeous 3 bed/2bath furnished condo only three miles form one of the finest beaches in Florida. This second floor end unit comes with lots of bright sunlight and everything has been updated. Enjoy a fantastic full view overlooking the all natural Florida preserve and clubhouse which is spectacular after...
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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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Welcome to your BEAUTIFULLY renovated home away from home! Be the first guests to appreciate the new quartz kitchen, brand-new furnishings and designer coastal decor. This light and bright home feels extra spacious thanks to soaring ceilings and an abundance of windows. Enjoy stunning water views, offering...
Featured review
We spent the month of October here and it was perfect for what we needed. It was close to all types of shopping and many restaurants. The renovation was well done and it was very well equipped and supplied...
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...
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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