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Welcome to The Pier House, an Old Naples masterpiece where timeless coastal style meets top-tier finishes. With just over 5,200 square feet and a resort-style courtyard pool, the home lives like a private sanctuary—perfect for long, lazy beach days and golden-hour strolls to the Naples Pier for...
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Listed rate is for High Season (Nov. through April). Longer High Season leases have greater discounted rates. Annual Rate is $40,500 per month. Located only two blocks to the beach and featuring lush, mature tropical foliage, this classic Bermuda styled home offers absolutely stunning interiors. The sprawling...
Distance to beach: 0.9 miles to Naples Pier
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Experience the best of Old Naples at Sun Dial 295 — a stunningly reimagined two-bedroom retreat in one of Naples’ most sought-after locations. This residence blends sophisticated design with coastal elegance, offering the perfect balance of luxury and convenience just steps from world-class...
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Experience the ultimate in Florida luxury at this stunning 3-bedroom + loft and 4-bathroom coastal contemporary condo, offering 2,524 sq. ft. of thoughtfully designed living space. This high-end unit has been fully remodeled to combine modern sophistication with timeless charm.Step inside to discover...
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Newly remodeled condo in a small complex. Ground floor. Master Bedroom has King size bed, plenty of closet space and private bathroom. Second bedroom has Queen size bed. Both bathrooms have walk in showers. Open floor plan for kitchen, dining and living room area. Kitchen is well equipped. Screened Lanai...
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Distance to beach: 0.2 miles to Old Pier Pilings
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White Sands is an updated old Florida style resort located in the heart of Old Naples and is an easy walk to the beach, shopping and dining on Fifth Avenue. White Sands Club offers a relaxed atmosphere with a heated pool and spa tub, outdoor BBQ grills and shuffleboard with bicycles, beach umbrellas,...
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The best part of this place is the location - 2 short blocks to the beach. It is clean and the grounds are very well maintained. Pool is nice and warm. A 1-bedroom is perfect for a small family with eat...
Distance to beach: 0.4 miles to Gulf of Mexico Naples Beach
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A large Villa with a private courtyard, pool and spa. Recently remodeled with a full kitchen, master suite and three additional bedrooms. A private garage with two extra parking spaces and guest parking.Centrally located, 3 blocks from Historic 3rd St South, 5 blocks from 5th Ave South, 4 blocks from...
Distance to beach: 800 yards to 4th ave south
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Discover a hidden gem in the heart of Naples, FL! This spot at just off 5th Avenue South is a cozy 1,000 square foot space that's just waiting for you to make it your own. It's the perfect home base if you're planning to explore all that Florida has to offer. Picture this: You start your...
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All about the prime location!!! You will not find a better deal than this immaculate downtown condo. Nestled in the center of Olde Naples only two blocks from 5th Avenue South and just a short walk or bike ride to the famous white sand beaches of SW Florida. This light and bright corner unit has been...
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We had a wonderful time here on our vacation. The property worked perfectly for our family. We will definitely stay here again when we visit!
Distance to beach: 50 yards to 5TH AVENUE BEACH
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TWO BEDROOMS EACH HAVE A KING BED ,MULTIPLE DRESSERS AND AMPLE CLOSET SPACE TWO FULL BATHROOMS EACH CONTAINING A SHOWER AND TUB COMBINATION GROUND LEVEL PRIVATE OUTDOOR PATIO WITH BEAUTIFUL ORCHID GARDEN OVERLOOKING 5TH AVENUE LARGE OPEN LIVING DINING AREA LARGE FULL KITCHEN WITH A LARGE NUMBER OF...
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Very nice, spacious condo, as advertised. Excellent position near to the beach and restaurants. Perfect for a couple. Randy and Amy were great hosts, very helpful, an easy check in. Would highly recommend....
Distance to beach: 1 miles to Naples Pier
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Welcome to your dream vacation rental in downtown Old Naples! This beautifully curated, upscale 2-bedroom condo offers an unmatched blend of luxury, convenience, and style.Perfectly situated to enjoy all the charming amenities of Old Naples, you'll be within walking distance to the shops on...
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Enjoy sunny Old Naples at reasonable rates, 75 yards to the beautiful beaches of Old Naples at a charming guest house efficiency on an estate property. This property is located in the heart of the most exclusive section of of Old Naples, steps to the Gulf of Mexico and the fine shops of Fifth Ave and...
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Welcome to the heart of beautiful, sunny Naples! Your new home away from home.This 2 bedroom, 1 bathroom apartment is centrally-located in the Downtown of Naples. Everything is within walking distance or minutes drive away. Shops, restaurants, bars, & the beach. You’ll love your time spent...
Distance to beach: 1 miles to little over a mile
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NEWLY RENOVATED 1 STORY END UNIT NEAR NAPLES BAY RESORT WITH A DOCK TO ENJOY THE WATERFRONT BOATS & BIRDLIFE. THERE ARE 2 BEDROOMS EACH HAS ITS OWN BATH. MASTER HAS NEW KING BED AND 2ND HAS NEW QUEEN BED. FLAT SCREEN TVs IN BOTH BEDR0OMS AND A 75" TV WITH FREE THE MAIN OPEN FLOOR PLAN AREA....
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Our stay at Elina and Sami's place has been delightful. They thoughtfully stocked the kitchen, tastefully decorated the condo, and provided exceptionally comfortable beds. Having a puzzle table was a wonderful...
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Perfectly located vacation home in the heart of Olde Naples offers a peaceful and private retreat. Available January - April 2026. This highly desirable pet-free boutique building with only 18 units is just a three block walk to the white-sand beaches of the Gulf of Mexico.Fully renovated and decorated...
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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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6 bedrooms; 4 full bathrooms; sleeps 14 Luxury home in desirable Old Naples. Nestled in the heart of Old Naples, 75 yards to the beach 2 blocks from shopping / restaurants (Fifth Ave South / Third Street), this professionally decorated private oasis is the perfect setting for your family or corporate...
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We had all the comforts of home & the pristine beach just seconds away. We had beautiful accommodations & everything we needed. Our family had a wonderful vacation with plenty of space for our group of...
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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...
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The Coconut Plantation is the pinnacle of Naples luxury living. Prepared to be enchanted upon arrival as you are greeted by a lush landscape. Royal Poinciana frame this plantation style house that overflows with southern charm. A brick paver circular driveway provides the gateway to this southern style...
Distance to beach: 0.7 miles to Olde Naples Beach Access
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DEC 20th, JAN, FEB, MAR, APR 2026 available! We still have this and other homes available through Apr 2026. Call or inquire for details.ALL INCLUSIVE monthly rate May to Dec 19th $3,800. Dec 20th to Apr $5,500 (rent, tax, cleaning, utilities, cable/WIFI, damage waiver all included). Naples FL vacation...
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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...
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Welcome to the Cypress House!Professionally decorated 3 bedroom and 2.5 bathroom home in the heart of Old Naples. The Cypress is on a quiet mahogany tree-lined street just a short walk to the beautiful beaches and refreshing waters of the Gulf of Mexico as well as popular dining, shopping, and the...
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Never miss a sunset from this beautifully appointed beach house, located just steps from Naples Famous Pier and beautiful white sand beaches, this home's location can't be beat! A luxurious luxury home with all the bells and whistles. Enjoy sunsets from the rooftop deck or stroll down to the...
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This finely decorated home is the pinnacle of luxury Old Naples living. The Balmoral has five bedrooms and plenty of living space, with tall ceilings and large windows for tons of light. The open living room and kitchen layout overlooks sliding glass doors that lead directly to the pool. The pool area...
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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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A rare opportunity located in the heart of Old Naples at $55,000/month in season. This three-level residence offers simple and crisp spaces, creating a seamless flow from room to room with white limestone floors, imported Italian wood and glass custom doors and custom cabinetry in the kitchen and baths....
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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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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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Welcome to an exquisite abode at 380 4th Avenue South, Unit 380, nestled in the heart of scenic Naples, FL. This tastefully appointed residence offers 1,000 square feet of thoughtfully designed living space. Delight in two elegantly crafted bedrooms and two pristine bathrooms, all enhanced by central...
Distance to beach: 0.9 miles to Naples Beach
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This spacious 2-Bedroom Suite includes a king-size bed in the primary bedroom, two twin beds in the secondary bedroom, a sleeper sofa in the living area, a screened lanai and a kitchen. Fully-equipped kitchens include a coffee maker, refrigerator, oven, microwave, stovetop and toaster. Each Suite also...
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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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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
Our stay in old town Naples could not have been any better. Great location, just a couple of blocks from the 5th Ave action. Condo includes a wonderful heated pool just out the front door. The charming...
Distance to beach: 30 yards to Naples beach
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Old Naples is renowned as the most enchanting part of Naples, inhabited by the healthiest, happiest, most content, and most laid-back residents in the country. Indeed, life is, splendid on the Paradise Coast. Feel free to contact the owner with any questions you may have !!! Old Naples serves as a...
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2 Bedroom, 1.5 bath condo on 2nd floor. Walk in shower, bedroom 1 has queen bed, bedroom 2 has 2 twin beds. Living room has 50” smart TV with Wi-Fi included. Fully equipped kitchen with granite countertops. Screened lania with table and chairs. Assigned parking spot near stairs, also has quest parking....
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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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Completely remodeled unit in a quaint, lush courtyard-style community. This condo is furnished and decorated as if it was your 2nd home. French Oak floors throughout the living and bedroom areas, walk in showers with high end finishes, instant water heater for never ending hot showers, fully furnished...
Known for its historical homes and tropical landscaping, Old Naples is a quiet neighborhood in the stunning city of Naples. Our vacation rentals put you close to shopping, golf courses, and residential amenities so you can have the trip of a lifetime.
World-Class Beaches: Old Naples rentals is home to a 10-mile beach with nearly two dozen public access points. Avoid the parking fiasco by staying right where you want to be.
History: Close to the historic Naples Pier and Naples Historical Society, you can learn more about the history and culture of a city that dates back to the 1800s.
Culture: Visit one of the many fine art galleries in Naples or check out the 170-acre Naples Botanical Garden.
Opulent Rentals: Known as one of the most exclusive communities on the coast, Old Naple rentals range from 1 to 7 bedrooms. Many of these historic vacation homes are a destination in their own right.
Convenient Location: Old Naples puts you close to restaurants and boutiques on 3rd Avenue and 5th Avenue Beach for a little luxury and excitement.
Unforgettable Views: The pristine sands of Naples Beach are worth the visit, whether you see them from the shore or out on the waters. Walk, bike, or swim along the coast, or charter a boat to see some dolphins at play.
Family-Friendly Amenities: Available rentals with granite kitchens, gourmet kitchens, beach views, fireplaces, and security systems make it easy to find the place for you and your loved ones.
There's nothing quite like finding the perfect location on the Gulf Coast. If you love the city of Naples but also want a little peace and quiet, Old Naples helps you strike just the right balance.
Whether you lounge in your vacation home for your trip or just use it as a home base, book a vacation rental in Old Naples for a trip you won't soon forget.
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