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245 Broad Ave S Naples
A slice of Key West HEAVEN in the HEART of Olde Naples. Affectionately called "The Christmas Cottage," this Craftsman SFH is luxurious and lavish, yet as comfortable as your home. A very upscale main house…
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187 Broad Ave S Naples
Everything you dream about in this remastered Olde Florida cottage. Pet Friendly. 1.87 blocks to the Beach. 1.87 blocks to Campiello's and Tommy Bahama's ... and all that is fabulous dining and shopping. Main house…
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287 11th Ave S Naples
Newly restored + luxuriously to the NTH Degree. Absolutely everything you dream about in a Naples vacation rental is contained within the walls of the updated Old Glory Cottage and Guesthouse located in the Olde…
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175 8th Ave S Naples
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…
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675 2nd St S Naples
Beautiful and elegantly appointed, be the first to enjoy this 4 bedroom, 4.5 bath house in Olde Naples, just 2 blocks to the beach. The living room offers a neutral-toned l-shaped, linen couch, side chair,…
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154 4th Ave N Naples
Coastal Chalet in Olde Naples - this stunning coastal dream is only a 2-min walk to the sparkling coastline of the Gulf of Mexico! This beautifully appointed home includes 4 bedrooms (two of them being…
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160 Broad Ave S Naples
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…
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613 14th Ave Naples
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 sprawling plantation style house that overflows with…
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380 5th Ave N Naples
Experience life in one of Naples' most pleasant neighborhoods just steps to the beach! Southern Sunset is a newly renovated and designer decorated coastal style home with all of the features and amenities you're searching…
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329 2nd Ave N Naples
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…
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134 16th Ave S Naples
CHARMING OLD NAPLES. Just STEPS from the beach & a quick walk to the 3rd Street shopping/dining district, this completely remodeled (2023) home retains its vintage charm. From the high ceilings and clerestory windows…
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642 6th Ave N Naples
Escape to this stunning Olde Naples retreat, perfectly located on a beautiful tree-lined street just blocks from the beach, parks, and the vibrant dining and shopping of Fifth Avenue South and Third Street. Designed for…
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300 2nd Ave N Naples
BOOKED FROM JAN. 1- April 30, 2026'. This furnished house, designed by MHK Architect, is perfectly situated just 2 blocks to the beach and a short stroll to Fifth Ave. Open floor plan with 370…
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434 3rd Ave S Naples
Arguably the best location for a rental in Olde Naples! Only 3 blocks from the white sandy beaches that make Naples one of the most desired locations in FL. This dream home boasts nearly 5,000…
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63 13th Ave S Naples
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…
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85 13th Ave S Naples
Never miss a sunset over the Gulf of Mexico from this beautiful beach house, close to our famous Naples pier and beautiful white sand beaches. This home is located on the same block as the…
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140 2nd Ave S Naples
This newly renovated home is centrally located to the best Old Naples has to offer. Only a block from the beach, and a short walk to Fifth Avenue's luxurious restaurants and shops, so you're right…
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194 4th Ave N Naples
The annual rate is $36,000.00 / month. The advertised rate is for high-season (Nov.-April); longer terms have greater discounted rates. Situated only four houses from Naples’ sugar sand beaches on an oversized lot offering the…
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888 10th Ave S Naples
Enjoy the heart of Olde Naples in fantastic 888 10th Ave S! The home features four bedrooms in the main house and a separate private guest cabana above the garage. This spacious floor plan can…
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783 11th Ave S Naples
This exquisite 4 bedroom, 5 bathroom coastal contemporary home is perfectly situated just blocks from Naples’ white sand beaches and the vibrant Third Street South and Fifth Avenue districts. Built in 2022, the 4,600-square-foot retreat…
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