Search all Listings
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…
Details
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…
Details
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,…
Details
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…
Details
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…
Details
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…
Details
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…
Details
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…
Details
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…
Details
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…
Details
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…
Details
165 Broad Ave S Naples
This remarkable home is only one block away from the beach and walking distance to all that the heart of Naples has to offer, including the beach, Third Street South, and 5th Avenue. This home…
Details
221 2nd Ave N Naples
Annual rate is $40,500 per month. Listed rate is for High Season (Nov. through April). Longer High Season leases have greater discounted rates. See attached rate sheet. Located only two blocks to the beach and…
Details
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…
Details
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…
Details
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…
Details
982 9th Ave S Naples
Just minutes from the charm of 5th Avenue South, 3rd Street South, and the sparkling waters of Naples Bay, this modern three bedroom, four bath home is your private winter sanctuary. From the moment you…
Details
362 2nd Ave N Naples
A welcoming Olde Naples retreat awaits at Neapolitan Sky! The stately Key West style home sits amidst lush landscaping on one of the prettiest tree-lined avenues in town, just a third of a mile from…
Details
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…
Details
687 9th Ave S Naples
687 9th Ave S is a short distance to fabulous dining on 5th Avenue, shopping on 3rd Street South, tennis and other fun at Cambier Park, relaxing at the Naples Beach, and boating on Naples…
Details