Olde Naples Seasonal Rentals & Homes for Sale

Olde Naples is the historic heart of Naples, Florida: palm-lined streets that run straight to the Gulf, with Fifth Avenue South and Third Street South a short walk from your front door. Naples Homes and Rentals offers luxury seasonal rentals and homes for sale throughout Olde Naples, with local brokers who know every block.

Whether you want a winter season steps from the beach, a home to buy, or an income property to add to your portfolio, we can help you find the right fit.

• The beach at the end of every street. The avenues in Olde Naples run west to the Gulf of Mexico, many ending in public beach access. Sunset on the sand is a nightly ritual here.
• Fifth Avenue South. Naples’ unofficial Main Street since the 1920s, lined with restaurants, boutiques, galleries and live performances.
• Third Street South. The quieter, historic sister district, with dozens of shops, cafés, galleries and a popular Saturday morning farmers market.
• The Naples Pier. The neighborhood’s best-known landmark and a favorite spot for sunrise walks, sunsets and dolphin watching.
• Cambier Park and Naples Bay. Tennis, concerts and green space just south of Fifth Avenue, plus waterfront dining and boating along the bay.

Homes range from restored Old Florida cottages to new estate homes and downtown condos, often on the same street. That mix gives Olde Naples its relaxed, unpretentious character.

Olde Naples rentals are booked by the month, most often for the winter season from January through April. Within the City of Naples, residential rentals generally must be 30 days or longer, so our Olde Naples homes are offered as monthly seasonal rentals rather than nightly stays.

Our current Olde Naples rentals include:

Olde Naples is one of the most sought-after addresses in Naples. Buyers pay a premium for being within a few blocks of the beach, Fifth Avenue South or Third Street South, and lots that come to market rarely last long.

We help buyers compare properties block by block: distance to the beach, walk time to Fifth Avenue, lot size, flood zone, and whether a home is suited to renovation or new construction. See Naples homes for sale.

There is no official boundary for Olde Naples, and brokers draw it differently. Most consider it the area around the Naples Pier, Fifth Avenue South and Third Street South, from about 7th Avenue North south toward 14th Avenue South, between the Gulf and Naples Bay.

To the south are Aqualane Shores and Port Royal, two of Naples’ most exclusive waterfront communities.  To the north is the Park Shore and Coquina Sands area.

Managing Broker Michelle Craft and Associate Broker Patricia Moreno-Morello have helped renters, buyers and investors in Olde Naples for years. Tell us what you are looking for and we will send you options that match.

Can I rent a home in Olde Naples for less than a month?

Generally no. Within the City of Naples, residential rentals must normally be 30 days or longer, with a property allowed only three shorter rentals per year. That is why Olde Naples homes are offered as monthly seasonal rentals.

When is the best time to book an Olde Naples seasonal rental?

As early as possible. The winter season, especially January through April, is the most in-demand time, and many guests reserve the next season before they leave in spring.

Where is Olde Naples?

Olde Naples is the historic downtown area of Naples, Florida, around Fifth Avenue South, Third Street South and the Naples Pier. It runs roughly from 7th Avenue North south toward 14th Avenue South, between the Gulf of Mexico and Naples Bay.

Is Olde Naples walkable?

Yes. It is one of the most walkable neighborhoods in Naples. The beach, restaurants, shops, galleries and parks are all within walking or biking distance of most homes.

Is Olde Naples a good place to buy a rental property?

Olde Naples has strong seasonal rental demand, and many owners use winter rental income to offset carrying costs before they retire to Naples. Rental rules, HOA restrictions and location all affect returns, so talk with a local broker before you buy.

What is the difference between Old Naples and Olde Naples?

They are the same neighborhood. Both spellings are commonly used for the historic area around Fifth Avenue South, Third Street South and the Naples Pier.