A season spent where the beach, Fifth Avenue South and the pier are all on foot.
Olde Naples is the address most seasonal visitors want and the one that books first, because everything that brings people to Naples in February is inside a few walkable blocks. Inventory is furnished condominiums and houses released by their owners for the winter, and the good ones tend to go to the same guests year after year.
Olde Naples Vacation Rentals at a Glance
| Where | Olde Naples — 7th Avenue North to 13th Avenue South, west of US-41 |
| Season | January through April, peaking in February; a shoulder market either side of it |
| Typical Stay | By the month or the season rather than the week; a thirty-day minimum is the common arrangement |
| Property Types | Furnished condominiums in small low-rise buildings, beach-block cottages and larger single-family homes |
| On Foot | The beach, Fifth Avenue South, Third Street South, Crayton Cove and the Naples Pier |
| Booking Window | Peak months are often committed six to twelve months ahead; the best residences re-let before they are advertised |
| Rules | Olde Naples sits inside the City of Naples, which regulates short-term rentals more tightly than the county; terms vary by district and by association |
| Management | Alpizar Property Management, with an in-house team for furnished seasonal rentals |
Olde Naples Vacation Rentals - Active Listings
Request the Olde Naples Seasonal List
A good deal of the best seasonal inventory here never reaches a portal, because it is re-let privately before it needs to. Tell us your dates, your party and the block you have in mind, and we will send what is genuinely available, including residences held back for returning guests.
What a Season in Olde Naples Looks Like
Mornings on a beach reached in a few minutes on foot, afternoons on Third Street South, dinner on Fifth Avenue South and the walk home afterwards rather than a drive. It is a compact, low, tree-lined grid, and guests who rent here tend to leave the car parked for days at a time — which is precisely why they come back to the same few streets. February is the peak of it, and the month people plan a year in advance.
How Renting Works Here
Seasonal residences are let on a written lease for a month or more, usually furnished and equipped down to the linens, with utilities and internet included. Expect an association application, a modest application fee and an approval step in a condominium, a security deposit in every case, and taxes added on stays of six months or less. Reserving peak months generally means a deposit well in advance and a balance due before arrival. We handle the paperwork and the association approval rather than leaving you to it.
A Condominium, a Beach Block Cottage, or a Larger Home
A furnished condominium is the simplest and most common way to take a season here, and in the small buildings near Gulf Shore Boulevard South it puts the beach minutes from the door. A house on the Beach Block suits families and multi-generational groups who want a pool, a garage and outdoor space, and larger homes accommodate the households who arrive with everyone in tow. If a wide Gulf horizon from a high floor matters more than the walk to Fifth Avenue South, look at beachfront rentals elsewhere along the coast, or the whole of Naples vacation rentals, and we will compare them honestly against Olde Naples.
Annual Rentals
Year-round leases in Olde Naples are uncommon, because an owner can earn in one season much of what a full year would pay. When one does appear it is usually arranged quietly, so if you need a twelve-month home in the neighborhood, request a list and we will tell you as they surface; otherwise Naples annual rentals covers the wider market.
Own in Olde Naples? Let Us Manage Your Vacation Rental
Alpizar Property Management handles furnished seasonal rentals with an in-house team, from marketing and guest screening to association applications, turnover cleaning, maintenance and monthly statements. An Olde Naples residence let well through the winter can carry much of its own cost. Tell us about your property and we will outline what it should earn.
Explore Olde Naples
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Olde Naples Vacation Rental Questions
What is the minimum stay for a vacation rental in Olde Naples?
Most owners and associations here let by the month rather than the week, and a thirty-day minimum is the common arrangement. Olde Naples sits inside the City of Naples, which regulates short-term rentals more tightly than the county does, and the terms vary by zoning district and by association — we confirm what applies to a specific address before you book.
When should I book a season in Olde Naples?
Early. Season runs January through April and peaks in February, and the better residences are often committed six to twelve months ahead, many of them re-let to the same guests year after year. If you want a particular building or a particular block, treat the spring before as the deadline rather than the fall.
What does a seasonal rental in Olde Naples cost?
It depends almost entirely on the month, the size and the distance to the water. January through April carries a large multiple of the off-season monthly rate, and a residence on the beach carries a further premium over one a few blocks east. Tell us your dates and we will send current rates for what is actually available.
Can I walk to the beach and Fifth Avenue South?
That is the reason most people rent here. Olde Naples is compact, and from most of it the beach, Fifth Avenue South, Third Street South, Crayton Cove and the Naples Pier are all within walking distance — many guests leave the car parked for days at a time.
Are pets allowed in Olde Naples vacation rentals?
Sometimes, and it is decided twice — once by the association and once by the owner. Pet-friendly seasonal residences are a small share of the inventory and they are taken early, so tell us at the outset rather than after you have chosen a shortlist.
Do you manage vacation rentals in Olde Naples?
Yes. Alpizar Property Management runs furnished seasonal rentals with an in-house team — marketing and guest screening, association applications, turnover cleaning, maintenance and monthly statements. Tell us about your residence and we will outline what it should earn.
Availability, rates and minimum stays change constantly and are confirmed at the time of booking. Rental regulations and association rules differ by district and by building and change over time; confirm current requirements with the City of Naples and the applicable association.
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Alpizar & Company is a family-owned independent brokerage specializing in luxury waterfront real estate across Naples' most sought-after neighborhoods. Led by Robert Alpizar (CLHMS, GRI, SRS, PSA) and Marlene Alpizar, our team operates as advisors — not salespeople — guiding buyers and sellers with firsthand local expertise and no corporate quotas.
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