Naples’ winter season runs December through April, and the best seasonal homes are reserved months ahead. Naples Vacation Properties manages more than 100 homes and condos across Olde Naples, Park Shore, Vanderbilt Beach and beyond — including a curated collection available for monthly, seasonal, and 30-day+ stays. Browse what’s available for your dates below, or call our local team at (239) 206-3375 and we’ll match you with the right home.
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Guests Winter Seasonal Rentals in Naples (December–April)
Every winter, Naples fills with seasonal residents escaping the northern cold — and the homes they stay in are typically booked the previous summer and fall. Most of our seasonal and winter rentals require a 30-day minimum stay, with the strongest selection for guests who reserve between August and October. If you’re planning a snowbird season in Naples, now is the time to lock in your home: January–March inventory tightens quickly, and the most requested neighborhoods go first. New to wintering in Naples? Our snowbird guide to booking a winter rental walks through the whole process, and our guide to Naples in January shows what peak season feels like. Budgeting your stay? Our guide to what a seasonal rental in Naples costs breaks down real 2026–2027 pricing, and our overview of when season runs in Naples covers the timing.
Where Winter Guests Love to Stay
Walkable Olde Naples puts Fifth Avenue South dining and the beach at your doorstep. Park Shore and The Moorings offer quiet, established neighborhoods minutes from the Gulf. Vanderbilt Beach and Pelican Bay pair beach living with easy access to Mercato’s shops and restaurants, while golfers gravitate to Treviso Bay, where select rentals include TPC golf privileges. Want more space near the beach? Naples Park offers single-family homes — many with private pools — a short golf-cart ride from Vanderbilt Beach.
Monthly & Long-Term Rentals Year-Round
Beyond the winter season, we offer monthly rentals and extended stays throughout the year — ideal for relocations, home renovations, extended workcations, or simply a slower pace of Naples living. Many homes also offer 90-day and annual lease options; use the filters above to see them.
Why Book Direct with Naples Vacation Properties
We’re a locally owned vacation rental and property management company — not a national chain. Booking direct means no third-party service fees, straight answers from a team that knows every home personally, a 4.8-star Google rating, and an A+ BBB rating backing it up. Our office is right here on Tamiami Trail, and we’re on call throughout your stay.
Seasonal Rental FAQs
What is the minimum stay for a seasonal rental in Naples?
Most seasonal and winter rentals require a 30-day minimum stay, which is set by each community’s rules. A few communities allow shorter stays — our team can point you to them.
When should I book a winter rental in Naples?
For January through March stays, reserve by early fall. Returning guests often rebook the same home for the following winter before they leave, so the best homes rarely reach the open market.
Are utilities and Wi-Fi included?
Our seasonal rentals come fully furnished, and utilities and Wi-Fi are typically included — we confirm the details for your specific home in writing before you book.
Do you have pet-friendly seasonal rentals?
Yes — a hand-picked collection. Pet-friendly homes are the scarcest inventory in town for winter stays, so start with our pet-friendly rentals and book early.
Can I extend my stay?
Often, yes — subject to the home’s availability. Tell us up front if you might extend and we’ll flag homes with open calendars around your dates.
Ready to plan your winter in paradise? Browse the seasonal rentals above, or call (239) 206-3375 to talk through your dates with our Naples team.