Naples Vacation Properties is a locally owned vacation rental company managing 100+ hand-picked luxury rentals across Old Naples, Park Shore, Pelican Bay, Vanderbilt Beach, the Moorings and North Naples — from bay-view condos to beachfront estates. Every home is managed by a team that lives and works in Naples, and guests have made us the most-reviewed boutique rental agency in town: 4.8 stars across 84+ Google reviews, with an A+ accreditation from the Better Business Bureau. Whether you’re planning a week on the sand or a full winter season, this page is the place to start.
What makes a Naples rental “luxury”?
In Naples, luxury is location first: walkable Old Naples streets, private beach access, bay and Gulf views. From there it’s the home itself — designer furnishings, heated pools, chef-ready kitchens, hotel-grade linens — and finally the service around it. Our standard covers all three. We hand-pick each property, inspect and professionally clean between every stay, and answer our own phones locally, so the concierge feel lasts from booking to checkout. No national call center, no ticket queue: the people responsible for your stay are minutes away.
Luxury rentals by neighborhood
Old Naples
The classic address. Historic streets where you can walk to Fifth Avenue South for dinner, Third Street South for the Saturday farmers market, and the pier for sunset. Our Old Naples collection ranges from renovated cottages to condos steps off the avenue. Browse Old Naples rentals.
Park Shore
Bay-front high-rises and quiet residential streets wrapped around Venetian Bay, with private beach access and the Venetian Village shops and restaurants at the center. A favorite for seasonal guests who want water views with everything nearby. Browse Park Shore rentals.
Pelican Bay
Naples’ signature amenity community: private beachfront clubs reached by tram through the mangroves, miles of walking paths, and golf and tennis at the center of it all. Our Pelican Bay condos put the full resort life inside a residential setting. Browse Pelican Bay rentals.
Vanderbilt Beach
Some of the best sand in Southwest Florida, with the Ritz-Carlton and Mercato’s dining and nightlife minutes away. Beachfront condos and newer luxury buildings dominate here — ideal for guests who want their mornings to start on the Gulf. Browse Vanderbilt Beach rentals.
The Moorings & North Naples
The Moorings offers quiet bayside living close to downtown; North Naples adds newer construction, family-friendly space and easy beach access. Both are smart picks when the season calendar fills up closer to the water. Browse Moorings & North Naples rentals.
Seasonal winter rentals — how Naples “season” works
Naples’ winter season runs November through April, with peak demand January through March. A few practical notes from a local team that lives this calendar every year:
- Book 9–12 months ahead. The most-requested homes for January–March are typically reserved by early fall, and many repeat guests rebook before they fly home.
- Expect 30-day minimums. Many Naples communities require monthly minimum stays in season; we’ll match you with the right property for a one- to four-month stay.
- Budget realistically. Seasonal winter rates across our portfolio range from about $5,000 per month for well-appointed condos to over $100,000 per month for premier beachfront estates, with peak pricing in January–March.
- Shoulder months are the value play. November, December and April offer the same homes and most of the weather at meaningfully gentler rates.
Why guests choose Naples Vacation Properties
- The deepest review base of any boutique agency in Naples — 4.8 stars across 84+ Google reviews, plus BBB A+ accreditation.
- Genuinely local. Our whole team lives and works in Naples. The person who books your stay and the person who answers mid-stay questions are neighbors, not a call center.
- Hand-picked portfolio. 100+ homes and condos make the cut — we manage properties we’d stay in ourselves, and it shows in the reviews.
- Full-service stays. Professional cleaning, quality linens, equipped kitchens, fast local support, and help matching the right home to your dates, group and budget.
Frequently asked questions
How much does a seasonal winter rental in Naples cost?
Seasonal winter rates across our portfolio range from about $5,000 per month for well-appointed condos to over $100,000 per month for premier beachfront estates. January through March is peak pricing; November, December and April typically offer better value on the same homes.
How far in advance should I book for January–March?
Nine to twelve months. Our most-requested seasonal homes are typically reserved by early fall, and many repeat guests rebook for the following winter before their current stay ends.
Which Naples neighborhoods do you cover?
Old Naples, Park Shore, Pelican Bay, Vanderbilt Beach, the Moorings, North Naples and Treviso Bay — 100+ hand-picked luxury homes and condos across the areas visitors ask for most.
Do you offer monthly or seasonal (30-day+) rentals?
Yes — seasonal winter stays are our specialty. Many Naples communities have 30-day minimum-stay rules, and we’ll match you with the right property for a one- to four-month stay.
Are your rentals pet-friendly?
Some of our homes welcome pets and some do not. Use the pet-friendly filter on our website, or tell our team you’re traveling with a pet and we’ll match you with the right home.
What’s included in a stay?
Every home is professionally cleaned and fully furnished with linens, towels, wifi and an equipped kitchen, and our local Naples team is on call throughout your stay. Extras vary by home — ask us about beach gear, pool heating and check-in timing for your dates.
Start planning your Naples winter
Tell us your dates, group size and must-haves, and a local specialist will shortlist the right homes — or browse the full portfolio now. Call (239) 206-3375. Season fills fast; the best of Naples goes first.