Winter Rentals in Naples

There are a lot of options in Naples. If you plan on staying in the Naples area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Naples:

• Charming Beach Cottage with private Pool&Spa! Walk to stunning Vanderbilt Beach
• Relax by the sand at nearby Vanderbilt Beach or hang by heated pool
• Apollo 603-Remodeled!
• Holiday Winter Sale Hemingway House Marco Island Last Minute Discount Book ASAP
• 🐬 Beachfront Newly Remodeled Apollo Condo on 9th Floor with great Ocean Views!
• Exclusive Jan–May Special Naples Pool Home Walk to Beach & Mercato
• Great Beach Views, Direct Access, Pickleball, New Kitchen & Heated Pool! Tower 3
• SEASON SPECIALS! Designer House, Heated Pool & Spa, close to beaches, FREE Bikes
• Walk to Beach, Restaurants, Shops, Movies. Water Front, Large Heated Pool, Dock
• Special Offer! Limited-Time Deal Walk to Beach Heated Pool & Spa

The average cost for winter rentals in Naples is $489 per night. Allinclusivebeachresorts has a wide list of great winter places to stay near Naples that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Yes, here are the top cottage/chalet rentals in Naples that allow you to bring your pet or dog:

• Charming Beach Cottage with private pool! One mile to stunning Horizon Beach!
• 978 Spruce Avenue
• Marco Island Home w/Hot Tub, Lanai & Yard
• Waterview 3 ensuite home with pool nHGTV chose as ideal vacation home!

See all pet-friendly vacation rentals in Naples on Allinclusivebeachresorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Naples to find what works for you.

As of 2026, the data from Allinclusivebeachresorts shows that there are over 9775 private swimming pools or indoor pools accommodations near Naples along with other great amenities.