Kauai Winter Rentals & Holiday Homes

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

• Romantic & Breathtaking Oceanfront Kauai Condo
• Hawaiian Charm.Just Steps From The Ocean.On Kauai's Sunny W Side * TVNC4216
• Stunning 2 Bedroom Luxury Cottage 300 feet from Poipu Beach Park
• Spring Specials!, Wkly Disc. & Promos 5 star Reviews! F403 Top Floor 2 BR/3 BA
• Poipu Bay Getaway - Poipu House - Saltwater pool, hot tub, AC!, Walk to Beach and Hyatt!
• Charming Anahola Studio Cabin ~ Short Walk to Beach
• Top Floor Penthouse Ocean & Pool View 2 Cal King Beds Best Reviews In Waipouli
• 100% Renovated Luxury Condo with Ocean/Jungle/Mountain/Waterfall Views
• Mid-century Remodeled Spectacular Ocean Views! 10% Discount for Week+ Stays!
• OCEANFRONT Ground Floor 2bd/2ba Unit with Amazing Ocean Views & A/C

The average cost for winter rentals in Kauai is $816 per night. Outdoorplaces has a wide list of great winter places to stay near Kauai 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 Kauai that allow you to bring your pet or dog:

• Lani Kai home
• Fully Renovated Oceanfront with Air Cond. Ground Floor Unit with Spacious Lanai!
• H302 - Stunning Ocean View Corner Suite at The Waipouli Beach Resort - Sleeps 4
• Hale Moli home

See all pet-friendly vacation rentals in Kauai on Outdoorplaces

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

As of 2026, the data from Outdoorplaces shows that there are over 5298 private swimming pools or indoor pools accommodations near Kauai along with other great amenities.