Maui Winter Rentals & Holiday Homes

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

• HOKULANI 436-CORNER UNIT 2BD/2BA w/OCEAN & MOUNTAIN VIEWS,505SQFT LANAI BALCONY
• 10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
• Dazzling Ocean View, Modern, Whole house AC. Upgraded Glass for a quiet setting
• Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014
• 10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
• Stunning Views from only double lanai Penthouse unit.
• SLEEP NUMBER BED! #759 1bdrm-A Guest Favorite-Ocean/Beach View w/XBOX & ROKU!
• nRead Our Reviews and See Why Our Guests Love to Stay with Us.
• Mountain to Ocean Views Pole House @ Maui Adventure Villa
• The Whaler! ~Beautifully remodeled ground floor courtyard studio~

The average cost for winter rentals in Maui is $931 per night. Ownerdirect has a wide list of great winter places to stay near Maui 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 Maui that allow you to bring your pet or dog:

• Spectacular luxury , modern oceanfront condo Maalaea-Kihei ,Maui
• Maui Resort Rentals: Honua Kai - 6th Floor 7BR Penthouse Retreat w/Stunning Ocean Views!
• Modern & Polished Oceanfront Vistas
• Maui Home Lahaina

See all pet-friendly vacation rentals in Maui on Ownerdirect

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

As of 2026, the data from Ownerdirect shows that there are over 12473 private swimming pools or indoor pools accommodations near Maui along with other great amenities.