Kihei Winter Rentals & Holiday Homes

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

• 10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
• Breathtaking ocean views! Steps to the beach! Recently remodeled!
• Dazzling Ocean View, Modern, Whole house AC. Upgraded Glass for a quiet setting
• 10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
• Stunning Views from only double lanai Penthouse unit.
• 5-Star Reviews! All Remodeled! Split Air! Quiet Building 5! Ocean/Garden View!
• Hotel-zoned Oceanfront Comfort on a Budget 2bed 2ba condo - NEW LISTING!
• Bingo! KKN's TROPHY Unit! Deluxe Renovation, Central Split A/C & Ground Floor.
• Maui Paradise – BEACH FRONT condo w/AC, Stunning Ocean & Sunset Views!
• 200+ 5 Star Reviews, Premier Front-Row Sunset Views,1 Of Largest Spacious Condos

The average cost for winter rentals in Kihei is $587 per night. Travelthehorizon has a wide list of great winter places to stay near Kihei 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 Kihei that allow you to bring your pet or dog:

• Ocean, mountain, pool views. Best location at The Banyan. Across from Kam2 beach
• Kihei Maui Island Style, Beach, Pool, Restaurants Kihei Gardens Estates
• Modern & Polished Oceanfront Vistas
• Ocean Front Penthouse Best View Most Amenities Fully Stocked Feels like home

See all pet-friendly vacation rentals in Kihei on Travelthehorizon

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

As of 2026, the data from Travelthehorizon shows that there are over 5054 private swimming pools or indoor pools accommodations near Kihei along with other great amenities.