Discover winter rentals South Maui - We found 4965 exact matches
About South Maui Winter Rental on Hawaii.Villas
Planning a winter vacation in South Maui? Discover 4965 places to stay, ideal for family trips, group getaways, or wedding retreats.
At HawaiiVillas, explore a wide range of accommodations in South Maui, HI perfect for your winter escape. Our listings feature private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, all equipped with top amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Winter accommodations in South Maui start at US $605, with popular options including cabins, bungalows, and privately owned rental homes. Planning a snowboarding adventure? We offer numerous snowboard-friendly ski resorts, chalets, and cabins available for short-term or extended stays, whether for a weekend getaway or a longer retreat.
HawaiiVillas provides great deals for travelers seeking rentals in South Maui. To secure your winter vacation home, visit HawaiiVillas, use our filter options to specify your travel dates, property type, and desired amenities. Choose from a comprehensive list of winter vacation rentals hassle-free. Explore our interactive map to discover all lodging options in and around South Maui and unlock exclusive deals.
Frequently Asked Questions About South Maui Winter Rentals
What are the top rated Winter Rentals in South Maui?
There are a lot of options in South Maui. If you plan on staying in the South 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 South Maui:
- 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
- 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
- Highest Guest Rating at Mana Kai, Best Ocean Views, Luxury Amenities, Ocean End
How much does it cost to rent a place to stay near South Maui in the wintertime?
The average cost for winter rentals in South Maui is $605 per night. Hawaii.Villas has a wide list of great winter places to stay near South Maui that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in South Maui that allow pets?
Yes, here are the top cottage/chalet rentals in South Maui 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 South Maui on Hawaii.Villas
Do you have any winter rentals in South Maui that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in South Maui to find what works for you.
Are there winter accommodations in South Maui that have indoor swimming pools?
As of 2026, the data from Hawaii.Villas shows that there are over 4965 private swimming pools or indoor pools accommodations near South Maui along with other great amenities.
Do any winter holiday rentals in South Maui have hot tubs?
About 4965 holiday rentals in South Maui boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in South Maui?
Yes, there are many luxury places to stay in South Maui for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near South Maui with all the best amenities for your next trip.
