Kaanapali Winter Rentals & Holiday Homes
Discover winter rentals Kaanapali - We found 2798 exact matches
About Kaanapali Winter Rental on Hawaii.Villas
Planning a winter vacation in Kaanapali? Discover 2798 places to stay, ideal for family trips, group getaways, or wedding retreats.
At HawaiiVillas, explore a wide range of accommodations in Kaanapali, 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 Kaanapali start at US $1,514, 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 Kaanapali. 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 Kaanapali and unlock exclusive deals.
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Frequently Asked Questions About Kaanapali Winter Rentals
There are a lot of options in Kaanapali. If you plan on staying in the Kaanapali area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Kaanapali:
- HOKULANI 436-CORNER UNIT 2BD/2BA w/OCEAN & MOUNTAIN VIEWS,505SQFT LANAI BALCONY
- SLEEP NUMBER BED! #759 1bdrm-A Guest Favorite-Ocean/Beach View w/XBOX & ROKU!
- The Whaler! ~Beautifully remodeled ground floor courtyard studio~
- Maui Resort Rentals: Hokulani 605 – Premier 6th-Floor Oceanview Penthouse | Closest 2BR Column to the Ocean!
- Honua Kai 825 3BD Oceanfront Retreat w/Lanai, Floor-to-Ceiling Views & Modern Kitchen
- The Whaler 814, Black Rock, All 5 Stars
- Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!
- Maui Resort Rentals: The Whaler 1015 - Gorgeously Remodeled 10th Floor Interior Courtyard Studio, Spectacular Ocean and Mountain Views!
- EASTER SPECIAL 250+BEACHFRONT RESORT+OCEAN VIEW+A317+CENTRAL A/C+FULLY EQUIPPED+
- Ocean View Studio #264 - Open between May 9-21, 2026 - 7 night minimum required
- Exquisite Condo with an Awesome Ocean View Emerald 289
- Maui Kaanapali Villas B225
- Whaler Resort by KBM
- WOW- New 2bd/2ba, Largest Lanai w/Ocean & Golf Course Views, Lowest Resort Fee!
See all pet-friendly vacation rentals in Kaanapali on Hawaii.Villas
About 2798 holiday rentals in Kaanapali boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
