Wailea Winter Rentals & Holiday Homes
Discover winter rentals Wailea - We found 1237 exact matches
About Wailea Winter Rental on Hawaii.Villas
Planning a winter vacation in Wailea? Discover 1237 places to stay, ideal for family trips, group getaways, or wedding retreats.
At HawaiiVillas, explore a wide range of accommodations in Wailea, 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 Wailea start at US $1,075, 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 Wailea. 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 Wailea and unlock exclusive deals.
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Frequently Asked Questions About Wailea Winter Rentals
There are a lot of options in Wailea. If you plan on staying in the Wailea area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Wailea:
- Romantic, Luxury, Sensual Retreat - Couples Only
- Luxury Cottage w/Private Pool. Under The Warm Maui Sun Pmt #BBKM20160004
- Aloha Kai Suite at Wailea Beach Villas. Penthouse 205. Ocean View. 3 BR/3 BA
- Owner Direct - Check our 160 Reviews! - Elua Village 701, Luxury 2BR, Ocean View
- 🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈
- nNEW KITCHEN REMODEL! Amazing View!
- Very Best Deluxe Ocean View.Panoramic View.First Class!
- Featured on A&E's Vacation Rental Potential! Luxury Family Condo! AC and Pool!
- 125+ 5star REVIEWS SAYS IT ALL! All upgraded/vaulted ceil/Golf & Ocean view!
- The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!
- Hawaiian Cottage and Personal Paradise/BBKM 2013/0004
- Ho'olei at Grand Wailea
- Grand Champions Condos by KBM
- Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
See all pet-friendly vacation rentals in Wailea on Hawaii.Villas
About 1237 holiday rentals in Wailea boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
