Shops at Wailea Winter Rentals & Holiday Homes

Discover winter rentals Shops at Wailea - We found 3201 exact matches

About Shops at Wailea Winter Rental on Rent By Owner

Planning on a winter vacation in Shops at Wailea? Discover 3201 places to stay in Shops at Wailea, for those traveling with their family, friends, in groups, or for a wedding retreat.

At Rent By Owner, we have a wide range of listings for accommodations in Shops at Wailea, HI that are perfect for your winter trip or seasonal escape. Our listings have private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that you would love. RBO winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Shops at Wailea winter accommodation starts at ZA R11,139, and the most popular properties in Shops at Wailea are cabins, bungalows, and rental homes by owner. Planning snowboarding on your next winter vacation? We have many snowboard-friendly ski resorts, chalets, and cabins that are available for you to rent. These rentals are available for both short-term stays and long-term stays, whether you are traveling for a weekend, monthly, or a longer stay, RBO will make your winter trip memorable.

Rent By Owner offers a great deal for travelers planning on renting a place in Shops at Wailea, to enjoy these benefits and to book your winter vacation homes, go to RBO filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of our winter vacation rentals without hassle. Our interactive map is also available, to view all places to stay in or around Shops at Wailea and unlock even more amazing deals.

Show more
Show less

Frequently Asked Questions About Shops at Wailea Winter Rentals

There are a lot of options in Shops at Wailea. If you plan on staying in the Shops at 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 Shops at Wailea:

The average cost for winter rentals in Shops at Wailea is $645 per night. RBO has a wide list of great winter places to stay near Shops at Wailea 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 Shops at Wailea that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Shops at Wailea on Rent By Owner

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Shops at Wailea to find what works for you.
As of 2025, the data from Rent By Owner shows that there are over 3201 private swimming pools or indoor pools accommodations near Shops at Wailea along with other great amenities.