Wailea Hotels with a Pool

Hotel search

Get Secret Prices on select hotels

These prices aren’t available to everyone.

Deal of the day

See all 164 Wailea deals

Pay now or later on most rooms

Free cancellation on most rooms

Price Guarantee

Hotels in Wailea with a Pool

With Hotels.com, you can book a hotel with a pool in Wailea for as low as $174 per night.

A quiet, serene pool is a fantastic way to get away from the daily stresses of life and finally relax on your trip. Heading down to the pool can be also be a refreshing way to get some exercise on your trip besides hitting the hotel gym. Stay warm any time of year at an indoor pool, or soak up the sun at our hotels featuring outdoor pools.

If you're traveling with kids in Wailea, the pool can be a handy way to keep them active and entertained. Lounge around and stay dry, or get out and go swimming with the whole family.

Can't decide which accommodation works best for you? We recommend you explore the complete selection of hotels in Wailea by further narrowing down the list by star ratings, price, or using the map to find how hotels near top attractions. Be sure to check each property for any specific amenities you may enjoy during your stay, such as a hot tub, infinity pool, or poolside bar.

Here's a quick overview of what our verified guests have rated as the best free breakfast hotels for:

  • Cleanliness: Wailea Beach Villas, A Destination Luxury Hotel
  • Service: Four Seasons Resort Maui at Wailea
  • Comfort: Ho'olei at Grand Wailea
  • Condition: Ho'olei at Grand Wailea

Rest assured, no matter where you’re traveling, Hotels.com has a great deal for you. So pack a swimsuit and have a great trip!