Wailea-Makena Vacation Rentals

Check prices for these upcoming dates

Wailea Travel Guide

On the stunning, lush island of Maui, resort area Wailea offers beaches, shops, horseback riding, golfing, and much more.

Things to Do in Wailea

Makena Beach is perfect for swimming, snorkeling, and bodyboarding. Set in Makena Beach State Park, composed of Big Beach and Little Beach, it's a beautiful sandy stretch of shoreline. Wailea Beach is a must see with its perfect sand and blue waters that are all tucked between two green rocky points. The beach is very family friendly and ideal for sunbathing and swimming. Unmissable is one of the glorious sunsets at Keawakapu Beach; Maui sunsets are something else.

Wailea offers great trails for horse backriding on the Ulupalukua Ranch property a beautiful way to see stretches of the island at sunset or sunrise, and exploring the lush slopes to get amazing views of La Perouse Bay.

Another popular activity in Wailea is exploring La Perouse Bay and looking for Spinner Dolphins, this bay is also at one end of the historic King's Trail of Maui, a real look at ancient Hawaii in its purity.

Wailea offers golfing at the Wailea Golf Club, tennis, dinner, and live entertainment plus a luxurious spa and plenty of shops at the high-end shopping center Shops at Wailea.

Best Time to Visit Wailea

April through May and September through November are the best times to visit.

Price and Availability in Wailea

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
The cheapest day to stay at a vacation rental in Wailea tends to be Wednesday, while the most expensive day tends to be Sunday. Vacation homes in Wailea tend to be busiest on Fridays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Wailea is in December, while the cheapest month is in October. The most popular time to book a vacation rental in Wailea is in the high season in July. Wailea has its low season in September, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Wailea

Rainy days
90° 73°
0
90° 71°
1
89° 67°
0
86° 65°
0
84° 66°
1
85° 65°
1
83° 66°
1
85° 67°
0
87° 69°
0
90° 70°
0
90° 71°
1
90° 72°
0
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Wailea. The warmest months in Wailea are March and April, when temperatures reach 90 ˚F. The coolest month is January, when temperatures drop to 65 ˚F. The wettest month in Wailea is November with 1.3 inches of rain, while the driest month is May with 0.02 inches of rain.

What Expert Travelers Think

  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School
  • — AllTheRooms.com makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from

    ArtMatters.Info
    ArtMatters.InfoArtMatters.Info
  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker

Vacation Rentals in Wailea

At AllTheRooms.com we have accommodations from all of the best providers - Airbnb, Priceline, Agoda and many more. Wailea has 3,526 hotels, vacation rentals and other unique places to stay, with prices to suit careful travellers, luxury travelers and everything in between. For those trying to keep costs down, the cheapest place to stay in Wailea is only $26 a night. An average accommodation in Wailea costs on average $332 per night.

Those looking to get some work done during their trip to Wailea can choose from 631 places to stay that have WiFi. We have 17 accommodations that include a breakfast included. You can maintain your workout routine by staying at one of 131 accommodations that provide gym facilities. If you're planning on getting to Wailea by car, be sure to choose from 618 accommodations that provide parking. 573 hotels and vacation rentals have a a pool or jacuzzi

Those traveling with a dog, cat or some other animal can stay in any of 9 accommodations that are designated as pet-friendly.

2,522 of our rentals in Wailea have been reviewed by previous guests. They rated 71% as great. You can instantly book any of 1,312 places to stay right now.

Destinations near Wailea

  • Kailua-Kona6,444 Properties
  • Princeville5,655 Properties
  • Kaanapali4,661 Properties
  • Honolulu3,891 Properties
  • Lahaina3,016 Properties
  • Kamuela2,717 Properties
  • Waikoloa2,608 Properties
  • Kihei2,509 Properties
  • Kapaa2,184 Properties
  • Kapalua1,649 Properties
  • Koloa1,597 Properties
  • Volcano1,253 Properties
  • Kahuku1,163 Properties
  • Maalaea1,127 Properties
  • Hilo1,101 Properties
  • Pahoa1,039 Properties
  • Wailua887 Properties
  • Captain Cook826 Properties
  • Lihue799 Properties
  • Keaau755 Properties
  • Hanalei517 Properties
  • Kailua (Oahu)513 Properties
  • Kapolei506 Properties
  • Maunaloa455 Properties
  • Haleiwa385 Properties
  • Hauula328 Properties
  • Kaunakakai303 Properties
  • Laie274 Properties
  • Waialua252 Properties
  • Waianae245 Properties
  • Waimanalo223 Properties
  • Ewa Beach221 Properties
  • Wailuku193 Properties
  • Paia189 Properties
  • Haiku136 Properties
  • Hawi117 Properties
  • Hana108 Properties
  • Mokuleia106 Properties
  • Hakalau106 Properties
  • Kaneohe102 Properties
  • Kekaha100 Properties
  • Kahului96 Properties
  • Kilauea82 Properties
  • Holualoa77 Properties
  • Honokaa71 Properties
  • Waipahu49 Properties
  • Waimea28 Properties
  • Mililani26 Properties