Wailea-Makena Vacation Rentals

Our Favorite Vacation Rentals in Wailea

  • 4-309 Kamaole Sands**Newly Remodeled** Steps to Kamaole 3 Beach!
     Country House
    Booking.com
    From
    $474
  • LUXURY BEACH HOME POOL EXCELLENT LOCATION
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $3,820
  • Kauhale Makai 203 Condo
     Home/Apartment
    Booking.com
    From
    $424
  • Royal Mauian 503 - 2 Bedroom
     2br Home/Apartment
    HolidayLettings
    From
    $618
  • Kauhale Makai 235
     Country House
    Booking.com
    From
    $213
  • 80 Series Land Cruiser Roof Top Tent RTT rental in Maui
     Home/Apartment
    HolidayLettings
    From
    $199
  • MAALAEA SURF, #F-2
    ExcellentHome/Apartment
    HolidayLettings
    From
    $327
  • Homey Comfort+Style! Upgraded Kitchen, WiFi, Roomy Lanai–Kamaole Sands 7208
     Home/Apartment
    HolidayLettings
    From
    $1,358

Check prices for these upcoming dates

Wailea Vacation Rentals with a Pool

  • Honalua || Wailea Ekahi Unit 2D || Lowered Rates
    Excellent2br Home/Apartment
    Airbnb
    From
    $815
  • 🌟Maui Tropical Getaway🌟 Walk Across to the Beach🏖
    ExcellentHome/Apartment
    Airbnb
    From
    $647
  • 🍍Perfect Tropical Beach Getaway🌴
    GoodHome/Apartment
    Airbnb
    From
    $997
  • Beautiful & freshly updated 1BD. Walk to beaches
    GoodHome/Apartment
    Airbnb
    From
    $873

Wailea Vacation Rentals with Wi-Fi

  • Island Sands 104 Fantastic ground floor with Ocean Views!
    ExcellentHome/Apartment
    Airbnb
    From
    $339
  • Ocean View Superior Deluxe - #200
    ExcellentHome/Apartment
    Airbnb
    From
    $354
  • ★ Walk to the Beach. Relaxing Resort Retreat ★
    GoodHome/Apartment
    Airbnb
    From
    $757
  • 4-309 Kamaole Sands**Newly Remodeled** Steps to Kamaole 3 Beach!
    ExcellentHome/Apartment
    Airbnb
    From
    $550

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
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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
85° 62°
1
84° 58°
2
86° 60°
0
88° 65°
0
91° 62°
1
92° 68°
1
91° 70°
0
90° 72°
1
91° 72°
0
91° 71°
0
88° 69°
0
86° 69°
2
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Wailea. The warmest months in Wailea are July and March, when temperatures reach 92 ˚F. The coolest month is November, when temperatures drop to 58 ˚F. The wettest month in Wailea is November with 2.39 inches of rain, while the driest month is December with 0.72 inches of rain.

What Expert Travelers Think

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    Max HobbsLTL Mandarin School
  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

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    JazThe Life of a Social Butterfly
  • — 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
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Vacation Rentals in Wailea

Browse rentals from all your favorite providers including Airbnb, Priceline, Agoda and more at AllTheRooms.com. Wailea has 3,480 hotels, vacation rentals and other special places to stay, with prices to suit careful travellers, luxury travelers and everything in between. If you are wanting to keep costs down, the cheapest place to stay in Wailea is only $50 a night. On average, a place to stay in Wailea will cost you $332 per night.

If you want to stay connected during your trip, then you can choose from over 632 accommodations in Wailea that have WiFi. We have 16 accommodations that come with breakfast included. Choose from 130 accommodations that provide gym facilities, so you don't miss a single workout. Driving to Wailea? Then choose one of the 620 places to stay that comes with a parking spot included. We have 573 vacation rentals that have a pool or jacuzzi.

If you're traveling with your best friend, then be sure to choose one of the 8 pet-friendly accommodations available.

2,498 of our accommodations in Wailea have been reviewed and rated. 70% are rated great. 1,237 places to stay in are instantly bookable.

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