Wailea-Makena Vacation Rentals

Our Favorite Vacation Rentals in Wailea

  • The Villas at Fairmont Kea Lani
     5-star Villa
    Booking.com
    From
    $1,854
  • Wailea Ekolu 1602 - 2 Bedroom
     2br Home/Apartment
    HolidayLettings
    From
    $390
  • Kamaole Sands - Maui Condo & Home
     Home/Apartment
    NextTrip
    From
    $241
  • Mana Kai 611C
     Country House
    Booking.com
    From
    $384
  • Oceanview condo w/shared pool, tennis & beach across the street
     Home/Apartment
    HolidayLettings
    From
    $247
  • Residence Inn Maui Wailea
     Home/Apartment
    NextTrip
    From
    $830
  • Maui Vista 1102
    GoodCountry House
    Booking.com
    From
    $137
  • NEW LISTING! Airy condo w/shared pool/hot tub, steps to beach & Kihei activities
     2br Home/Apartment
    HolidayLettings
    From
    $371

Check prices for these upcoming dates

Wailea Vacation Rentals with a Pool

  • Gorgeous Ocean View Remodeled Wailea Condo (WE 38B)
    ExcellentHome/Apartment
    Airbnb
    From
    $508
  • Cottage by Wailea with Fabulous 180' Ocean view
    Excellent2br Home/Apartment
    Airbnb
    From
    $494
  • Perfect Tropical Beach Getaway
    GoodHome/Apartment
    Airbnb
    From
    $469
  • Worldmark Kihei Resort 2 BR 2 Bath Condo sleeps 6
    Excellent2br Home/Apartment
    Airbnb
    From
    $302

Wailea Vacation Rentals with Wi-Fi

  • The Heart of Kihei Studio
    ExcellentHome/Apartment
    Airbnb
    From
    $251
  • view
     2br Home/Apartment
    Airbnb
    From
    $291
  • Brand New 2018 Remodeled 2 King Beds/Sleeper Sofa!
    Excellent2br Home/Apartment
    Airbnb
    From
    $345
  • 180 Degree Ocean View in Wailea
    Excellent2br Home/Apartment
    Airbnb
    From
    $497

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
92° 69°
2
89° 65°
0
86° 64°
0
84° 62°
0
85° 62°
4
85° 60°
2
85° 67°
3
86° 66°
0
90° 69°
0
91° 70°
0
91° 70°
8
92° 68°
2
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Rainy days

This climate histogram shows you the weather patterns in Wailea. The warmest months in Wailea are March and April, when temperatures reach 92 ˚F. The coolest month is October, when temperatures drop to 60 ˚F. The wettest month in Wailea is May with 8.38 inches of rain, while the driest month is July with 0.03 inches of rain.

What Expert Travelers Think

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    Jeff CampbellMiddle Class Dad
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    Kacie MorganThe Rare Welsh Bit
  • — 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

    Jaz
    JazThe Life of a Social Butterfly

Vacation Rentals in Wailea

Browse places to stay from all your favorite providers including Airbnb, Bed and Breakfast, Agoda and more at AllTheRooms.com. Wailea has 3,873 hotels, vacation rentals and other special places to stay, with prices to suit budget travelers, extravagant travelers and everything in between. For those wanting to save money, the cheapest place to stay in Wailea comes in at $44 per night. In general, a place to stay in Wailea will cost you $346 per night.

If you would like to stay connected during your vacation, then you can choose from over 2,247 accommodations in Wailea that have WiFi. 18 places to stay include a morning meal. You can maintain your workout routine by staying at one of 433 accommodations that provide gym facilities. Driving to Wailea? Then choose one of the 2,187 places to stay that comes with a parking spot included. 609 places to stay have a a pool or jacuzzi

AllTheRooms has 16 pet-friendly places to stay in Wailea, so if you're traveling with your cat or dog you won't have any problems.

2,632 accommodations in Wailea have been reviewed; 71% are rated highly. 1,417 places to stay in are instantly bookable.

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