Wailea-Makena Vacation Rentals

Our Favorite Vacation Rentals in Wailea

  • Grand Champions 78, 2 Bedrooms, Golf View, WiFi, Pool Access, Sleeps 4
     Country House
    Booking.com
    From
    $525
  • 2960 S Kihei Rd Condo Unit 207
     Home/Apartment
    Booking.com
    From
    $809
  • Maui Kamaole G201
     Country House
    Booking.com
    From
    $409
  • Maui Banyan T-305 - Ocean View Beach Condo for 10
     Country House
    Booking.com
    From
    $649
  • Maui Sunset B402 Condo
     Home/Apartment
    Booking.com
    From
    $249
  • 246 Hale Kamaole
     Country House
    Booking.com
    From
    $476
  • Maui Banyan P-302 - 2 Bedrooms, 3rd Floor, Near Beach, 2 Pools, Hot Tubs
     Country House
    Booking.com
    From
    $450
  • Maui Banyan G-101 - 2 Bedrooms, Ground-floor, Renovations, close to beach, Pools, Hot Tubs
     Country House
    Booking.com
    From
    $484

Check prices for these upcoming dates

Wailea Vacation Rentals with a Pool

  • Family friend 2Bd/2BA Palms Wailea FullAC TAX incl
    Excellent2br Home/Apartment
    Airbnb
    From
    $570
  • 2BR Pacific Shores by the Beach
    Excellent2br Home/Apartment
    Airbnb
    From
    $342
  • Beachfront Full OceanMtn Views-Walk to everything!
    ExcellentHome/Apartment
    Airbnb
    From
    $650
  • 🍍Perfect Tropical Beach Getaway🌴
    GoodHome/Apartment
    Airbnb
    From
    $799

Wailea Vacation Rentals with Wi-Fi

  • Palm Cottage
    Excellent2br Home/Apartment
    Airbnb
    From
    $436
  • South Maui Oceanview solo cottage
    ExcellentCountry House
    Airbnb
    From
    $359
  • #2 TRACY’S TROPICAL TREASURES:VOTED #1 IN MAUI!
    ExcellentHome/Apartment
    Airbnb
    From
    $420
  • Oceanfront Penthouse, Stunning 1bd
    GoodHome/Apartment
    Airbnb
    From
    $441

Wailea Pet-Friendly Vacation Rentals

  • GROUND FLOOR PARADISE OASIS NEXT TO THE BEACH.
    ExcellentHome/Apartment
    Airbnb
    From
    $341

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
86° 64°
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86° 66°
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90° 69°
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91° 70°
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91° 70°
8
92° 68°
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92° 69°
2
89° 65°
0
Dec
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Rainy days

This climate histogram shows you the weather patterns in Wailea. The hottest month in Wailea is March, when temperatures peak at 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

  • — 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
  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE
  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad

Vacation Rentals in Wailea

Find the perfect rental for your vacation at AllTheRooms.com. We aggregate Airbnb, Priceline, Bed and Breakfast and others. Wailea has 3,957 hotels, vacation rentals and other unique places to stay, with prices to suit careful travellers, luxury travelers and everything in between. If you are trying to save money, the cheapest place to stay in Wailea is just $50 per night. An average rental in Wailea costs on average $346 per night.

If you want internet access during your stay in Wailea, then you can choose from over 692 places to stay that provide WiFi internet. 18 places to stay include a breakfast. Choose from 131 accommodations that provide gym options, so you don't miss a single workout. If you are driving to Wailea, you'll want to pick from 680 places to stay that provide parking. We have 612 hotels and vacation rentals that have a pool or jacuzzi.

If you're traveling with your best friend, then make sure to select one of the 9 pet-friendly accommodations available.

2,615 of our accommodations in Wailea have been reviewed and rated. 69% are rated excellent or good. 1,495 accommodations allow instant booking.

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