Ski Hotels - Vacation Rentals in Wailea Beach

Hale Hui Kai #112 in Kihei From US $420
         

10.0 (1 Review)
House
  • Pool
  • View
  • Wheelchair Accessible
Papaya Suite in Kihei From US $347
         

|
10.0 (10 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Hawaiian Cottage and Personal Paradise/BBKM 2013/0004 in Kihei From US $1,139
         

10.0 (208 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pool
Maui Vista 1207 in Kihei From US $197
         

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7.8 (16 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Luxurious Wailea Ocean Vistas in Kihei From US $1,151
         

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10.0 (8 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Keawakapu by Coldwell Banker Island Vacations in Wailea From US $518
         

New
House
  • Parking
  • Wheelchair Accessible
  • Child Friendly
NEW KITCHEN REMODEL! Amazing View! in Wailea From US $492
         

10.0 (159 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted in Kihei From US $695
         

Amazing view, Close to the beach, Wailea Ekahi Unit 20i in Wailea From US $541
         

10.0 (138 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Direct Oceanfront/Beachfront Luxury! Recently Remodeled in Kihei From US $814
         

10.0 (113 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Beachfront Condo B303 in Kihei From US $1,228
         

10.0 (101 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Maui Family Owned & Managed - Wailea Grand Champions Villa in Kihei From US $529
         

Wailea Ekahi 51F Oceanview - Walk to Beach in Kihei From US $405
         

9.8 (109 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Wailea Ekahi 14F - Best Views - 3 Minutes Walk to Beach in Wailea-Makena From US $836
         

10.0 (86 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Pro Tip: Skihotels makes it easy to compare the best listings on Skihotels homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Skihotels homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Wailea Beach.

Weather in Wailea Beach

View the weather forecast for Wailea Beach before booking your Wailea Beach Vacation Rentals to confirm your best time to go.

December - February
High 82°F       Low 63°F
March - May
High 86°F       Low 66°F
June - August
High 90°F       Low 71°F
September - November
High 90°F       Low 66°F

Wailea Beach Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Wailea Beach?

Currently, the total number of properties listed in 2026 is over 5443 in the Wailea Beach area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Wailea Beach.