Unplugged Weekend - Vacation Rentals in Wailea Beach

Ho'olei at Grand Wailea From US $1,808
         

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10.0 (5 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Kihei Ali'i Kai Condos with Free Parking From US $559
         

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9.6 (50 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Pacific Shores B118 by Coldwell Banker Island Vacations From US $231
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Signature Residences at Maui Banyan From US $513
         

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8.8 (33 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Wailea Beach Villa H202 by Coldwell Banker Island Vacations From US $1,372
         

Spectacular 3rd Row Villa at Ho'olei with Ocean Views From US $1,397
         

10.0 (63 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Renovated Kihei Condo Near Beach AC Pool - Kihei Alii Kai A207 From US $430
         

Beautiful Condo in Kihei Alii Kai, steps from Kam 1 beach From US $280
         

Summer Sale Panoramic Ocean Views Fourth Row Ho'olei, 112-4 From US $1,551
         

Beachside Kihei retreat w/pool & hot tub From US $687
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Kihei Alii Kai Ocean Retreat Top Floor C407 From US $531
         

10.0 (3 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Pro Tip: Unpluggedweekend makes it easy to compare the best listings on Unpluggedweekend homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Unpluggedweekend 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

What are the top vacation rentals in Wailea Beach?
How many vacation rentals are available in Wailea Beach?

Currently, the total number of properties listed in 2026 is over 399 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.