Unplugged Weekend - Vacation Rentals in Wailea Beach

Ho'olei at Grand Wailea From US $2,198
         

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10.0 (4 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Signature Residences at Maui Banyan From US $849
         

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8.8 (11 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Aloha Kai-Ocean View Condo | 1 Bed, 1 Bath From US $273
         

9.6 (36 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Kihei Ali'i Kai Condos with Free Parking From US $528
         

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8.6 (24 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Ekolu 911 From US $452
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Wailea Beach Villas From US $1,169
         

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9.8 (187 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Spectacular 3rd Row Villa at Ho'olei with Ocean Views From US $1,420
         

10.0 (58 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Kihei Alii Kai A207 Renovated Kihei Condo Near Beach AC Pool From US $309
         

48 Hr Cancel, Partial Ocean View, A/C, 3 min Walk to Beach From US $487
         

10.0 (171 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Ocean And Mountain Views From US $263
         

10.0 (104 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Beautiful Condo in Kihei Alii Kai, steps from Kam 1 beach From US $297
         

DEC Sale Panoramic Ocean Views Fourth Row Ho'olei, 112-4 From US $1,533
         

10.0 (29 Reviews)
House
  • 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 355 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.