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Wailea: Vacation Rental By Owner

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  • Property-1 Image 1
    Villa Select Dates for Price
    • 3Bed
    • 3Baths
    • (3) Excellent
    Wailea, HI

    State of Hawaii Transient Accommodations Tax License #TA-098-627-9936-01 Orient Pacific Suite J505 is located on Maui island ranked #1 Best Luxury Destination in... ...more

  • Property-2 Image 1
    Villa Select Dates for Price
    • 3Bed
    • 4Baths
    • (7) Exceptional
    Wailea, HI

    State of Hawaii Transient Accommodations Tax License #TA-116-313-0880-02 Golden Mandarin Pool Villa D102 is located on Maui island ranked #1 Best Luxury... ...more

  • Property-3 Image 1
    Villa Select Dates for Price
    • 3Bed
    • 4Baths
    Wailea, HI

    State of Hawaii Transient Accommodations Tax License #TA-102-149-9392-02 County of Maui Short-Term Rental License #Hotel-Zoned Resort Amore Aloha Villa 813 is... ...more

  • Property-4 Image 1
    Villa Select Dates for Price
    • 4Bed
    • 3Baths
    • (2) Exceptional
    Wailea, HI

    State of Hawaii Transient Accommodations Tax License #TA-094-662-2464-03 Sandcastles Suite L509 is located on Maui island ranked #1 Best Luxury Destination in... ...more

  • Property-5 Image 1
    Villa Select Dates for Price
    • 3Bed
    • 4Baths
    • (3) Exceptional
    Wailea, HI

    State of Hawaii Transient Accommodations Tax License #TA-094-662-2464-01 Royal Ilima A201 is located on Maui island ranked #1 Best Luxury Destination in the USA... ...more

  • Property-6 Image 1
    Villa Select Dates for Price
    • 3Bed
    • 4Baths
    • (7) Exceptional
    Wailea, HI

    State of Hawaii Transient Accommodations Tax License #TA-071-739-0848-01 Castaway Cove C201 is located on Maui island ranked #1 Best Luxury Destination in the... ...more

  • Property-7 Image 1
    Condo $421 / Nightly
    • 2Bed
    • 2Baths
    • (15)
    Wailea, HI

    Welcome to the absolute finest ocean views to be found at The Palms at Wailea. This spacious top floor unit, features an expansive living room, with loft and... ...more

  • Property-8 Image 1
    Condo $480 / Nightly
    • 1Bed
    • 1Baths
    • (67)
    Wailea, HI

    Encase yourself in luxurious comfort while you soak up the amazing sights, sounds and warm sunshine of beautiful Wailea, Maui. From the moment you walk in to... ...more

  • Property-9 Image 1
    Condo Select Dates for Price
    • 2Bed
    • 2Baths
    Wailea, HI

    Property Location With a stay at this condo in Kihei (Wailea), you'll be a 4-minute drive from Keawakapu Beach and 6 minutes from Wailea Beach. This condo is... ...more

  • Property-10 Image 1
    Condo Select Dates for Price
    • 1Bed
    • 2Baths
    Wailea, HI

    Property Location With a stay at this condo in Kihei (Wailea), you'll be a 4-minute drive from Keawakapu Beach and 6 minutes from Wailea Beach. This condo is... ...more

  • Property-11 Image 1
    Condo Select Dates for Price
    • 2Bed
    • 2Baths
    Wailea, HI

    Property Location With a stay at this condo in Kihei (Wailea), you'll be a 5-minute drive from Keawakapu Beach and 7 minutes from Wailea Beach. This condo is... ...more

  • Property-12 Image 1
    Condo Select Dates for Price
    • 3Bed
    • 2Baths
    Wailea, HI

    Property Location With a stay at this condo in Kihei (Wailea), you'll be a 5-minute drive from Keawakapu Beach and 7 minutes from Wailea Beach. This condo is... ...more

  • Property-13 Image 1
    Condo Select Dates for Price
    • 1Bed
    • 2Baths
    Wailea, HI

    Property Location With a stay at this condo in Kihei (Wailea), you'll be a 5-minute drive from Keawakapu Beach and 7 minutes from Wailea Beach. This condo is... ...more

  • Property-14 Image 1
    Condo Select Dates for Price
    • 2Bed
    • 2Baths
    Wailea, HI

    Property Location With a stay at this condo in Kihei (Wailea), you'll be a 4-minute drive from Keawakapu Beach and 6 minutes from Wailea Beach. This 4-star... ...more

  • Property-15 Image 1
    Villa Select Dates for Price
    • 3Bed
    • 4Baths
    • (5) Wonderful
    Wailea, HI

    State of Hawaii Transient Accommodations Tax License #TA-154-353-8688-01 Sun Splash C301 is located on Maui island ranked #1 Best Luxury Destination in the USA... ...more

  • Property-16 Image 1
    Villa Select Dates for Price
    • 3Bed
    • 3Baths
    • (6) Exceptional
    Wailea, HI

    State of Hawaii Transient Accommodations Tax License #TA-120-405-4016-01 Sandy Surf K508 is located on Maui island ranked #1 Best Luxury Destination in the USA... ...more

  • Property-17 Image 1
    Villa Select Dates for Price
    • 3Bed
    • 2Baths
    • (13)
    Wailea, HI

    State of Hawaii Transient Accommodations Tax License #TA-195-772-6208-01 Regal Mandalay M511 is located on Maui island ranked #1 Best Luxury Destination in the... ...more

  • Property-18 Image 1
    Villa Select Dates for Price
    • 3Bed
    • 2Baths
    • (7) Excellent
    Wailea, HI

    State of Hawaii Transient Accommodations Tax License #TA-094-662-2464-04 Wailea Seashore Suite K507 is located on Maui island ranked #1 Best Luxury Destination... ...more

  • Property-19 Image 1
    Condo Select Dates for Price
    • 2Bed
    • 2Baths
    Wailea, HI

    Property Location With a stay at this condo in Kihei (Wailea), you'll be a 4-minute drive from Keawakapu Beach and 6 minutes from Wailea Beach. This condo is... ...more

  • Property-20 Image 1
    Condo $313 / Nightly
    • 2Bed
    • 2Baths
    • (71)
    Wailea, HI

    WELCOME TO OUR HAWAIIAN RETREAT! - RENOVATED in September 2015! Many upgrades including a completely new kitchen, new bathrooms, new tile flooring, new furniture... ...more

Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Wailea. Many accommodations in Wailea provide "Beach", there are 4, or there are 4 of Vacation Rentals in Wailea with a "Romantic", there are also 4 with "Scuba Diving - Snorkling", which is another great reason to visit Wailea.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Wailea. The most expensive month of the next 12 months is in January, where prices hit an average of $108 a night. In , prices will hit an average low of $0 per night.