Wailea: Vacation Rental By Owner

Showing 20 Of 105 Vacation Rentals
  • Property-1 Image 1
    Condo Select Dates for Price
    • 1 Bed
    • 2 Baths
    • (13) Exceptional
    Wailea, HI

    Highly cleaned and sanitized for your vacation. Ask about out AlohaSafeStay program. NEW! For the First time in rental pool - Gorgeous and spacious ground... ...more

  • Property-2 Image 1
    Condo $749 / Nightly
    • 2 Bed
    • 2 Baths
    • (14)
    Wailea, HI

    Wailea Elua Village is the premier resort community located directly on Ulua beach in Wailea featuring 24 acres of lush tropical landscapes, luxury accommodations... ...more

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

    Wailea Elua Village is a premier property located on the beach in Wailea featuring 152 condos on 24 acres of lush tropical landscapes. Luxury accommodations and... ...more

  • Property-4 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 2 Baths
    Wailea, HI

    The world is changing, and we are changing with it. Here at CB Island Vacations, we have taken the time to revamp our practices to ensure a clean and safe... ...more

  • Property-5 Image 1
    Villa Select Dates for Price
    • 3 Bed
    • 4 Baths
    • (17)
    Wailea, HI

    The world is changing, and we are changing with it. Here at CB Island Vacations, we have taken the time to revamp our practices to ensure a clean and safe... ...more

  • Property-6 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (15)
    Wailea, HI

    The world is changing, and we are changing with it. Here at CB Island Vacations, we have taken the time to revamp our practices to ensure a clean and safe... ...more

  • Property-7 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (22)
    Wailea, HI

    A modern 2 bedroom, 2 bath condo w. extra bunk beds and an amazing ocean view! South Maui is one of the most beautiful destinations in all of Maui and Wailea... ...more

  • Property-8 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (37) Excellent
    Wailea, HI

    Palms at Wailea #205 is a fully remodeled, 2 bedroom / 2 bath unit with a tropical garden view, with a partial ocean view from the lanai and living room. Located... ...more

  • Property-9 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (53)
    Wailea, HI

    Palms at Wailea #1503 is one of the best located condos in this property; situated in the inner circle providing views out to Maalaea Bay, West Maui Mountains... ...more

  • Property-10 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (50)
    Wailea, HI

    Palms at Wailea #603 has a fully equipped kitchen, washer and dryer and unlike most units at the Palms, it is fully air conditioned. It has flat screen TVs, high... ...more

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

    Palms at Wailea #1508 is an upstairs ocean view 2 bedroom 2 bath unit with a full kitchen, washer and dryer, fully air conditioned, high speed wireless service.... ...more

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

    Palms at Wailea #308 is a 1 bedroom, 2 bath unit on the second floor with split system A/C throughout, a fully equipped kitchen, washer and dryer, 2 flat-screen... ...more

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

    Palms at Wailea #704 is a 2 bedroom, 2 bath unit on the second floor with a partial ocean view, and split system A/C in both bedrooms and the living. There is a... ...more

  • Property-14 Image 1
    Condo Select Dates for Price
    • 1 Bed
    • 1 Baths
    • (21) Excellent
    Wailea, HI

    Wailea Ekahi #25-C is a 1 bedroom, 1 bath ground floor condo with room unit air conditioning in both the living room and bedroom, a fully-equipped kitchen, washer... ...more

  • Property-15 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 1 Baths
    • (47)
    Wailea, HI

    Leinaala #105 is a 2 bedroom, 1 bath ground floor ocean front unit with an amazing panoramic ocean view. It has a fully-equipped kitchen, a flat-screen TV, DVD... ...more

  • Property-16 Image 1
    Condo Select Dates for Price
    • 1 Bed
    • 1 Baths
    • (12) Wonderful
    Wailea, HI

    The world is changing, and we are changing with it. Here at CB Island Vacations, we have taken the time to revamp our practices to ensure a clean and safe... ...more

  • Property-17 Image 1
    Villa Select Dates for Price
    • 3 Bed
    • 4 Baths
    • (15)
    Wailea, HI

    The world is changing, and we are changing with it. Here at CB Island Vacations, we have taken the time to revamp our practices to ensure a clean and safe... ...more

  • Property-18 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (18)
    Wailea, HI

    The world is changing, and we are changing with it. Here at CB Island Vacations, we have taken the time to revamp our practices to ensure a clean and safe... ...more

  • Property-19 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (104)
    Wailea, HI

    Wailea Grand Champions #48 2 bd, 2 ba ocean view unit. This beautiful 2 bedroom, 2 bath vaulted-ceiling penthouse unit includes 180° expansive ocean views and... ...more

  • Property-20 Image 1
    Condo Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (51) Excellent
    Wailea, HI

    Wailea Grand Champions #45 is a tastefully remodeled 2 bedroom 2 bath unit on the 3rd floor with an incredible ocean view. Please note that there is no elevator... ...more

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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 July, where prices hit an average of $22 a night. In June, prices will hit an average low of $80 per night.