Hoolei Vacation Rentals

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  • Beautifully furnished Ho'olei Villa w/ Largest Floor Plan! Hoolei 24-1

    This property is hotel zoned, and not being affected by the recent proposed legislation.

    Wailea beach, voted one of the top beaches in the World, is a short walk from Ho’olei Villas. This amazing beach has numerous activities such as ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kihei
    52  reviews
    from $1,427 
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  • I.P.M PRESENTS: HOOLEI 69-2: GREAT LOCATION + VIEW. FLEXIBLE CANCELATION POLICY

    SECURE YOUR RESERVATION WITHIN MINUTES!
    SAFE AND SECURE ON LINE BOOKING AND PAYMENT PROCESS!
    24 HOUR PROFESSIONAL PROPERTY MANAGEMENT SERVICES!
    HAWAII TAT #: W23624545-01

    HO'OLEI VILLA: 69-2

    CANCELLATION POLICY ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kihei
    32  reviews
    from $1,346 
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  • I.P.M PRESENTS: HOOLEI 81-4: NEW REMODEL AND DECOR + FLEXIBLE CANCELATION POLICY

    SECURE YOUR RESERVATION WITHIN MINUTES!
    SAFE AND SECURE ON LINE BOOKING AND PAYMENT PROCESS!
    24 HOUR PROFESSIONAL PROPERTY MANAGEMENT SERVICES!
    HAWAII TAT #: W23624545-01

    HO'OLEI VILLA: 81-4

    CANCELLATION POLICY ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 6
    Hawaii> Kihei
    40  reviews
    from $1,095 
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  • Hoolei Uni 31-2 Ocean view- ideal Wailea location walking to beaches and shops

    Dramatic ocean views, this spacious town home is approximately 2500 sq ft of interior footage and 596 sq ft of lanai space. The Hoolei community is located directly across the street from the Four Seasons and the Grand Wailea Resort. Unit 31-2 ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Wailea-Makena
    63  reviews
    from $1,534 
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  • Luxurious Ocean View Villa at Ho'olei! Experience Hoolei 17-3

    This property is hotel zoned, and not being affected by the recent proposed legislation.

    Located in highly desirable secluded area of neighborhood your villa welcomes you with spacious floor plan and sweeping ocean views. Marvel at the ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Wailea
    58  reviews
    from $1,747 
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  • I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY

    SECURE YOUR RESERVATION WITHIN MINUTES!
    SAFE AND SECURE ON LINE BOOKING AND PAYMENT PROCESS!
    24 HOUR PROFESSIONAL PROPERTY MANAGEMENT SERVICES!

    HO'OLEI VILLA 93-1 is a brand new addition to the IPM Portfolio of fine luxury ...

    • 4 bedroom
    • 4 bathroom
    • Sleeps 10
    Hawaii> Kihei
    21  reviews
    from $1,401 
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  • Hawaii Life Vacations Hoolei Wailea Lux Residence Overlooking Resort Pool

    Hawaii Life Vacations reminds you that Life is Grand at Ho'olei , an exclusive gated community located directly across the street and a short walking distance to the renowned Wailea Beach and the Grand Wailea Resort. Residence #93-3 is one of ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Wailea
    23  reviews
    from $1,170 
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  • Hoolei 23-3 Deluxe Ocean View Wailea Residence Personifies Maui Lux Living

    Hawaii Life Vacations presents residence #23-3 (L3) at Ho’olei in the heart of the Wailea Resort in South Maui. Located on the third row of this deluxe townhome vacation rental community, the views are Vast and unobstructed, yet still feel ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 6
    Hawaii> Wailea
    1  reviews
    from $1,237 
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  • I.P.M PRESENTS: HOOLEI 99-2 BRAND NEW REMODEL - WOW! FLEXIBLE CANCELATION POLICY

    SECURE YOUR RESERVATION WITHIN MINUTES!
    SAFE AND SECURE ON LINE BOOKING AND PAYMENT PROCESS!
    24 HOUR PROFESSIONAL PROPERTY MANAGEMENT SERVICES!
    HAWAII TAT#: W67761941-01

    HO'OLEI VILLA: 99-2

    CANCELLATION POLICY ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kihei
    10  reviews
    from $1,143 
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  • I.P.M PRESENTS: HOOLEI 81-3. NEW REMODEL + VIEW. FLEXIBLE CANCELATION POLICY

    SECURE YOUR RESERVATION WITHIN MINUTES!
    SAFE AND SECURE ON LINE BOOKING AND PAYMENT PROCESS!
    24 HOUR PROFESSIONAL PROPERTY MANAGEMENT SERVICES!
    HAWAII TAT #: W23624545-01

    HO'OLEI VILLA: 81-3

    CANCELLATION POLICY ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 6
    Hawaii> Kihei
    27  reviews
    from $1,346 
      View Property
  • I.P.M PRESENTS: HOOLEI 21-6. STUNNING DECOR + VIEW + FLEXIBLE CANCELATION POLICY

    SECURE YOUR RESERVATION WITHIN MINUTES!
    SAFE AND SECURE ON LINE BOOKING AND PAYMENT PROCESS!
    24 HOUR PROFESSIONAL PROPERTY MANAGEMENT SERVICES!
    HAWAII TAT#: TA-061-535-6416-01

    HO'OLEI VILLA: 21-6

    CANCELLATION POLICY ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kihei
    30  reviews
    from $1,086 
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