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House Rentals in Wailea, HI

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    Travelers to Wailea are booking December dates now. Secure your vacation rental today, and have the perfect trip.
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    $2,093
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    1 / 35
    5 of 5 stars (2) Excellent
    1 Bedroom / 2 Bathrooms / Sleeps 5
    travelers have booked this property
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    $2,998
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    1 / 14
    4.5 of 5 stars (6) Very good
    1 Bedroom / 2 Bathrooms / Sleeps 3
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    $1,350
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    1 / 23
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    $395
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    1 / 29
    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    Amenities & Details
    • Satellite TV
    • Water Views
    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • DVD Player
    • Private Outdoor...
    • Watersports Nearby
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
    About this property
    Note: *** Our calendar is always up to date. Low Season Rate (Apr 16 - Dec 15) $395.00 per night High Season Rate (Dec 16 - Apr 15) $450.00 per night Are you looking for a quiet peaceful alternative vacation experience away from the hotel zone but minutes away from South Maui's best beaches,... View all property information
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    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed July 27, 2014
    We were traveling with our three kids and we really liked the house. Very comfortable with enough space for every one. By looking at the pictures we knew what to expect and were...
    5 of 5 stars Reviewed July 8, 2014
    The wife and I and are 3 children (9, 9 and 3) stayed here for 8 nights! Looked at many homes in Maui and man did I nail it with this one! Perfect location, perfect owners...
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    From
    $870
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    1 / 24
    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    Amenities & Details
    • Washer
    • DVD Player
    • Hot Tub
    • Gym
    • Air Conditioning
    • Private Outdoor...
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Description TAKE ADVANTAGE OF THE BEST DEAL IN HOOLEI. Check availability and BOOK before its gone! Hoolei Haven is a newly built state-of-the-art luxury townhome with beautiful three bedrooms, three and one-half baths, 3363 square foot villa with large lanais located across from the Grand Wailea... View all property information
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    Wailea, Maui 96753
    From
    $1,295
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    1 / 89
    4.5 of 5 stars (4) Very good
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    • Internet Access
    • Water Views
    • Stereo System
    • Hot Tub
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    In November 2014, Wailea Beach Villas was awarded three accolades by Conde Nast Traveler’s Readers Choice Awards. Newest designations for Wailea Beach Villas: No. 1 Resort in Hawaii with a rating of 94.242, No. 11 in the Top 25 Resorts in the U.S., and #51 of the Top 100 Hotels &... View all property information
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    Wailea, Maui 96753
    From
    $495
    / Night
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    1 / 34
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Private Outdoor...
    • Water Views
    • Hot Tub
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Come stay with us here in sunny south Maui at our beautiful, lovingly remodeled ocean view home with private pool. There are amazing ocean views from almost all rooms in the house and the wrap around covered deck is perfect for indoor/outdoor style island living. Several beautiful white sand... View all property information
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    Wailea, Maui 96753
    From
    $1,095
    / Night
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    1 / 83
    5 of 5 stars (1) Excellent
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Internet Access
    • Stereo System
    • Satellite TV
    • Shared Outdoor Pool...
    • Water Views
    • Hot Tub
    • Air Conditioning
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    In November 2014, Wailea Beach Villas was awarded three accolades by Conde Nast Traveler’s Readers Choice Awards. Newest designations for Wailea Beach Villas: No. 1 Resort in Hawaii with a rating of 94.242, No. 11 in the Top 25 Resorts in the U.S., and #51 of the Top 100 Hotels &... View all property information
    Make Inquiry
    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed August 14, 2014
    We rented Castaway Cove, Unit C201 at the Wailea Beach Villas on Maui in July 2014. This unit is managed by Tropical Villas Vacations. Our first visit to Maui and "wow" what a...
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    From
    $1,850
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    1 / 78
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Stereo System
    • Grill
    • Refrigerator
    • Internet Access
    • Dishwasher
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    In November 2014, Wailea Beach Villas was awarded three accolades by Conde Nast Traveler’s Readers Choice Awards. Newest designations for Wailea Beach Villas: No. 1 Resort in Hawaii with a rating of 94.242, No. 11 in the Top 25 Resorts in the U.S., and #51 of the Top 100 Hotels &... View all property information
    Make Inquiry
    Location Information
    Wailea, Maui 96753
    From
    $1,195
    / Night
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    1 / 85
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Parking
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    an glass cooking range, juicer, two coffee makers with timers, integrated sub-zero wine/refrigerator with dual-climate wine storage and two sub-zero refrigerator/freezers with ice maker, various condiments and cooking supplies including sugar packets, answering machine, wool berber carpets, full... View all property information
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    Location Information
    Wailea, Maui 96753
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    From
    $1,595
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    1 / 82
    4 of 5 stars (2) Very good
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Grill
    • Dishwasher
    • Air Conditioning
    • Stereo System
    • Internet Access
    • Hot Tub
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    In November 2014, Wailea Beach Villas was awarded three accolades by Conde Nast Traveler’s Readers Choice Awards. Newest designations for Wailea Beach Villas: No. 1 Resort in Hawaii with a rating of 94.242, No. 11 in the Top 25 Resorts in the U.S., and #51 of the Top 100 Hotels &... View all property information
    Make Inquiry
    Location Information
    Wailea, Maui 96753
    From
    $1,595
    / Night
    View Details
    1 / 87
    5 of 5 stars (5) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 9
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Grill
    • Dishwasher
    • Hot Tub
    • Stereo System
    • Refrigerator
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    with bona-fide HD cable boxes and HD service subscriptions, DVD/CD players, DVR’s for recording programs while at the beach, and most villas have NETFLIX accounts for unlimited TV show and movie viewing! Some villas have gaming devices, and others are now adding Apple TV... View all property information
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    Location Information
    Wailea, Maui 96753
    From
    $1,295
    / Night
    View Details
    1 / 71
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Hot Tub
    • Dishwasher
    • Stereo System
    • Grill
    • Internet Access
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    In November 2014, Wailea Beach Villas was awarded three accolades by Conde Nast Traveler’s Readers Choice Awards. Newest designations for Wailea Beach Villas: No. 1 Resort in Hawaii with a rating of 94.242, No. 11 in the Top 25 Resorts in the U.S., and #51 of the Top 100 Hotels &... View all property information
    Make Inquiry
    Location Information
    Wailea, Maui 96753
    From
    $995
    / Night
    View Details
    1 / 83
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Grill
    • Air Conditioning
    • Dishwasher
    • Hot Tub
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    change until you secure your villa of choice with a partial deposit payment and a completed rental agreement. Additional amenities include: marble floors, and umbrellas. gourmet kitchen with an extensive range of equipment and supplies including an espresso-maker, good quality cutting knives,... View all property information
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    Location Information
    Wailea, Maui 96753
    From
    $249
    / Night
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    1 / 20
    5 of 5 stars (38) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (38) Make Inquiry
    Amenities & Details
    • Microwave
    • Dishwasher
    • Internet Access
    • Grill
    • Hot Tub
    • Air Conditioning
    • Stereo System
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Visit www.rainbowdeluxe.com for more info! Rainbow Deluxe is a standout 2 bedroom / 2 bath vacation home conveniently located in Maui Meadows, along the south shore of Maui, Hawaii. This 700 square foot luxury Polynesian pole cottage sits on its own quarter acre, private driveway entrance, ideally... View all property information
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    Location Information
    Wailea, Maui 96753
    5 of 5 stars Reviewed June 12, 2015
    We just returned from a two week stay at this lovely cottage. The owners think of every detail from the welcoming treats to everything you could need to make your stay more...
    5 of 5 stars Reviewed May 23, 2015
    My wife and I spent the first week of our honeymoon in Rainbow Deluxe and could not have been happier! It was perfect! When we arrived there was a cornucopia of fruit, snacks and...
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