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Holiday Homes in Wailea

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    Travellers to Wailea are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 206 Rentals in Wailea
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    Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area1 / 28
    (38)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Beautifully renovated groundfloor Palms at Wailea 5031 / 24
    (50)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Modern Spacious Beachfront Luxury rental in Ekahi Village - Apartment 39F1 / 31
    (20)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Ocean View, Close to Beach&Pool Sleeps 10-$795 for all avail dates in April!!!1 / 24
    (59)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    96753, Wailea, Maui
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    'Best Vacation Ever' Say Our Guests! Luxurious & Affordable!1 / 43
    (38)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    96753, Wailea, Maui
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Luxurious Tropical Retreat  Wailea Ekahi Unit - 31 D1 / 24
    (70)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 2
    No Place Like Wailea - Ocean and Haleakala View - Renovated Top Floor1 / 24
    (68)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1 Bedroom, 2 Bathrooms, Sleeps 5 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 5
    Million Dollar Ocean & Golf Course Views from this beautiful 2 bed 2 bath Condo1 / 23
    (27)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Upscale Modern & Renovated with Designer Showers 1148 sq ft with 224 sq ft lanai1 / 44
    (68)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    96753, Wailea, Maui
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Luxury at its Best W/ Big Ocean Views!!1 / 23
    (33)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    5D - One of the closest to the Beach, Recently remodeled and very well equipped.1 / 24
    (50)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 5 Bedrooms, 2 Bathrooms, Sleeps 5
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    96753, Wailea, Maui
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    'Wailea Surf' Villa at Wailea Beach Villas: Exquisite Island Style Villa!1 / 23
    (72)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    96753, Wailea, Maui
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
    Enjoy Sweeping Ocean Views from this High End Remodel Top Floor Condo!1 / 36
    (63)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 3
    The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!1 / 50
    (69)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    96753, Wailea, Maui
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    5 Star Reviews! Wailea Ekolu with Ocean Views & Great Location!1 / 40
    (46)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    85+ 5* REVIEWS SAYS ALL! OCEAN/GOLF/REMOD/VAULTED/ FLR/last min specials!1 / 20
    (96)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • DVD Player
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    96753, Wailea, Maui
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
    WE OWN FIVE HOOLEI VILLAS ! WE SHOULD BE ABLE TO ACCOMODATE YOUR DATES!1 / 24
    (41)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    The Finest Ocean Views at the Palms at Wailea #12021 / 27
    (15)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Closest to Beach & Pool! We own five homes at Ho'olei!1 / 24
    (53)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    96753, Wailea, Maui
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Largest Two Bedroom/ Two Bath in the Village! Sleeps Eight. Close to the Beach.1 / 50
    (77)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Wailea, Oceanfront, Luxury, Polo Beach Club Condo #4031 / 24
    (37)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    96753, Wailea, Maui
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Panoramic Ocean View In The Heart Of Wailea On Golf Course1 / 24
    (39)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    96753, Wailea, Maui
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    1 Bedroom 2 Bath Top Floor corner unit Panoramic Ocean View Wailea Ekahi Village1 / 50
    (6)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 3
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Ocean Front, Luxury, Ground Floor, Remodeled, Polo Beach #1021 / 21
    (26)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Panoramic Ocean Views! - Wailea Beach Villas - Luxury 3 Bed / 3 Bath1 / 21
    (32)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Amazing 3 Bedrooms / 2 Bath condo with Ocean Views in Wailea, Maui!1 / 24
    (23)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Sept & Oct 2019 available in this Quiet, Spacious 1 Bdrm / 2 Bath1 / 24
    (27)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Charming Wailea Ekahi Condominium1 / 19
    (29)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Summer Special $199: Wailea Ekahi Beachfront Condo On Luxury Resort1 / 24
    (20)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
    Luxurious Sunlit One Bedroom Suite in Wailea 541 / 36
    (48)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    96753, Wailea, Maui
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Seaside Tropics Villa - Pool, AC, Large grounds w/ Fruit trees1 / 28
    (10)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    96753, Wailea, Maui
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Ocean View Luxury -- Sleep to the Sound of the Waves1 / 16
    (15)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Ekahi 6B - Amazing Location! One Minute to Beach & Pool!1 / 23
    (22)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 3 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 3
    Superior ocean end 1bd/1ba Ocean full Condo with1 / 26
    (8)Excellent
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    96753, Wailea, Maui
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    96753, Wailea, Maui
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Golden Mandarin Pool Villa D102 with Private Plunge Pool1 / 50
    (6)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Immaculate, Luxury Comfort, Stunning Views - Hawaiian-Chic, Mid-Century Modern1 / 38
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
    PRIVATE PLUNGE POOL! Bali Hai Pool Villa F102 at Wailea Beach Villas1 / 50
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    96753, Wailea, Maui
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    The Peaceful Palms at Wailea.......Welcomes You!1 / 24
    (28)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    So close to the ocean you can hear the waves!  Quiet and private! Flat walk!1 / 24
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    96753, Wailea, Maui
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    1
    Wailea Holiday Rentals

    If you're flying halfway around the world to visit Hawaii then you'll want to have a comfortable stay once you get there, and there are a huge number of holiday rental properties where you can make yourself at home completely and relax and enjoy your holiday in the volcanic island paradise. Wailea is in the south of Maui, Hawaii's second biggest island, and you will need at least a week to sample all the activities that the region has to offer. Hawaii is probably not the first place you would think of for a family friendly holiday, but with beachfront condos and villas available for less than $1,000 a week, and dozens of amazing beaches all around, Wailea is great for kids and can certainly work out as a money saving option compared to the highly expensive hotels of Wailea resort.

    Things to do in Wailea

    Obviously you will be wanting to hit the beach in Hawaii, and there are many from which you can choose, such as Keawakapu Beach, surrounded by golf courses. If you don't want to spend all your time lying on one of the many south-facing beaches but aren't quite brave enough to go and climb a volcano, Wailea has many things to do for all ages, from playing golf and tennis to the inevitable shops and restaurants, all in an incredible Pacific climate. Wailea is fairly sparsely populated, with around 6,000 inhabitants, so you can also have a great time exploring the countryside nearby.

    Renting villas and condos in Wailea

    Wailea Resort is a wonderful place to visit and stay, but its planning is a bit contrived - the Wailea Community Association issue guidelines for new buildings aiming to preserve the island feel of Maui. With the additional aim of low population density, this does mean that prices even for holiday rentals may be higher than in other parts of the Hawaii island chain. But with the scary prices charged by hotels, and the extra flexibility associated with renting your own villa or condo for your family, Wailea holiday rentals still represent fantastic value for money. With air conditioning thankfully coming as virtually standard, and difficult choices of whether you'd prefer views of a volcano, a golf course, or perhaps a beach, it's an idyllic place to enjoy a great family holiday. And if you are looking for a low cost Pacific break, nothing beats buying local produce and cooking it up in your very own kitchen for the week, rather than relying on a hotel's expensive restaurants.

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