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Wailea Vacation Rentals

Hotels (7)

B&Bs / Inns (0)

Specialty Lodging (8)

Vacation Rentals (63)

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Contact Owner
Nightly rate from
$895
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 3
Luxury awaits in this exquisite three bedroom, three full baths, 2500 square feet Penthouse Villa J205 with gorgeous ocean view. The Aloha Kai Suite is ...
  • Nightly
    $895 - $1,995
  • Weekly
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  • Monthly
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Contact Owner
Nightly rate from
$125
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 1, sleeps 3
Bathrooms: 1
Flooded with light and filled with birdsong, this second/top floor apartment has everything including privacy. At 750 sq ft with cathedral ceilings, it ...
  • Nightly
    $125 - $160
  • Weekly
    $875 - $1,120
  • Monthly
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Contact Owner
Nightly rate from
$995
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 3, sleeps 10
Bathrooms: 4
Our luxury ocean view town home is located in the gated community of Ho'olei, across the street from the Grand Wailea Resort. Our 3 bedroom/3bath home ...
  • Nightly
    $995 - $2,495
  • Weekly
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Contact Owner
Nightly rate from
$189
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Come enjoy our "PEACEFUL MAUI CONDO," unit 164... AVAILABLE DECEMBER 12-21, 2009 189 NIGHT!! Our Family-Friendly 2 Bedroom, 2 Bath Ocean & Fairway View condo ...
  • Nightly
    $189 - $295
  • Weekly
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Contact Owner
Nightly rate from
$405
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Beautifully remodeled and updated, our 1500 sf 2-Bedroom luxury condo in Wailea Resort's popular ocean front Wailea Ekahi Village is a few steps from ...
  • Nightly
    $405 - $485
  • Weekly
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  • Monthly
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Contact Owner
Nightly rate from
$125
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 1, sleeps 3
Bathrooms: 1
Spacious, elegant tropical modern apartment located in architecturally pleasing, low rise, individual buildings scattered amidst 12 tropical acres. Designer ...
  • Nightly
    $125 - $169
  • Weekly
    $875 - $1,120
  • Monthly
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Contact Owner
Nightly rate from
$99
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 1, sleeps 2
Bathrooms: 1
The TreeHouse Studio/Suite is a 2nd/top floor corner suite in the treetops. Surrounded by flowering tropical trees filled with birdsong, it feels more like a ...
  • Nightly
    $99 - $130
  • Weekly
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  • Monthly
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Contact Owner
Nightly rate from
$175
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 1, sleeps 4
Bathrooms: 2
Stay 7 nights and get the 8th night FREE! Winter Vacation Special!!! Book today for this great special! You won't find a better rate in all of Maui for a ...
  • Nightly
    $175 - $275
  • Weekly
    $1,225 - $1,925
  • Monthly
    $5,000 - $6,000
Contact Owner
Nightly rate from
$225
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
You will "LOVE OUR MAUI CONDO!" Unit 166... Completely remodeled and redecorated, our unit is CLEAN & QUIET! Our 2 bedroom/ 2 bath Ocean & Fairway View ...
  • Nightly
    $225 - $299
  • Weekly
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Contact Manager
Nightly rate from
$1,095
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 4
Floral Gardens Villa G102 is a new addition to the collection of extraordinary Wailea Beach Villas. Reservations are being accepted now. Floral Gardens was ...
  • Nightly
    $1,095
  • Weekly
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  • Monthly
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Contact Manager
Nightly rate from
$995
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 3
Blue Horizons Villa K308 is a newer addition to the collection of extraordinary Wailea Beach Villas. Outstanding views bless this extraordinary 3.5 bedroom ...
  • Nightly
    $995
  • Weekly
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  • Monthly
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Contact Manager
Nightly rate from
$595
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
YouTube Video Virtual Tour Wailea Beach Villas is an elite luxury retreat situated on the famous Wailea coastline on the island of Maui. Contact us about ...
  • Nightly
    $595 - $675
  • Weekly
    $4,165 - $4,865
  • Monthly
    $18,750 - $30,266
Contact Manager
Nightly rate from
$850
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 2
The aptly named Grand Seascape at Wailea Beach Villas, also known as "Penthouse/Tower Building K407", is a two bedroom plus den/alcove bedroom, two bath, ...
  • Nightly
    $850
  • Weekly
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  • Monthly
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Contact Manager
Nightly rate from
$245
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
A spacious two bedroom two bath condominium in beautiful Wailea. A partial ocean view, large barbeque grill and comfortable lanai furniture to enjoy while ...
  • Nightly
    $245 - $270
  • Weekly
    $1,540 - $1,715
  • Monthly
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Contact Manager
Nightly rate from
$675
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 4
Virtual Tour Ho'olei is located in the center of the best resort on the best island in the world. With its sunny, temperate climate, variety of activities, ...
  • Nightly
    $675
  • Weekly
    $4,725 - $14,875
  • Monthly
    $20,250 - $38,492
Wailea Vacation Rental Advice
Posted by copper350, Nov 16, 2009
... customiaze our meal. Whooooo........maui isn"t cheap though.I expect to get what I'm paying for hopefully. I thinking so much for one meal,but it's our dream vacation.I don't know when we'll be get ting back ,so I'm slurging.LOL Thanks! Copper ... more
Posted by copper350, Nov 17, 2009
... contract with him for next year. Need to workout our finances to do all that we wanted to do while on vacation,so I've been paying on thgs since Sept09. We are not rich,regular working people, but wanted a one in a lifetime vacation in maui. Thanks! Cooper ... more
Posted by yellowplumeria, Nov 19, 2009
... you land, pick up your rental car, get to the hotel, check in and unpack, you will be so tired that you will want a quick meal that night. I have been there many, many times and can tell you that you will be way too tired to enjoy a ... more
Posted by copper350, Nov 3, 2009
... insurance like $1200, but our vacation to maui next year with accomendations,airfare,tours,rental car,etc is in the thousands and we want to be protected just in case of anythg happens. This plan is fully loaded with what we choose. This also included cancel for any reason with ... more
Posted by MSRuby-7, Nov 3, 2009
... all our flights, hotels/condos, rental cars, and insurance through Continental Airlines. We selected accommodations and flight schedules for our four island tour. We came out better than we could have booking on our own. We booked through them because of the price and everything being insured. This will be ... more
Posted by Julauf, Oct 23, 2009
... and being able to turn around if you're not up for a long drive. Maui is one of those places where it's rare to stay in your resort for your entire vacation. There is so much to see and this rural island is pretty safe to travel around ... more
Posted by ChiSue, Oct 24, 2009
... while DH goes to the car rental. He then swings around to pick me up and off we go. That all takes about the same amount of time as the drive.( Enroute we stop at Safeway grocery to pick up a few things. It's to the right off Piilani ... more
Posted by Mommyoftwogoodkids, Oct 11, 2009
... of attemping to find a vacation rental for my parents' 40 year anniversary, my sister and my two kids 5 and 7. They are very good kids- but like to play and splash in the pool. After days of searching for affordable rentals I start to read the reviews about ... more
Posted by 7114, Oct 13, 2009
... but it will be a vacation to remember forever. Book your room on the hotel's website. You will be able to cancel easily. The list around here of stuff to do for kids is endless. The high cost of meals on Ka'anapali is not all that true. You ... more
Posted by MauiOC, Oct 4, 2009
... less expensive than going to the store as they can use CostCo and they don't get things that aren't on your list. To make life easier, http://www.mauiconcierge.com/ has expanded their personal services and are offering GROCERY STOCKING SERVICES (vacation rental provisioning) - see their SERVICES page ... more
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns