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Wailea Holiday Rentals

65 Wailea Holiday Rentals were found matching your criteria. These vacation rentals are presented by their owners or managers. Please click on the photos or links below, then contact them directly with your inquiries. Use the search criteria box on the left of the page to refine your search within Wailea, Maui, Hawaii, United States.
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Listings 1 - 25 of 65
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2 bedroom Vacation Rental Condo in Wailea
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States
Description: Wailea Ekahi - Nicely appointed 2 bedroom, 2 bath condo with garden and partial oceanview in the Upper Village over looking the top pool. Kitchen a...
Rates
$266 - $370 night
$1862 - $2590 week


Non Smoking   High-Speed Internet


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Featured


2 bedroom Vacation Rental Condo in Wailea
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States
Description: Grand Champions #163 2Br/2Ba Convenient 1st Floor Location. 2011 Remodel! Special Fall 2015 Rates! Please inquire. Grand Champions 163 is a deli...
Rates
$285 - $285 night
$1750 - $2345 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in Wailea - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States
Description: Palms at Wailea #1105 Oceanview Completely Remodeled 2Bd 2Bath Great Rates! The fabulous Keawakapu Beach is just a short 10 minute stroll from the...
Rates
$299 - $439 night
$2093 - $4490 week


Non Smoking


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Featured


2 bedroom Vacation Rental Condo in Wailea - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States
Description: Palms at Wailea #1508 Panroamic Ocean Views 2/2 Sleeps 6 Great Rates The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms ...
Rates
$1743 - $3990 week


Non Smoking


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Featured


2 bedroom Vacation Rental Condo in Wailea
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States
Description: Special Fall 2015 Rates - Please ask ! Beautifully decorated and fully renovated two bedroom condominium with garden, some ocean and mountain view...
Rates
$285 - $285 night
$1750 - $2345 week


Non Smoking   High-Speed Internet


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4 bedroom Vacation Rental Villa in Wailea - Ocean View
Villa: 4 Bedroom, 3 Bathroom, Sleeps 10
Location: Wailea, Hawaii, United States
Description: Most popular Maui Condo Wailea Beach Villa L409 Rated Perfect on Trip Advisor. 4BR (3 Kings/1 Queen, or 2 Kings/ 2 Twins/1 Queen) 3 BA villa . Spec...
Rates
$750 - $2400 night


Non Smoking   Handicap Accessible   Swimming Pool   High-Speed Internet


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2 bedroom Vacation Rental Condo in Wailea
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States
Description: Grand Champions #102 2Br/2Ba Golf Course and Mountain Views - Best Rates Fall 2015 Special Rates - Please Ask ! Grand Champions #102, located on...
Rates
$250 - $250 night
$1575 - $2065 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in Wailea - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States
Description: Wailea Ekolu #1108 2 Bd. 2Ba. Premier Ocean View! $215 Summer Special! Wailea Ekolu is one of most sought after properties in Wailea as it is nest...
Rates
$215 - $325 night
$1505 - $3950 week


Non Smoking


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2 bedroom Vacation Rental Condo in Wailea - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States
Description: Palms at Wailea #1204 Ocean View 2Bd 2 Ba Sleeps 4. $199 Summer Special! The fabulous Keawakapu Beach is just a short 10 minute stroll from the Pa...
Rates
$199 - $329 night
$1393 - $3240 week


Non Smoking


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2 bedroom Vacation Rental Condo in Wailea - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States
Description: Wailea Ekolu #501 Panoramic Ocean View, Renovated! $179 Summer Special! Wailea Ekolu is one of most sought after properties in Wailea as it is nes...
Rates
$179 - $329 night
$1253 - $3950 week


Non Smoking


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2 bedroom Vacation Rental Condo in Wailea
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States
Description: Grand Champions #186 2Br/2Ba Near The Pool, Great Location and many Upgrades. Please ask us about our Summer and Fall 2015 Specials. Grand Champi...
Rates
$250 - $250 night
$1575 - $2065 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in Wailea
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States
Description: The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach is world famous for its great snorkeling and lon...
Rates
$159 - $329 night
$1113 - $3240 week


Non Smoking


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2 bedroom Vacation Rental Condo in Wailea
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States
Description: This is a great property with a real tropical "Tommy Bahama" feel...Upscale furnishings and attention to detail complete this two bedroom two bath ...
Rates
$195 - $255 night
$1365 - $1785 week


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1 bedroom Vacation Rental Condo in Wailea - Ocean View
Condo: 1 Bedroom, 2 Bathroom, Sleeps 2
Location: Wailea, Hawaii, United States
Description: Relax in the casual comfort of this recently renovated 1 bedroom / 2 bath unit. Its interior is spacious and serene, with a touch of Asian tranquil...
Rates
$225 - $303 night
$1575 - $2890 week


Non Smoking


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1 bedroom Vacation Rental Condo in Wailea
Condo: 1 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States
Description: Wailea Ekahi Village - 1 bedroom, 2 bath condo with a calming garden view located in the Upper Village. New King size bed, sofa sleeper, air condi...
Rates
$190 - $250 night
$1330 - $1750 week


Non Smoking   High-Speed Internet


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1 bedroom Vacation Rental Condo in Wailea
Condo: 1 Bedroom, 2 Bathroom, Sleeps 2
Location: Wailea, Hawaii, United States
Description: Fall 2015 Special Rates!!! As soon as you enter you?ll see the 7th fairway of the golf course with the Ocean in the distance. The condo is on the...
Rates
$185 - $185 night
$1190 - $1785 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in Wailea - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States
Description: Palms at Wailea #1606 Spacious 2Br/2Ba - Great Rates - Free Wifi ! Special Fall 2015 Rates. Please Ask ! A spacious two bedroom two bath condomi...
Rates
$245 - $245 night
$1540 - $1995 week


Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Condo in Wailea - Ocean View
Condo: 3 Bedroom, 3.5 Bathroom, Sleeps 8
Location: Wailea, Hawaii, United States
Description: Ho'olei #39-3 'Ocean's Invitation' Premier Location and View ! Enjoy more than 2700 feet of comfortable yet lavish, uniquely and professionally de...
Rates
$5670 - $11165 week


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2 bedroom Vacation Rental Condo in Wailea - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States
Description: This 2-bedroom condo is comfortably appointed, and located in a great spot on property. The spacious living room opens to the Lanai, where there is...
Rates
$150 - $320 night
$980 - $2450 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in Wailea - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States
Description: Palms at Wailea #1102 Probably the best ocean view at the Palms at Wailea! The fabulous Keawakapu Beach is just a short 10 minute stroll from the ...
Rates
$295 - $435 night
$2065 - $4950 week


Non Smoking


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1 bedroom Vacation Rental Condo in Wailea
Condo: 1 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States
Description: Palms at Wailea 702 Upstairs Garden View 1Bd 2Ba Sleeps 4 Great Rates! The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palm...
Rates
$189 - $279 night
$1323 - $2990 week


Non Smoking


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2 bedroom Vacation Rental Condo in Wailea
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States
Description: Grand Champions #49 - Ground Floor, Corner Location with Easy Pool Access ! Special 2015 Fall Rates - Please Ask ! Grand Champions 49 is perfect ...
Rates
$250 - $250 night
$1575 - $2065 week


Non Smoking   High-Speed Internet


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1 bedroom Vacation Rental Condo in Wailea
Condo: 1 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States
Description: Palms at Wailea 609 Ground Level Garden View - 1Bd 2Ba Sleeps 4: Great Rates! The fabulous Keawakapu Beach is just a short 10 minute stroll from t...
Rates
$169 - $269 night
$1183 - $2890 week


Non Smoking


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3 bedroom Vacation Rental Condo in Wailea
Condo: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Wailea, Hawaii, United States
Description: Grand Champions #143 is a 3 BR 2 bath renovated golf course view condo. Unit 143 at the Wailea Grand Champions is a RARE 3 bedroom 2 bath unit wit...
Rates
$299 - $299 night
$2093 - $6050 week


Non Smoking


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3 bedroom Vacation Rental Condo in Wailea - Ocean View
Condo: 3 Bedroom, 3 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States
Description: The “crown jewel” of Wailea- A gated beachfront location, an oceanfront adult pool with a Jacuzzi, a children’s pool with a Jacuzzi in a garden s...
Rates
$795 - $1500 night
$5565 - $10500 week


Swimming Pool   High-Speed Internet


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