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Wailea Holiday Rentals

63 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 63
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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... Learn More
Rates
$299 - $399 night
$2093 - $4490 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 #1508 Panroamic Ocean Views 2/2 Sleeps 6 Great Rates The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms ... Learn More
Rates
$1743 - $3990 week


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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... Learn More
Rates
$252 - $370 night
$1764 - $2590 week


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2 bedroom Vacation Rental Condo in Wailea
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States
Description: Special Fall 2014 Rates - Please ask ! Beautifully decorated and fully renovated two bedroom condominium with garden, some ocean and mountain view... Learn More
Rates
$275 - $325 night
$1680 - $2275 week


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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 #163 2Br/2Ba Convenient 1st Floor Location. 2011 Remodel! Special Fall 2014 Rates! Please inquire. Grand Champions 163 is a deligh... Learn More
Rates
$275 - $325 night
$1680 - $2275 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... Learn More
Rates
$750 - $2400 night


Non Smoking   Handicap Accessible   Swimming Pool   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 #1101 Great Ocean Views! Large Sun Deck! 2/2 Great Rates! The fabulous Keawakapu Beach is just a short 10 minute stroll from the P... Learn More
Rates
$249 - $349 night
$1743 - $2990 week


Non Smoking


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3 bedroom Vacation Rental Condo in Wailea - Ocean View
Condo: 3 Bedroom, 4 Bathroom, Sleeps 8
Location: Wailea, Hawaii, United States
Description: Ho'olei #39-3 'Ocean's Invitation' Premier Location and View ! Fall 2014 - Super Special Rates for Ocean's Invitation! Please Inquire by E-Mail or... Learn More
Rates
$5495 - $11165 week


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1 bedroom Vacation Rental Condo in Wailea - Ocean View
Condo: 1 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States
Description: Palms at Wailea #307 Remodeled and Beautifully Furnished 1 Bd 2 Ba Sleeps 4! The fabulous Keawakapu Beach is just a short 10 minute stroll from th... Learn More
Rates
$179 - $179 night
$1253 - $2840 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 Great Rates! The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wa... Learn More
Rates
$199 - $299 night
$1393 - $2990 week


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2 bedroom Vacation Rental Condo in Wailea
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States
Description: Palms at Wailea - 2B/2B Fully Remodeled. Close to World-Class Beaches! The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palm... Learn More
Rates
$299 - $399 night
$2093 - $4490 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 #1406 Panoramic Ocean Views 2Bd 2Bath Great Rates! The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at... Learn More
Rates
$199 - $299 night
$1393 - $2990 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: Wailea Grand Champions #50 is a 2 Bd 2 Ba Upgraded Unit. It can sleep 6. The nearby Ulua and Mokapu Beaches are a quick drive down the hill from T... Learn More
Rates
$199 - $224 night
$1393 - $2990 week


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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 2014 Fall Rates - Please Ask ! Grand Champions 49 is perfect ... Learn More
Rates
$240 - $285 night
$1505 - $1995 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in Wailea - Ocean Front
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States
Description: Wailea Elua #2105 Spring Special Rate $325 Sleeps 6 Oceanview~ The Wailea Elua is the premier ocean front property in Wailea. Situated right on Ul... Learn More
Rates
$325 - $349 night
$2275 - $5250 week


Non Smoking


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3 bedroom Vacation Rental Condo in Wailea - Ocean View
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... Learn More
Rates
$299 - $299 night
$2093 - $6050 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: 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... Learn More
Rates
$209 - $279 night
$1463 - $2990 week


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2 bedroom Vacation Rental Condo in Wailea - Ocean View
Condo: 2 Bedroom, 3 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States
Description: Wailea Ekolu #314 Spectacular Ocean View 2 Bd 2.5 Bath Townhouse Sleeps 4! Unit #314 at Wailea Ekolu is the one of the most outstanding properties... Learn More
Rates
$284 - $349 night
$1988 - $4490 week


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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... Learn More
Rates
$795 - $1500 night
$5565 - $10500 week


Swimming Pool   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: Palms at Wailea Unit #2305 Quiet, Clean and Very Private! Great Rates!! We are pleased that our properties at the Palms at Wailea have been chosen... Learn More
Rates
$159 - $249 night
$1113 - $2790 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: Stunning 1-BR Condo Fully Remodeled on a World-Class Golf Course. Grand Champions 181 is located in a quiet setting in Wailea. Large green belts, ... Learn More
Rates
$139 - $190 night
$875 - $1610 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 Fall 2014 Specials. Grand Champions 186 is ... Learn More
Rates
$240 - $285 night
$1505 - $1995 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: Grand Champions #165, 2Br/2Ba On The Golf Course - Great Rates! Special 2014 Rates Please Ask! The inviting tropical decor in Grand Champions 165 ... Learn More
Rates
$240 - $285 night
$1505 - $1995 week


Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Condo in Wailea
Condo: 3 Bedroom, 4 Bathroom, Sleeps 8
Location: Wailea, Hawaii, United States
Description: Fall 2014 Specials - Please ASK! Relax in this spectacular three bedroom deluxe accommodation. Beautiful decorations, with an inviting atmosphere w... Learn More
Rates
$4795 - $10115 week


Non Smoking   High-Speed Internet


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1 bedroom Vacation Rental Condo in Wailea - Ocean View
Condo: 1 Bedroom, 2 Bathroom, Sleeps 4
Location: Wailea, Hawaii, United States
Description: Wailea Ekolu #804 Best Panoramic Ocean View 1Bd 2Ba Private location! Wailea Ekolu is one of most sought after properties in Wailea as it is nestl... Learn More
Rates
$199 - $289 night
$1393 - $3490 week


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