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Wailea Holiday Rentals

62 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 62
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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 - $449 night
$2093 - $4490 week


Non Smoking   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 #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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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 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
$280 - $370 night
$1960 - $2590 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: 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
$399 - $399 night
$1743 - $2793 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 Front
Condo: 2 Bedroom, 2 Bathroom, Sleeps 5
Location: Wailea, Hawaii, United States
Description: Wailea Elua #2110 - Gorgeous Ocean View 2 Bd 2 Ba - Great Rates! The Wailea Elua is the premier ocean front property in Wailea. Situated right on ... Learn More
Rates
$395 - $525 night
$2765 - $5250 week


Non Smoking


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2 bedroom Vacation Rental Condo in Wailea - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 5
Location: Wailea, Hawaii, United States
Description: Grand Champions #35 Ocean View 2R/2Br Upper Floor - Great Rates! Special Fall 2014 Rates - Please ask ! Grand Champions #35 is an inviting third ... Learn More
Rates
$240 - $285 night
$1505 - $1995 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: 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


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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 - $299 night
$1393 - $2990 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


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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


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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: Look no further! This open and spacious premium condo at The Palms at Wailea will be ideal for your island getaway! Major renovations throughout, a... Learn More
Rates
$250 - $330 night
$1610 - $2625 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
$284 - $284 night
$1393 - $2840 week


Non Smoking


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3 bedroom Vacation Rental Condo in Wailea
Condo: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: Wailea, Hawaii, United States
Description: Grand Champions 123 is located in a quiet setting in Wailea. Large green belts, manicured grounds and wide golf course fairways abound. To the east... Learn More
Rates
$220 - $300 night
$1400 - $2625 week


Non Smoking


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1 bedroom Vacation Rental Condo in Wailea
Condo: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Wailea, Hawaii, United States
Description: This luxury condo was designed to mirror a Balinese tree house. Completely remodeled with Hi-Tech Appliances. 2nd floor unit ~ stairs. 4 dining s... Learn More
Rates
$295 - $340 night
$2065 - $2520 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: Fall 2014 Discounted Rates. Please ask ! This second floor property has a fabulous view, charm, and is very convenient to the pool. Is is comforta... Learn More
Rates
$190 - $230 night
$1225 - $1610 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 ... Learn More
Rates
$295 - $495 night
$2065 - $4950 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: Stop! Look No Further! Palms at Wailea #1503 Ocean View Best Location! The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palm... Learn More
Rates
$299 - $449 night
$1890 - $3143 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 #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 - $399 night
$1743 - $2990 week


Non Smoking


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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
$225 - $299 night
$1575 - $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: This is a great property with a real tropical "Tommy Bahama" feel...Upscale furnishings and attention to detail complete this two bedroom two bath ... Learn More
Rates
$195 - $255 night
$1365 - $1785 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: 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
$179 - $299 night
$1253 - $2990 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: The Wailea Elua is the premier ocean front property in Wailea. Situated right on Ulua Beach, it has one of the best locations in Wailea. There are ... Learn More
Rates
$349 - $525 night
$2443 - $5250 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 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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