This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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Wailea Vacation Rentals Show this location only Back to top
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Amazing Oceanview! Wailea Ekolu 1BR/2BA - Air Conditioned
1BR+/2BA
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Sleeps 4
– Wailea Ekolu #33483
$160 - $200 per night 5 night min stay
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1 BR Treetop Luxury $140./nt
1BR/1BA
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Sleeps 2
– Grand Champions #28363
$140 - $169 per night 5 night min stay
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Luxury for Less! Enjoy the Ultimate Family Retreat and Vacation
3BR/3.5BA
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Sleeps 8
– Hoolei #134090
$595 - $1100 per night 3-7 night min stay
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Fantastically Remodeled Condo with Huge Dynamic Ocean Views
1BR+/2BA
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Sleeps 2-4
– Wailea Ekolu #19514
$260 - $280 per night 5 night min stay
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Beautiful Remodeled Wailea Gem! $140
1BR+/1BA
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Sleeps 4
– Grand Champions #26877
$140 - $180 per night 5 night min stay
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The Wailea Sunset Bungalow was Recently Re-Freshed with Live Green Plants, New Paint, Carpet, Drapery, Lamps, Solar Shades, and New Beautiful Solid Honey Teak Bedroom Furniture
2BR/1BA
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Sleeps 4
– Private Homes #40789
$650 - $950 per night
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Charming Private Studio! Renovated! May/June Specials $100/Night
Studio/1BA
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Sleeps 2
– Grand Champions #28298
$115- $140/nt
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Tropical Villa Vacations Exclusively Manages a Boutique Collection of More Than 20 of the Very Best Villas Within the Beachfront Wailea Beach Villas Resort
3BR/3BA
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Sleeps 6
– Wailea Beach Villas #29488
$1195 - $2350 per night
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Studio Super Special May 26-30 $420 Total 4 Nts
Studio/1BA
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Sleeps 2
– Grand Champions #33820
From $110/nt
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Luxurious Wailea Suite @ Kihei Rates!
Studio/1BA
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Sleeps 1-2
– Grand Champions #14408
$105- $125/nt
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Wailea Sunset Estate, One of Our Most Popular Vacation Homes, was Just Lovingly Refreshed with Some Upgraded Amenities and Decor
4BR/5.5BA
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Sleeps 8
– Private Homes #71812
$2500 - $4750 per night
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Upgrade to a Great Deal with Dazzling Aloha Contemporary Suite
2BR+/2BA
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Sleeps 6
– Wailea Beach Villas #108755
From $650 a night
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Summer Specials! Best Value Deluxe Ocean View Townhome!
3BR+/3.5BA
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Sleeps 6-8
– Hoolei #223871
$895 - $1495 per night 3-10 night min stay
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2BR/2BA Wailea Condo Reduced Rates May, June
2BR+/2BA
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Sleeps 6
– Grand Champions #57038
$160- $190/nt
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Magnificent Panoramic Views!! Gorgeous Private End Unit!!
2BR+/2BA
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Sleeps 4-6
– Grand Champions #26958
$195 - $280 per night 5-14 night min stay
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Tropical Villa Vacations Exclusively Manages a Boutique Collection of More Than 20 of the Very Best Villas Within the Beachfront Wailea Beach Villas Resort
3BR/2BA
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Sleeps 6
– Wailea Beach Villas #88884
$995 - $2250 per night
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Amazing Remodel, Walk to Beach, Check Reviews, Central Ac
2BR+/2BA
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Sleeps 6
– The Palms at Wailea #81055
$275 per night 5 night min stay
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Tropical Villa Vacations Exclusively Manages a Boutique Collection of More Than 20 of the Very Best Villas Within the Beachfront Wailea Beach Villas Resort
3BR/2BA
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Sleeps 6
– Wailea Beach Villas #92847
$795 - $1750 per night
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Treetop Studio from $110/Night
Studio/1BA
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Sleeps 2
– Grand Champions #202903
$110 - $129 per night 5 night min stay
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K308 Blue Horizons 4 Bedroom Ocean View Villa was Recently Updated, Upgraded and Refreshed Including Sparkling Polished Marble Floors, New Decor, Furniture, Wall Art, Lighting, State-of-Art Electronics Including Large Flat Panel Samsung Televisions, Live Plants, Rich Wool Area Rugs, Capiz Shell Chandelier, and Other Lux Details
4BR/3BA
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Sleeps 8
– Wailea Beach Villas #75446
$1595 - $3150 per night
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Special Offer 170 Per Night. Per 2 May Thru June.
2BR/2BA
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Sleeps 4
– Grand Champions #19843
185 - $200/nt
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"Best Vacation Ever" Say Our Guests! Luxurious & Affordable!
2BR/2BA
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Sleeps 4-6
– Grand Champions #3947
From $145/nt
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Tropical Villa Vacations Exclusively Manages a Boutique Collection of More Than 20 of the Very Best Villas Within the Beachfront Wailea Beach Villas Resort
3BR/3.5BA
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Sleeps 6
– Wailea Beach Villas #91603
$1595 - $3350 per night
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Ekahi 5a: Prime Location, Newly Remodeled, Well Equipped !!!
1BR+/2BA
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Sleeps 4-5
– Ekahi Village #39541
$260 to $400
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Tropical Villa Vacations Exclusively Manages a Boutique Collection of More Than 20 of the Very Best Villas Within the Beachfront Wailea Beach Villas Resort
4BR/3BA
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Sleeps 8
– Wailea Beach Villas #126958
$1450 - $3250 per night
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Wailea Beach Villas K107 - Stunning 2.5 Bedroom Paradise
2BR+/2BA
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Sleeps 6
– Wailea Beach Villas #113264
From $650/nt
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Wailea Elua Village Prime Oceanfront - the Best of the Best!
1BR+/1BA
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Sleeps 2-4
– Elua Village #51993
From $435/nt
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Polo Beach: Sunsational Penthouse Condo on its Soft Sand Beach
2BR/2BA
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Sleeps 4
– Polo Beach Club #27027
$559 - $759/nt
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Luxurious Ocean Front Condo - Exclusive Location in Wailea
2BR+/2BA
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Sleeps 4-6
– Polo Beach Club #22111
$295- $795/nt
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Tropical Villa Vacations Exclusively Manages a Boutique Collection of More Than 20 of the Very Best Villas Within the Beachfront Wailea Beach Villas Resort
3BR/3.5BA
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Sleeps 6
– Wailea Beach Villas #154149
$1995 - $3950 per night
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Enjoy Dinner and Wine on the Beach for a Maui Sunset Treat!
2BR+/2BA
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Sleeps 8
– Ekahi Village #71926
$385- 415/nt
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Wailea Home W/ Private Tennis Ct Steps from Keawakapu Bch
3BR/2BA
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Sleeps 6
– Other Wailea Properties #262763
$350 - $550 per night 5-7 night min stay
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Grand Champion Villas / Partial Ocean View on Golf Course
2BR+/2BA
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Sleeps 6
– Grand Champions #59147
$185- $250/nt
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Closest to the Beach and Pool! Location, Location!!
3BR+/3.5BA
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Sleeps 8
– Hoolei #227809
$650 - $1750 per night 5-10 night min stay
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J305 Aqua Lani at Wailea Beach Villas was the Featured Property in a Story About Upscale Villas Managed by Tropical Villa Vacations on Maui in the October 24, 2010 Issue of the San Francisco Sunday Examiner
3BR/3BA
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Sleeps 6
– Wailea Beach Villas #199396
$1195 - $2450 per night
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Grand Chamapions #48 Great Ocean Views! 2bd 2 BA Great Rates!!
2BR/2BA
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Sleeps 2-6
– Grand Champions #246671
$174 - $299 per night
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Tropical Villa Vacations Exclusively Manages a Boutique Collection of More Than 20 of the Very Best Villas Within the Beachfront Wailea Beach Villas Resort
3BR/3.5BA
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Sleeps 6
– Wailea Beach Villas #111268
$1295 - $2750 per night
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Beachfront, Polo Beach Wailea/Makena #204 - Accommodates 2-7
2BR+/2BA
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Sleeps 4-7
– Polo Beach Club #5224
$300- $895/nt
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Wailea Ekolu Oceanview 2BR/2BA - Ground Floor
2BR/2BA
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Sleeps 4
– Wailea Ekolu #19953
From $170/nt
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Wow!! Beautifully Decorated! Fully Air-Conditioned! Near Pool!
2BR+/2BA
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Sleeps 4-6
– The Palms at Wailea #49477
From $245/nt
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Palms 904 Lanai Overlook Garden, Ocean & Mountains. Walk to Beach
2BR+/2BA
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Sleeps 6
– The Palms at Wailea #331601
$243 - $414 per night 5-7 night min stay
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Ekahi 6b - Amazing Location, 1 Min to Beach & Pool, Email Now!
1BR+/2BA
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Sleeps 2-4
– Ekahi Village #88450
From $245/nt
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Luxury Ocean View, Sleeps 10 $595 Special Rate May 19-30, 2013
3BR+/3.5BA
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Sleeps 8-10
– Hoolei #223642
$650 - $1650 per night 2-5 night min stay
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Amazing Wailea Surf Villa: Luxury 2BR/2BA Owner Direct - *See Specials*
2BR+/2BA
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Sleeps 6
– Wailea Beach Villas #277930
From $595/nt
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J205: Our Aloha Kai Suite. Exquisite 3BR/3BA with Ocean View!
3BR+/3BA
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Sleeps 6-8
– Wailea Beach Villas #122885
From $895/nt
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Tropical Villa Vacations Exclusively Manages a Boutique Collection of More Than 20 of the Very Best Villas Within the Beachfront Wailea Beach Villas Resort
3BR/3.5BA
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Sleeps 6
– Wailea Beach Villas #89097
$2650 - $5000 per night
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Absolutely Gorgeous, Affordable, Luxurious Spacious Condo
2BR+/2BA
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Sleeps 4-9
– The Palms at Wailea #204169
$215- $325/nt
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C301 Sun Splash Villa is a New Vacation Villa Rental Opportunity Within the Wailea Beach Villas, a Residential Villa Resort Set Directly on Wailea Beach in Wailea Resort, on the Leeward Sunny Side of Maui Island
3BR/3.5BA
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Sleeps 6
– Wailea Beach Villas #95063
$1750 - $3950 per night
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Tropical Villa Vacations Exclusively Manages a Boutique Collection of More Than 20 of the Very Best Villas Within the Beachfront Wailea Beach Villas Resort
3BR/2BA
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Sleeps 6
– Wailea Beach Villas #211582
$1095 - $2350 per night
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Spectacular Sunset Ocean View in Peaceful Wailea - Hd Hbo/Sho
1BR+/2BA
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Sleeps 2-4
– Wailea Ekolu #135092
$250 - $335 per night 3-7 night min stay
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Get it All! December 20th - 27th 2013 Available!
1BR+/2BA
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Sleeps 2-4
– Wailea Ekolu #102610
$200- $275/nt
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Renting a Vacation Lifestyle, Not Just a Home
3BR/3BA
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Sleeps 6
– Hoolei #312581
$4550 - $12250 per week 7 night min stay
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Elua Village-2 BR, Ground Floor Ocean View Condo-1528 Sq Ft.
2BR+/2BA
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Sleeps 6
– Elua Village #30630
$395/nt
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2BR 2BA, Ocean View in Beautiful Wailea.
2BR/2BA
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Sleeps 2-4
– Grand Champions #243486
$175- $275/nt
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Mana Kai Resort, Directly on Maui's Best Beach, Oceanfront!!
2BR+/2BA
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Sleeps 4-6
– Other Wailea Properties #32997
From $310/nt
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The Maui Escape - Spectacular 2.5 Bdr Penthouse- Owner Direct!
2BR+/2BA
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Sleeps 6
– Wailea Beach Villas #131603
From $700/nt - $4900/wk
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Ocean View, Remodeled, Stuff for Kids, Clean
2BR+/2BA
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Sleeps 6
– Grand Champions #72830
$250 - $325 per night 4-7 night min stay
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Wailea - Luxury, Comfort and Beachfront Living at Polo Beach Club #408
2BR/2BA
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Sleeps 4
– Polo Beach Club #71367
$595 - $750 per night 2-14 night min stay
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Remodeled with Ocean View. Enough Said!
2BR+/2BA
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Sleeps 4-6
– Ekahi Village #124276
$395- $500/nt
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Tropical Villa Vacations Exclusively Manages a Boutique Collection of More Than 20 of the Very Best Villas Within the Beachfront Wailea Beach Villas Resort
3BR/3.5BA
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Sleeps 6
– Wailea Beach Villas #211581
$1495 - $2950 per night
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Now Till Summer $135/nt!! Beautifully Remodeled! Very Private!
1BR+/2BA
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Sleeps 2-4
– Grand Champions #164191
From $135/nt
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New Remodel, New Calif King Bed, Ocean/Mountain/Garden/ Views
1BR+/2BA
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Sleeps 2-4
– Ekahi Village #211243
$183 - $285 per night 5 night min stay
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Gorgeous Oceanfront Newly Remodelled North End of Keawakapu
2BR/2BA
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Sleeps 4
– Other Wailea Properties #112036
$255 - $485/nt United States Dollars
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Panoramic Ocean Views! - * See Specials! * - 3 Bed/3 Bath
3BR+/3BA
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Sleeps 8
– Wailea Beach Villas #342422
From $850/nt
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Tropical Villa Vacations Exclusively Manages a Boutique Collection of More Than 20 of the Very Best Villas Within the Beachfront Wailea Beach Villas Resort
5BR/3BA
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Sleeps 6
– Wailea Beach Villas #279557
$1695 - $3350 per night
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Luxury Living with Sophistication at Hoolei! *****Five Star Reviews! 3BR/3.5BA – Sleeps 6 – Hoolei #252601
Special offer JUNE SPECIALS!!!
May 25, 2013 to Jun 25, 2013
$650 - $1750 per night 5-10 night min stay -
The Change You Are Looking for!
1BR+/1BA
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Sleeps 2-4
– Ekahi Village #166545
$295- $395/nt
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Gorgeous Ocean View, Beautifully Remodeled and Decorated
2BR+/2BA
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Sleeps 6
– Ekahi Village #200128
$375 - $425 per night 6 night min stay
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Luxury 2BR, Ocean View, Owner Direct - Read Our Guest Reviews!
2BR/2BA
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Sleeps 5
– Elua Village #203468
$395 - $485 per night
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High End Spectacular Oceanfront Avail Aug 17-26 & Sept 22-28!
1BR+/1.5BA
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Sleeps 4
– Other Wailea Properties #257679
$155 - $295/nt
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Beautifully Renovated with Modern Decor 2 Bedroom 2 Bathroom
2BR/2BA
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Sleeps 4
– Grand Champions #286927
From $160/nt
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Premium Ocean Hibiscus 23-1 (Biggest) Fr $645
3BR+/3.5BA
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Sleeps 6-8
– Hoolei #224781
From $645
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Rare 3BR Grand Champions Villa with Full Ocean View
3BR+/2BA
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Sleeps 7
– Grand Champions #46093
From $285/nt + disc for 14+ nts
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Very Best Deluxe Ocean View...Panoramic View....First Class!!
3BR+/3.5BA
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Sleeps 6-8
– Hoolei #304656
$650- $1500/nt
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2 Bd/2 BA Wailea Condo with 180 Degrees Superior Ocean View;
2BR+/2BA
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Sleeps 4
– Wailea Ekolu #233457
$250 - $295 per night 5 night min stay
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Couples Special, $165.00 a nt. for June and July 2013. Five Minute Walk to Beach
1BR+/2BA
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Sleeps 1-4
– Ekahi Village #125120
$175.00/ $250.00
- Wailea Ekahi 2a, Lower Village, 2BR/2BA, Spectacular Ocean Views and Sunsets 2BR/2BA – Sleeps 6 – Ekahi Village #100688
- Ho'Olei in Wailea - Always Providing Excellent Service and Value! 3BR/3.5BA – Sleeps 10 – Hoolei #252600
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Owner Direct - Wailea Elua Oceanfront, Fully Renovated
2BR+/2BA
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Sleeps 4-6
– Elua Village #257933
$695- $995/nt
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Upgraded! Top Floor! Beautiful Ocean & Fairway Views! Romance!
1BR+/2BA
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Sleeps 2
– Grand Champions #125492
From $160/nt
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Best Ocean & Island Views ~ Top Floor Penthouse ~ Why Compromise
2BR+/2BA
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Sleeps 6
– Wailea Beach Villas #306836
$875 - $1850 per night 5-10 night min stay
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Awesome Ocean View - Beautiful 2 BR/2.5 BA Wailea Ekahi Condo
2BR+/2.5BA
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Sleeps 4-6
– Ekahi Village #51926
$375- $425/nt
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All You Need is Your Bathing Suit...
2BR+/2BA
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Sleeps 6
– Grand Champions #109065
From $169/night
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Wailea Ekolu Spectacular 2 Bd 2.5 Bath Deluxe Ocean View Townhouse Sleeps 4
2BR/2.5BA
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Sleeps 4
– Wailea Ekolu #360006
$284 - $449 per night
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Hawaiian Escape -Blue Golf Course *Call for Travel Specials*
1BR/2BA
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Sleeps 2-4
– Grand Champions #12177
$125- $150/nt US Dollars Only
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Incredibly Large Palms at Wailea Polynesian Style Villa
2BR+/3BA
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Sleeps 4-6
– The Palms at Wailea #262887
$295 - $375 per night 4-7 night min stay
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Wailea Beachfront! Ocean and Garden Views, Private Location
1BR+/1BA
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Sleeps 4
– Ekahi Village #325317
From $225/nt
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Wailea Beach Villa! Luxury 2.5 BR *See Specials* $550-$1100!
2BR+/2BA
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Sleeps 6
– Wailea Beach Villas #102890
From $550/nt - $3850/wk
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Panoramic Ocean View - Luxury in Paradise - Hi Tax Id W0650372101
2BR/2BA
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Sleeps 4
– Ekahi Village #153440
$3465 - $3850 per week 7 night min stay
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25d - Sunny Lower Ekahi Village Condo!
1BR+/1BA
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Sleeps 2-4
– Ekahi Village #363297
$165 - $280 per night 1-14 night min stay
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Wow! Completely Remodeled! Fabulous Ocean Views! Top Floor!!
2BR+/2BA
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Sleeps 5-6
– Grand Champions #154905
$200- $240/nt
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May June July**Specials-Spectacular Ocean View, Stuff for the Kids
1BR/2BA
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Sleeps 4
– Ekahi Village #184515
$2030 - $2275 per week 7 night min stay
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Starting $125/nt! Beautiful Ocean & Fairway Views! Top Floor!
1BR+/2BA
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Sleeps 2-3
– Grand Champions #86219
From $145/nt
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Wailea Ekahi - Oceanview Studio and 1 BR Condos on Greenbelt
1BR+/1BA
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Sleeps 4
– Ekahi Village #244703
From $175/nt
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The Perfect Escape! Ho'Olei Dream Home-Super Close to Pool
3BR/3.5BA
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Sleeps 8
– Hoolei #288245
$895 per night 5 night min stay
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Huge Savings for Ocean Villa Trip Advisor Says Perfect L409
4BR+/3BA
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Sleeps 2-10
– Wailea Beach Villas #137977
$1250 - $2400 per night 5-7 night min stay
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Views Views Views Ekolu Village Remodel - Child Friendly
2BR+/2BA
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Sleeps 6
– Wailea Ekolu #103796
$255- $315/nt
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Ekahi Village, Wailea - Maui a Place Apart Condominimums!
1BR+/2BA
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Sleeps 2-4
– Ekahi Village #119557
$145- $350/nt
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Fabulous Ocean & Fairway Views! Top Floor 3 BR @ Great Price!!
3BR+/2BA
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Sleeps 4-8
– Grand Champions #125596
$255/nt
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Spacious 2.5 Bedroom with Spectacular Lanai Overlooking Pool
2BR+/2.5BA
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Sleeps 6
– Wailea Beach Villas #385930
$895 per night 5 night min stay
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Amazing Oceanview! Wailea Ekolu 1BR/2BA - Air Conditioned
1BR+/2BA
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Sleeps 4
– Wailea Ekolu #33483
Overview of Wailea Vacation Rentals
Discover the Beauty of Nature Surrounding Wailea Vacation Rentals
Step away from your office and feel the stress leave you as you stay in Wailea vacation rentals. Feel the sun warm you and smell the tropical flowers surrounding you as you stroll along the boardwalk or on the beach. As you inhale, you can smell the salt water and listen to the waves crash onto the shoreline as you collect shells and driftwood. Feel anxiety slip away as you sit on your porch and watch the sun set over the beautiful southern Maui waters.
There's Something for Everyone When Staying in Wailea Condos
When you stay in Wailea condos, you are really adding dimension to a tropical vacation. Instead of crowding into a stuffy hotel room, you can spread out in a house with multiple bedrooms and bathrooms. If you want, you can pick up some fresh foods at the nearby shops at Wailea or walk over to some nearby restaurants. Catch a quick lunch at Ferraro's Bar e Ristorante or head over to Spago for a romantic dinner. Live like a local as you participate in holiday celebrations while staying at Wailea condos.
South Maui Beach Rentals Keep You Close to Popular Tourist Attractions
If you feel like taking a break from snorkeling, swimming, and sailing, consider spending a day at the Wailea Old Blue Golf Course. Top the day off with a luau celebration that your entire family can enjoy. Watch traditional dancers and listen to ukulele players as you eat tropical fruit and other local foods. Stretching your legs has never been quite so enjoyable as when you set out on a path through a tropical rainforest or on the Coastal Nature Trail. If you travel between December and April, gather your family and friends for some magnificent whale watching.