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Wailea Romantic Villas

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0+ rooms, 2+ guests
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$1,000+
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46 rentals in Wailea.
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Regal Mandalay M511 Wailea Beach Villas
3 bedrooms
2 bathrooms
Sleeps 6
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Golden Mandarin D102 Wailea Beach Villas
3 bedrooms
4 bathrooms
Sleeps 6
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Blue Horizons K308 Wailea Beach Villas
4 bedrooms
3 bathrooms
Sleeps 8
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Grand Champions #48: Stunning 180 Degree Ocean Views. Top Floor Paradise Home
2 bedrooms
2 bathrooms
Sleeps 6
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7 other travelers have booked this property
Maui Rendezvous Wailea Ekahi 33A Luxury Resort, Beach - 3 min. walk, Remodeled
1 bedroom
2 bathrooms
Sleeps 5
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4 other travelers have booked this property
Ekahi 36a 1Br 2Ba condo sleeps 4, Fully Renovated
1 bedroom
2 bathrooms
Sleeps 4
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Sandcastles Suite L509 Wailea Beach Villas
4 bedrooms
3 bathrooms
Sleeps 8
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Outstanding Luxury Condo for Couples in Paradise - Ocean and Beacfront
1 bedroom
1 bathroom
Sleeps 2
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8 other travelers have booked this property
Bali Hai Pool Villa F102 at Wailea Beach Villas
3 bedrooms
4 bathrooms
Sleeps 6
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OCEAN VIEW PRIVATE ROMANTIC COTTAGE ABOVE WAILEA
1 bedroom
2 bathrooms
Sleeps 3
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41 other travelers have booked this property
Grand Champions #45 is a 2bd 2ba Ocean view condo that Sleeps 6 Great Rates!
2 bedrooms
2 bathrooms
Sleeps 6
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8 other travelers have booked this property
Romantic, Elegant, Sensual Retreat
1 bedroom
2 bathrooms
Sleeps 2
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1 other traveler has booked this property
Intimate Tropical Retreat
1 bedroom
2 bathrooms
Sleeps 2
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Remodeled Mountain View 2 BDRM Condo - Royal Mauian #601
2 bedrooms
2 bathrooms
Sleeps 6
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Fantastic Wailea Ekahi Beachfront Condo 45F
1 bedroom
1 bathroom
Sleeps 5
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VACATION IN YOUR OWN PRIVATE MAUI PARADISE! Regal Mandalay M511, Panoramic Ocean
3 bedrooms
2 bathrooms
Sleeps 6
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Golden Mandarin Pool Villa D102 with Private Plunge Pool
3 bedrooms
4 bathrooms
Sleeps 6
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Stunningly Remodeled Ocean View Unit -Wailea Ekahi #22D
1 bedroom
2 bathrooms
Sleeps 4
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Beautiful Wailea Condo Wailea Ekolu # 312
1 bedroom
2 bathrooms
Sleeps 4
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Newly Remodeled Spacious Ground Floor Unit -Wailea Ekahi #22B
1 bedroom
2 bathrooms
Sleeps 4
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Remodeled 3BD w/AC - Great Location - Royal Mauian #302
3 bedrooms
2 bathrooms
Sleeps 8
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South Kihei Paradise & Great Location
2 bedrooms
2 bathrooms
Sleeps 6
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Renovated Maui Banyan Complex; Walk to Kam II Beach; Modern Kitchen!
2 bedrooms
2 bathrooms
Sleeps 6
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Beautiful Remodeled 2 BR/2 BA Condo in Luxurious Maui Kamaole
2 bedrooms
2 bathrooms
Sleeps 6
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Grand Champions 108, 1 Bedroom, Cozy Lanai, Pool Access, Hot Tub, Sleeps 2
1 bedroom
2 bathrooms
Sleeps 2
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Immaculate, Luxury Comfort, Stunning Views - Hawaiian-Chic, Mid-Century Modern
1 bedroom
2 bathrooms
Sleeps 2
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Generous size rooms & lanai make for a great stay at the Palms at Wailea 4033582
2 bedrooms
2 bathrooms
Sleeps 6
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Palms at Wailea 3033580 will be your new favorite! Clean & beautifully remodeled
2 bedrooms
2 bathrooms
Sleeps 6
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Grand Champions 87 golf-front condo w/ocean view, lanai & shared pool/hot tub!
2 bedrooms
2 bathrooms
Sleeps 4
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Wailea Ekahi 37C - 1 Bedroom
1 bedroom
2 bathrooms
Sleeps 4
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Beautiful Ocean Views- Stunning Location-Royal Mauian#416
2 bedrooms
2 bathrooms
Sleeps 4
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9B EKAHI VILLAGE-ONE BEDROOM/BATH, GARDEN VIEW - 1 MINUTE STROLL TO BEACH!
1 bedroom
1 bathroom
Sleeps 2
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Ocean Views -Remodeled Top Floor 2bd/2ba Condo - Kamaole Nalu #603
2 bedrooms
2 bathrooms
Sleeps 5
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I.P.M PRESENTS: Penthouse J105 - Perfect Location and Amazing Rates!
3 bedrooms
3 bathrooms
Sleeps 7
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Kihei Surfside · Breathtaking Oceanfront Gem in Kihei
1 bedroom
1 bathroom
Sleeps 4
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Kamaole Sands 5-313
1 bedroom
2 bathrooms
Sleeps 4
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Kamaole Sands 8-203
1 bedroom
2 bathrooms
Sleeps 4
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Grand Champions 124
1 bedroom
2 bathrooms
Sleeps 8
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Amazing view, Closest to the beach, Wailea Ekahi, Unit 20i.
1 bedroom
2 bathrooms
Sleeps 4
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Enjoy the Amazing View and have a Mai Tai too!
1 bedroom
2 bathrooms
Sleeps 4
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Gorgeous Ocean front view from your balcony! - Kihei Surfside #608
1 bedroom
1 bathroom
Sleeps 3
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Gorgeous Ocean front view from your balcony! - Kihei Surfside #608
1 bedroom
1 bathroom
Sleeps 3
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Snorkel at Kam Beach Steps From Chic Resort Condo!
2 bedrooms
2 bathrooms
Sleeps 4
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Oceanfront Location - Amazing Views - Kamaole Nalu #204
2 bedrooms
2 bathrooms
Sleeps 6
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Beautiful Remodeled Ocean View Condo -Wailea Ekahi #22E
1 bedroom
2 bathrooms
Sleeps 4
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Beautiful Remodeled Beach Front 2 Bed. Unit-Royal Mauian #614
2 bedrooms
2 bathrooms
Sleeps 4
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Wailea Vacation Rentals
Wailea is a great destination if you are looking to relax, unwind, and soak up some sun. With its amazing beaches and luxurious spas, it is a pampering and refreshing vacation that you will never want to return from. Why go back to a simple hotel room when your accommodations can make you continue feeling like royalty even after the activities of the day are done? With a wide variety of vacation rentals, from cozy condos to large beachside villas, you can experience Wailea like one of the locals in your very own rental home no matter what your budget or space needs are.
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Wailea Vacation Rentals
Wailea is a great destination if you are looking to relax, unwind, and soak up some sun. With its amazing beaches and luxurious spas, it is a pampering and refreshing vacation that you will never want to return from. Why go back to a simple hotel room when your accommodations can make you continue feeling like royalty even after the activities of the day are done? With a wide variety of vacation rentals, from cozy condos to large beachside villas, you can experience Wailea like one of the locals in your very own rental home no matter what your budget or space needs are.
A Wailea Vacation
No matter how you like to relax, there is sure to be a great place to do it in Wailea. From an indulgent day at the Spa Grande to tee time at Wailea Old Blue Course, it is full of ways to treat yourself and have a great time. If you're feeling adventurous, Hawaiian Sailing Canoe Adventures allows small groups to enjoy sailing in an outrigger canoe, or if you just want to relax on the beach, Keawakapu is a perfect choice for everything from sunning to snorkeling. Whatever the day's adventures bring, choosing a vacation rental to stay in means you can go back to the privacy and comfort of your very own rental home away from home for a truly authentic experience.
Family-Friendly Wailea
From exploring the beaches to catching a dinner show at Honua'ula Luau, there are a variety of great experiences for children when vacationing to Wailea. With vacation rentals, you can rent a property to accommodate nearly any size family, and it is a fantastic excuse to bring everyone along. Without having to pay for extra hotel rooms, it can also be a great money saver when traveling with a large group. Enjoying a Wailea vacation with the entire family at your very own rental home will be sure to create wonderful memories for years to come.