Embark on a journey of relaxation and adventure in Wailea, Hawaii, where our selection of vacation houses are more than just a place to stay. They are your gateway to exploring the culture, natural beauty, and spirit of the region, ensuring your trip is filled with moments to treasure.

Looking for the perfect vacation home for your group? Whether you want a pet-friendly family escape, a vacation home in the center of Wailea or a cosy couple retreat on the outskirts of town, our selection of vacation homes in Wailea have it all.

Discover a diverse range of vacation houses in Wailea, perfect for any travel style or budget. From quaint cottages to grand villas, our selection spans serene hideaways to rentals in the heart of the city. Your dream stay is just around the corner.

Top Amenities: Kitchen or Kitchenette, Internet / Wifi, Pool, Parking and Laundry

Points of Interest: Haleakalā National Park, Nakalele Blowhole, Waiʻānapanapa State Park, Sea Maui and Molokini Crater

Embark on your Wailea adventure today! Secure your house now and start crafting memorable moments in Hawaii.

Top houses in Wailea

Beachfront
Property view
4.5
Excellent(11 Reviews)
Wailea Sunset Condo - Ekolu #607
House
 in Wailea
Garden · Pool · Pets allowed

This House in Wailea, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Property view
Haleakala Shores A-301, Panoramic Views, Split AC
House
 in Wailea
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

When traveling to Wailea, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $282 per night.

$$$$
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Property view
Hale Kamaole 150, Beautiful Renovation, Split AC
House
 in Wailea
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

This House for $282 in Wailea, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Other
3.4
Average(9 Reviews)
4-309 Kamaole Sands**Newly Remodeled** Steps to Kamaole 3 Beach!
House
 in Wailea
Pool · Kitchen or Kitchenette · Air conditioner

This attractive House in Wailea, $282 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Other
3.6
Good(4 Reviews)
Hale Kamaole
House
 in Wailea
Pool · Kitchen or Kitchenette · Air conditioner

Looking for a memorable stay in Wailea? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

$$$$
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Property view
Kamaole Sands 3-406, Gourmet Kitchen, Split AC
House
 in Wailea
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

When traveling to Wailea, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $282 per night.

$$$$
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Exterior
4.5
Excellent(2 Reviews)
Wonderful Wailea Condo Lanai Water Views
House
 in Kihei
Pool · Kitchen or Kitchenette · Air conditioner

This House in Wailea, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Outdoor pool
5.0
Outstanding(177 Reviews)
Wailea Custom Home, Pool, Panoramic Ocean View, Waterfalls - Maui Ocean Palms
House
 in Kihei
4 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette

Looking for a memorable stay in Wailea? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

$$$$
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Exterior
4.5
Excellent(2 Reviews)
Wonderful Wailea Condo Lanai Water Views
House
 in Kihei
2 guests
Pool · Kitchen or Kitchenette · Air conditioner

Looking for a House in Wailea, this House for $445 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

$$$$
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Pool
Ho'olei Ocean View by Coldwell Banker Island Vacations
House
 in Kihei
2 guests · 3 bedrooms · 1 bath
Pool · Kitchen or Kitchenette · Internet / Wifi

This House for $1,544 in Wailea, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Other
4.5
Excellent(11 Reviews)
126 Hale Kamaole
House
 in Wailea
Pool · Kitchen or Kitchenette · Air conditioner

Nestled in Wailea, this House is perfect for your next vacation. Enjoy 126 Hale Kamaole's top-rated amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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House, 4 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster
Maui Dolphin House 4 Bedroom Home
House
 in Kihei
2 guests
Garden · Pool · Kitchen or Kitchenette

Are you ready to indulge in a relaxing getaway? Our House in Wailea has everything you need for a rejuvenating stay. Treat yourself to Maui Dolphin House 4 Bedroom Home's exceptional amenities, such as Internet / Wifi, Laundry and Balcony or Patio.

$$$$
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Houses with a kitchen in Wailea

Beachfront
Property view
Mana Kai 410 - Ocean front at Keawakapu Beach, AC
House
 in Wailea
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Experience the best of Wailea with this House available for $282. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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View (from property/room)
4.7
Outstanding(4 Reviews)
Stunning ocean view! 2-2 in the heart of Wailea
House
 in Wailea
Garden · Pool · Kitchen or Kitchenette

Looking to create some memories in Wailea? Look no further than our House, Stunning ocean view! 2-2 in the heart of Wailea. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property view
5.0
Outstanding(1 Review)
Kamaole Sands 2-204 - Ocean View Condo, AC, Wi-Fi
House
 in Wailea
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

This attractive House in Wailea, $282 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Swimming pool
3.8
GoodNo Reviews
Grand Champions 144
House
 in Wailea
Pool · Kitchen or Kitchenette · Air conditioner

Experience vacation in Wailea with our House, Grand Champions 144. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property view
Maui Parkshore 410 - Stunning Ocean Views
House
 in Wailea
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Looking for a memorable stay in Wailea? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Internet / Wifi and Balcony or Patio, and more during your stay.

$$$$
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Property view
5.0
OutstandingNo Reviews
Kamaole Sands 5-303, Contemporary Reno, Ocean View
House
 in Wailea
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Experience the best of Wailea with this House available for $282. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property view
Kamaole Sands 3-308, Renovated, Large Lanai, AC
House
 in Wailea
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Discover the beauty of Wailea with a stay at Kamaole Sands 3-308, Renovated, Large Lanai, AC, a top rated House with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property view
Kihei Akahi C-411 - Modern Renovation, Split AC
House
 in Wailea
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Enjoy the best of Wailea in our House, Kihei Akahi C-411 - Modern Renovation, Split AC. A stunning property with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property view
Wailea Ekolu 310 - Panoramic Ocean Views, Split AC
House
 in Wailea
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Soak up the beauty of Wailea in our House, Wailea Ekolu 310 - Panoramic Ocean Views, Split AC. With a range of amenities such as Air conditioner, Dishwasher and Internet / Wifi, you'll feel right at home.

$$$$
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Property view
Kamaole Sands 9-301 - Luxury Renovation, Split AC
House
 in Wailea
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Looking to create some memories in Wailea? Look no further than our House, Kamaole Sands 9-301 - Luxury Renovation, Split AC. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property view
Kamaole Sands 10-403, Split AC, Ocean Views, 2/2
House
 in Wailea
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

This House in Wailea, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Property view
Maui Hill 116, Renovated, Ocean Views, Split AC
House
 in Wailea
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Wailea, at $282 per night for your next great vacation.

$$$$
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