Choose from 3,539 vacation rentals located in Wailea, Hawaii. Top filters in Wailea include Kitchen or Kitchenette, Internet / Wifi, and Pool. Prices range from $135 to $15,465 per night. Our most popular vacation rental types near Wailea are Apartment and Hotel.

Top vacation rentals in Wailea

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Beach nearby
5.0
Outstanding(216 Reviews)
5-Star Reviews! All Remodeled! Split Air! Quiet Building 5! Ocean/Garden View!
Apartment
 in Kihei
2 guests · 1 bedroom · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Wailea at 5-Star Reviews! All Remodeled! Split Air! Quiet Building 5! Ocean/Garden View! for $445 for your next trip.

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Beach nearby, sun loungers, beach towels
4.9
Outstanding(278 Reviews)
Absolutely Incredible Penthouse Front Facing Ocean Views !
Apartment
 in Kihei
2 guests · 1 bath
Pool · Kitchen or Kitchenette · Air conditioner

Apartment in Wailea, for $452 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

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Bird's eye view, Pool view, Sea view, Swimming pool
4.7
Outstanding(127 Reviews)
Hotel Wailea, Relais & Châteaux - Adults Only
Hotel
 in Wailea
5star
1 king bed
Garden · Pool · Kitchen or Kitchenette

This Hotel for $585 in Wailea, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

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Beachfront
Other
4.3
Excellent(261 Reviews)
Wailea Beach Resort - Marriott, Maui
Resort
 in Wailea
1 king bed
Garden · Pool · Kitchen or Kitchenette

Discover the beauty of Wailea with a stay at Wailea Beach Resort - Marriott, Maui, a top rated Resort with amenities such as Air conditioner, Fireplace and Internet / Wifi, and more.

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Vacation rentals with a kitchen in Wailea

On the beach, sun loungers, beach towels
5.0
Outstanding(190 Reviews)
FULL OCEAN VIEW CLEAN SPACIOUS HIGH END REMODELED A/C IN LIVING + BEDROOMS
Apartment
 in Kihei
5 guests · 3 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette

Indulge in a peaceful retreat at FULL OCEAN VIEW CLEAN SPACIOUS HIGH END REMODELED A/C IN LIVING + BEDROOMS , our elegant Apartment in Wailea. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

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On the beach, beach towels
5.0
Outstanding(181 Reviews)
Wow! Best Rated VRBO condo in Mana Kai Maui Resort, Luxury at Ocean End, 4th Flr
Apartment
 in Kihei
4 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette

Discover the beauty of Wailea with a stay at Wow! Best Rated VRBO condo in Mana Kai Maui Resort, Luxury at Ocean End, 4th Flr, a top rated Apartment with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

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Property view
4.1
Excellent(108 Reviews)
Maui Kamaole
Apartment
 in Wailea
Garden · Pool · Kitchen or Kitchenette

Looking to create some memories in Wailea? Look no further than our Apartment, Maui Kamaole. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

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Property building, On site
4.2
Excellent(8 Reviews)
Makena Surf- CoralTree Residence Collection
Apartment hotel
 in Wailea
1 king bed, 1 sofa bed, 2 single beds
Garden · Pool · Kitchen or Kitchenette
Most favorited

Indulge in a peaceful retreat at Makena Surf- CoralTree Residence Collection, our elegant Apartment hotel in Wailea. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

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Wailea

Wailea travel guide

Let us help you plan your perfect Wailea vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Wailea, and more.

Frequently asked questions

What is the price range for rentals in Wailea?

Vacation rentals in Wailea have a price range between $135-$15,465. The average price for rentals in Wailea is $482 per night.

What are the most popular vacation rental amenities in Wailea?

  • Kitchen or Kitchenette
  • Internet / Wifi
  • Pool

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