Wailea, HI Vacation Rentals

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 $89 to $10,185 per night. Our most popular vacation rental types near Wailea are Apartment and Hotel.

Top vacation rentals in Wailea

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5.0 / 5.0

Outstanding(216 Ratings)

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 $293 for your next trip.

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Beach nearby, sun loungers, beach towels

4.9 / 5.0

Outstanding(278 Ratings)

Absolutely Incredible Penthouse Front Facing Ocean Views !

Apartment

in Kihei

2 guests · 1 bath

Pool · Kitchen or Kitchenette · Air conditioner

Apartment in Wailea, for $298 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 / 5.0

Outstanding(127 Ratings)

Hotel Wailea, Relais & Châteaux - Adults Only

Hotel

in Wailea

5star

1 king bed

Garden · Pool · Kitchen or Kitchenette

This Hotel for $385 in Wailea, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

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Beachfront

4.3 / 5.0

Excellent(261 Ratings)

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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Campground/ RV Resort

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Explore vacation rentals with the most popular amenities in Wailea

Vacation rentals with a kitchen in Wailea

On the beach, sun loungers, beach towels

5.0 / 5.0

Outstanding(190 Ratings)

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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5.0 / 5.0

Outstanding(181 Ratings)

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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4.1 / 5.0

Excellent(108 Ratings)

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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4.2 / 5.0

Excellent(8 Ratings)

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.