Wailea: Vacation Rental By Owner

Showing 20 Of 97 Vacation Rentals

Condo Select Dates for Price

1 Bed

2 Baths

(13) Exceptional
Wailea, HI

Highly cleaned and sanitized for your vacation. Ask about out AlohaSafeStay program. NEW! For the First time in rental pool - Gorgeous and spacious ground... ...more
Condo $722 / Nightly

2 Bed

2 Baths

(14)
Wailea, HI

Wailea Elua Village is the premier resort community located directly on Ulua beach in Wailea featuring 24 acres of lush tropical landscapes, luxury accommodations... ...more
Condo $1,555 / Nightly

3 Bed

3 Baths

(10) Excellent
Wailea, HI

Wailea Elua Village is a premier property located on the beach in Wailea featuring 152 condos on 24 acres of lush tropical landscapes. Luxury accommodations and... ...more
Condo $778 / Nightly

2 Bed

2 Baths
Wailea, HI

The world is changing, and we are changing with it. Here at CB Island Vacations, we have taken the time to revamp our practices to ensure a clean and safe... ...more
Villa Select Dates for Price

3 Bed

4 Baths

(17)
Wailea, HI

The world is changing, and we are changing with it. Here at CB Island Vacations, we have taken the time to revamp our practices to ensure a clean and safe... ...more
Condo $314 / Nightly

2 Bed

2 Baths

(15)
Wailea, HI

The world is changing, and we are changing with it. Here at CB Island Vacations, we have taken the time to revamp our practices to ensure a clean and safe... ...more
Condo $700 / Nightly

2 Bed

2 Baths

(22)
Wailea, HI

A modern 2 bedroom, 2 bath condo w. extra bunk beds and an amazing ocean view! South Maui is one of the most beautiful destinations in all of Maui and Wailea... ...more
Condo Select Dates for Price

2 Bed

2 Baths

(37) Excellent
Wailea, HI

Palms at Wailea #205 is a fully remodeled, 2 bedroom / 2 bath unit with a tropical garden view, with a partial ocean view from the lanai and living room. Located... ...more
Condo Select Dates for Price

2 Bed

2 Baths

(53)
Wailea, HI

Palms at Wailea #1503 is one of the best located condos in this property; situated in the inner circle providing views out to Maalaea Bay, West Maui Mountains... ...more
Condo $307 / Nightly

2 Bed

2 Baths

(50)
Wailea, HI

Palms at Wailea #603 has a fully equipped kitchen, washer and dryer and unlike most units at the Palms, it is fully air conditioned. It has flat screen TVs, high... ...more
Condo $353 / Nightly

2 Bed

2 Baths

(52) Excellent
Wailea, HI

Palms at Wailea #1508 is an upstairs ocean view 2 bedroom 2 bath unit with a full kitchen, washer and dryer, fully air conditioned, high speed wireless service.... ...more
Condo $401 / Nightly

1 Bed

2 Baths

(1) Exceptional
Wailea, HI

Palms at Wailea #308 is a 1 bedroom, 2 bath unit on the second floor with split system A/C throughout, a fully equipped kitchen, washer and dryer, 2 flat-screen... ...more
Condo $377 / Nightly

2 Bed

2 Baths

(6) Excellent
Wailea, HI

Palms at Wailea #704 is a 2 bedroom, 2 bath unit on the second floor with a partial ocean view, and split system A/C in both bedrooms and the living. There is a... ...more
Condo $339 / Nightly

1 Bed

1 Baths

(21) Excellent
Wailea, HI

Wailea Ekahi #25-C is a 1 bedroom, 1 bath ground floor condo with room unit air conditioning in both the living room and bedroom, a fully-equipped kitchen, washer... ...more
Condo $354 / Nightly

2 Bed

1 Baths

(47)
Wailea, HI

Leinaala #105 is a 2 bedroom, 1 bath ground floor ocean front unit with an amazing panoramic ocean view. It has a fully-equipped kitchen, a flat-screen TV, DVD... ...more
Condo $346 / Nightly

1 Bed

1 Baths

(12) Wonderful
Wailea, HI

The world is changing, and we are changing with it. Here at CB Island Vacations, we have taken the time to revamp our practices to ensure a clean and safe... ...more
Villa $975 / Nightly

3 Bed

4 Baths

(15)
Wailea, HI

The world is changing, and we are changing with it. Here at CB Island Vacations, we have taken the time to revamp our practices to ensure a clean and safe... ...more
Condo Select Dates for Price

2 Bed

2 Baths

(18)
Wailea, HI

The world is changing, and we are changing with it. Here at CB Island Vacations, we have taken the time to revamp our practices to ensure a clean and safe... ...more
Condo $367 / Nightly

2 Bed

2 Baths

(104)
Wailea, HI

Wailea Grand Champions #48 2 bd, 2 ba ocean view unit. This beautiful 2 bedroom, 2 bath vaulted-ceiling penthouse unit includes 180° expansive ocean views and... ...more
Condo $365 / Nightly

2 Bed

2 Baths

(51) Excellent
Wailea, HI

Wailea Grand Champions #45 is a tastefully remodeled 2 bedroom 2 bath unit on the 3rd floor with an incredible ocean view. Please note that there is no elevator... ...more

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Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Wailea. Many accommodations in Wailea provide "Beach", there are 4, or there are 4 of Vacation Rentals in Wailea with a "Romantic", there are also 4 with "Scuba Diving - Snorkling", which is another great reason to visit Wailea.

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Wailea: Vacation Rental By Owner

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Vacation Rentals by Bedroom size in Wailea

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Popular Rental Amenities in Wailea

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