Wailea Vacation Rentals - HolidayHomes base64Hash Wailea Vacation Rentals - HolidayHomes

Wailea Vacation Rentals

Browse 6,782 available vacation homes and compared across 28 trusted partners

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Top-Rated Vacation rentals in Wailea

Book the highest-rated Wailea vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

We use AI to generate the short summary in each offer below, check full description before booking.
Condo Wailea

Property is steps to the beach. Walk to dining and shops. Ground floor.

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Condo Wailea

Condo with private pool, hot tub & grill

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Condo Wailea

Maui Hill 116 - Stunning Renovation - Split AC - 3bd/3ba - Expansive Ocean Views

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House Wailea

PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING

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Condo Wailea

Family-oriented condo with hot tub, BBQ & pool | Water view | Next to the beach

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House Wailea

Vacation home with garden, terrace & grill | Suitable for remote work

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Condo Wailea

Condo with barbeque, pool & hot tub

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Condo Wailea

Condo with heated pool & jacuzzi

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Condo Wailea

Condo with yard, hot tub & heated pool | City view

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Condo Wailea

Direct Ocean Front Property - Mile Long SANDY BEACH - Wailea Ekahi - 1 Bed/2Bth

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Condo Wailea

Family-oriented condo with patio, pool & yard | Next to the beach

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Villa Wailea

Villa with terrace, BBQ & hot tub | Mountain view | Good for workation

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Condo Wailea

Condo with pool, hot tub & BBQ

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House Wailea

Spectacular Panoramic Ocean Views - Private Ohana - Wailea Custom Pole Home

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Condo Wailea

Spacious luxury, ocean view, 2bd high end touches

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Top 15 most Recommended Vacation Rentals in Wailea

Discover your ideal Wailea vacation rental with real-time comparisons of 6,782 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

We use AI to generate the short summary in each offer below, check full description before booking.
House Wailea
House ∙ 15 guests ∙ 5 bedrooms

Wonderful vacation home with barbeque & private pool | Good for workation | Pets are welcome

Wailea, Wailea-Makena, Hawaii, United States
This spacious house rental in Wailea accommodates 15 guests and features a private pool for relaxation and enjoyment.
from $345
per night
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Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with terrace, BBQ & pool | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo accommodates 6 and features a balcony with stunning views, perfect for enjoying the tropical breeze.
from $641
per night
(11)
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Villa Wailea
Villa ∙ 6 guests ∙ 3 bedrooms

Fully equipped villa with sauna, pool & hot tub | Next to the beach

Wailea, Wailea-Makena, Hawaii, United States
This spacious villa in Wailea accommodates 6 guests and features a luxurious pool for ultimate relaxation.
from $1,271
per night
(41)
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Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Fully equipped beautiful condo with heated pool, hot tub & barbecue | Nature view | Next to the beach

Wailea, Wailea-Makena, Hawaii, United States
This 6-person condo in Wailea-Makena features a heated pool and offers a luxurious retreat in a prime location.
from $239
per night
(34)
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Condo Wailea
Condo ∙ 4 guests ∙ 1 bedroom

Condo with pool, BBQ & patio | Good for workation

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo accommodates 4 guests and features a pool for relaxation and enjoyment.
from $192
per night
(69)
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House Wailea
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with patio, barbecue & pool | Water view | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
This spacious house rental in Wailea accommodates 8 guests and features a beautiful pool for relaxation and fun.
from $446
per night
(1)
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Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

Children-friendly condo with pool, jacuzzi & BBQ | Water view

Wailea, Wailea-Makena, Hawaii, United States
This spacious 8-person condo in Wailea features a stunning sea view and offers convenient beach access for a perfect getaway.
from $691
per night
(185)
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Condo Wailea
Condo ∙ 4 guests ∙ 1 bedroom

Fully equipped condo with grill, patio & pool | Next to the beach

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo for 4 features a beautiful balcony overlooking the stunning landscape.
from $295
per night
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House Wailea
House ∙ 10 guests ∙ 4 bedrooms

Child-friendly spacious house with terrace, private pool & hot tub | Nature view | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
This spacious house rental in Wailea accommodates 10 guests and features a private pool for a luxurious getaway.
from $1,281
per night
(109)
View deal

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