Choose from 3,255 vacation rentals located in Wailea, Hawaii. Top filters in Wailea include Internet / Wifi, Kitchen / Kitchenette, and Pool. Prices range from $85 to $10,185 per night. Our most popular vacation rental types near Wailea are Condo and Hotel.

Top vacation rentals in Wailea

Beach nearby, sun loungers, beach towels
4.9
Outstanding(251 Reviews)
Condo
 in Kihei
Absolutely Incredible Penthouse Front Facing Ocean Views with Pickleball!
2 guests · 1 bath
Pool · Kitchen / Kitchenette · Air conditioner

Condo in Wailea, for $199 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
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Property view
4.7
Outstanding(110 Reviews)
Hotel
 in Wailea
5star
Hotel Wailea, Relais & Châteaux - Adults Only
Garden · Pool · Kitchen / Kitchenette

This Hotel for $372 in Wailea, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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4.1
Excellent(104 Reviews)
Hotel
 in Wailea
3star
Maui Kamaole
Garden · Pool · Kitchen / Kitchenette

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

$$$$
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Beachfront
Property view
4.2
Excellent(77 Reviews)
Resort
 in Wailea
Andaz Maui at Wailea Resort - A Concept by Hyatt
Garden · Pool · Pets allowed

Are you ready to indulge in a relaxing getaway? Our Resort in Wailea has everything you need for a rejuvenating stay. Treat yourself to Andaz Maui at Wailea Resort - A Concept by Hyatt's exceptional amenities, such as Air conditioner, Internet / Wifi and Laundry.

$$$$
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Vacation rentals with internet & wifi in Wailea

Beach nearby, beach umbrellas
5.0
Outstanding(209 Reviews)
Condo
 in Kihei
5-Star Reviews! All Remodeled! Split Air! Quiet Building 5! Ocean/Garden View!
2 guests · 1 bedroom · 2 baths
Pool · Kitchen / 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 $195 for your next trip.

$$$$
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4.3
Excellent(472 Reviews)
Apartment hotel
 in Wailea
Aston Maui Hill
Garden · Pool · Kitchen / Kitchenette

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

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Beachfront
Property view
4.6
Outstanding(160 Reviews)
Resort
 in Wailea
Four Seasons Resort Maui at Wailea
Garden · Pool · Pets allowed

When traveling to Wailea, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $436 per night.

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Beachfront
Property view
3.9
Good(72 Reviews)
Resort
 in Wailea
Mana Kai Maui - Official Onsite Rental Company
Garden · Pool · Kitchen / Kitchenette

Looking to create some memories in Wailea? Look no further than our Resort, Mana Kai Maui - Official Onsite Rental Company. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Smoking allowed, 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 $85-$10,185. The average price for rentals in Wailea is $339 per night.

What are the most popular vacation rental amenities in Wailea?

  • Internet / Wifi
  • Kitchen / Kitchenette
  • Pool

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