Compare Olowalu Villas

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Villas in Olowalu

RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS

RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS

Kihei HI
At this villa, guests have access to an outdoor pool, laundry facilities, and a garden. This beach villa also has barbecue grills.
Pool
Kitchen
Oceanfront penthouse w/ private lanai and beach access

Oceanfront penthouse w/ private lanai and beach access

Kihei HI
Guests staying at this villa enjoy a gym, a hot tub, and barbecue grills.
Pool
Hot Tub
Kapalua Bay 29B4 Refined Oceanfront Living with Molokai Views

Kapalua Bay 29B4 Refined Oceanfront Living with Molokai Views

Lahaina HI
$893 nightly
The price is $1,014 total per night
$1,014 total
Aug 9 - Aug 10
Total with taxes and fees
Guests staying at this villa have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere

Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere

Kihei HI
This villa features an outdoor pool, a children's pool, and a gym. Staff members can help with accommodation requests, and provide concierge services. Other amenities at this beach villa include free WiFi in public areas, a hot tub, and laundry facilities.
Pool
Hot Tub
~This is Wailea Living~

~This is Wailea Living~

Kihei HI
Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. This golf villa also has barbecue grills.
Pool
Hot Tub
OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!

OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!

Lahaina HI
$905 nightly
The price is $1,026 total per night
$1,026 total
Aug 10 - Aug 11
Total with taxes and fees
Guests staying at this villa have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Honua Kai Luana Garden Villas 7B - Private Villa, 3BR, Lanai & BBQ, Resort Pools

Honua Kai Luana Garden Villas 7B - Private Villa, 3BR, Lanai & BBQ, Resort Pools

Kaanapali HI
Guests of this villa enjoy features like a gym, a hot tub, and laundry facilities. Additional amenities include barbecue grills and a garden.
Pool
Hot Tub
Stunning Ocean View at Kapalua Bay Villas

Stunning Ocean View at Kapalua Bay Villas

Kapalua HI
At this villa, guests have access to an outdoor pool, laundry facilities, and barbecue grills.
Pool
Kitchen
Honua Kai Ground Floor # Luana 1B - 3 bed / 3 bath villa - front side location

Honua Kai Ground Floor # Luana 1B - 3 bed / 3 bath villa - front side location

Lahaina HI
Guests staying at this villa enjoy an outdoor pool, a gym, and a hot tub. Friendly staff can provide concierge services, and also offer advice about sightseeing. Other amenities at this beach villa include laundry facilities, barbecue grills, and a garden.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Olowalu
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Olowalu

    Aston Kaanapali Shores

    Aston Kaanapali Shores

    3445 Lower Honoapiilani Hwy Lahaina HI
    $264 nightly
    The price is $314 total per night from Aug 13 to Aug 14
    $314 total
    Aug 13 - Aug 14
    Total with taxes and fees
    8.8/10 Excellent! (4,241 reviews)
    Grand Wailea Maui, A Waldorf Astoria Resort

    Grand Wailea Maui, A Waldorf Astoria Resort

    3850 Wailea Alanui Drive Kihei HI
    $786 nightly
    The price is $933 total per night from Aug 22 to Aug 23
    $933 total
    Aug 22 - Aug 23
    Total with taxes and fees
    8.8/10 Excellent! (1,007 reviews)
    Royal Lahaina Resort & Bungalows

    Royal Lahaina Resort & Bungalows

    2780 Kekaa Dr Lahaina HI
    $283 nightly
    The price is $336 total per night from Sep 1 to Sep 2
    $336 total
    Sep 1 - Sep 2
    Total with taxes and fees
    8.6/10 Excellent! (1,791 reviews)

Luxury Villas

Book luxury villas in Olowalu
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Olowalu. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Olowalu, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Olowalu
You won’t have a problem finding your own space in Olowalu. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Olowalu on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Olowalu rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Olowalu Villas essential information

Accommodation
339 Villas
Lowest Price
$314
Highest Price
$1,026
Popular accommodation
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS, Oceanfront penthouse w/ private lanai and beach access, Kapalua Bay 29B4 Refined Oceanfront Living with Molokai Views, Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere, ~This is Wailea Living~, OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!, Honua Kai Luana Garden Villas 7B - Private Villa, 3BR, Lanai & BBQ, Resort Pools, Stunning Ocean View at Kapalua Bay Villas, Honua Kai Ground Floor # Luana 1B - 3 bed / 3 bath villa - front side location