Book Villas in Kaupakulua, HI

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Top Villas in Kaupakulua

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

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

Get rates
This villa features an outdoor pool and a gym. Enjoy the hot tub and perks like free WiFi. Laundry facilities, concierge services, and barbecue grills are also on offer.
Pool
Hot Tub
Gated 2-story beach house with big yard

Gated 2-story beach house with big yard

Get rates
This villa features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Mar- May special rates. Eco friendly modern home, gorgeous Ocean & Mt views

Mar- May special rates. Eco friendly modern home, gorgeous Ocean & Mt views

$1,068 nightly
The price is $1,242 total per night
$1,242 total
Jun 15 - Jun 16
Total includes taxes and fees
This villa features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
~ This Is Wailea Living ~

~ This Is Wailea Living ~

$537 nightly
The price is $625 total per night
$625 total
Jun 3 - Jun 4
Total includes taxes and fees
This villa features an outdoor pool and a hot tub. Laundry facilities and barbecue grills are also provided.
Pool
Hot Tub
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei

Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei

Get rates
This villa features a gym and a hot tub. Laundry facilities and barbecue grills are also provided.
Pool
Hot Tub
Rare Find! Ocean and Beach Front Cottage!

Rare Find! Ocean and Beach Front Cottage!

Get rates
This villa featured laundry facilities and barbecue grills.
Kitchen
Washer
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS

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

Get rates
An outdoor pool is featured at this villa, along with a garden and laundry facilities. Families will appreciate the playground and barbecue grills.
Pool
Kitchen
Hula On In to Beach House Chic Style, Click the Video tour below!

Hula On In to Beach House Chic Style, Click the Video tour below!

Get rates
This villa features an outdoor pool and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!

Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!

Get rates
This villa features a gym and a hot tub. Laundry facilities and barbecue grills are also provided.
Pool
Hot Tub
Spectacular 3rd Row Villa at Ho'olei with Ocean Views

Spectacular 3rd Row Villa at Ho'olei with Ocean Views

Get rates
This villa features a hot tub and a sauna. A garden, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
Wailea Beach Villas M312: Your Hawaiian Paradise

Wailea Beach Villas M312: Your Hawaiian Paradise

Get rates
This villa features a gym and a hot tub. Laundry facilities, concierge services, and barbecue grills are also on offer.
Hot Tub
Kitchen
Panoramic Ocean Views at Wailea Beach Villas I503

Panoramic Ocean Views at Wailea Beach Villas I503

Get rates
This villa features a gym and a hot tub. Laundry facilities, concierge services, and barbecue grills are also on offer.
Hot Tub
Kitchen
Don't see what you're looking for?
See all available properties in Kaupakulua
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.

Top hotels in Kaupakulua

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive, Kihei, HI
$795 nightly
The price is $938 total per night from Jun 21 to Jun 22
$938 total
Jun 21 - Jun 22
Total includes taxes and fees
9.6/10 Exceptional! (1,000 reviews)

Kaupakulua Villas essential information

Accommodation
79 Villas
Lowest Price
$293
Highest Price
$1,242
Popular accommodation
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere, Gated 2-story beach house with big yard, Mar- May special rates. Eco friendly modern home, gorgeous Ocean & Mt views, ~ This Is Wailea Living ~, Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei, Rare Find! Ocean and Beach Front Cottage!, RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS, Hula On In to Beach House Chic Style, Click the Video tour below!, Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!, Spectacular 3rd Row Villa at Ho'olei with Ocean Views, Wailea Beach Villas M312: Your Hawaiian Paradise, Panoramic Ocean Views at Wailea Beach Villas I503

Explore more Villas

Popular accommodation searches

More places to stay in Kaupakulua