Book Villas in Kaupakulua, HI
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Top Villas in Kaupakulua
Panoramic Ocean Views at Wailea Beach Villas I503
Wailea HI
This villa features a gym and a hot tub. Laundry facilities, concierge services, and barbecue grills are also on offer.
Pool
Hot Tub
Gated 2-story beach house with big yard
Kihei HI
This villa features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
5 Star Ocean View, Beach House Chic, Click the Video tour below!
Wailea HI
This villa features an outdoor pool and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
PRIME WHALE SEASON JANUARY 1-8 NOW AVAILABLE!!
Kihei HI
$570 nightly
The price is $667 total per night
$667 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
This villa features an outdoor pool and a hot tub. Laundry facilities and barbecue grills are also provided.
Pool
Hot Tub
I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY
Kihei HI
This villa features an outdoor pool and a gym. There's a hot tub on site, and laundry facilities and concierge services are also offered.
Pool
Hot Tub
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Kihei HI
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
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views
Kula HI
$984 nightly
The price is $1,152 total per night
$1,152 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
This villa features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
Kihei HI
This villa features a gym and a hot tub. Laundry facilities and barbecue grills are also provided.
Pool
Hot Tub
Escape to Ho'olei – Ocean Views & Luxe Comfort
Wailea HI
This villa features a gym and a hot tub. Laundry facilities and barbecue grills are also provided.
Pool
Hot Tub
Exquisite Oceanview Villa with Resort Amenities in Gated Community
Wailea HI
This villa features a gym and a hot tub. Laundry facilities and barbecue grills are also provided.
Pool
Hot Tub
Panoramic Ocean Views! - Luxury Villa! - Owner Direct!
Wailea-Makena HI
This villa features an outdoor pool and a gym. Families will appreciate the arcade/game room and onsite laundry facilities. Enjoy the hot tub and conveniences like a garden and concierge services.
Pool
Hot Tub
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
3900 Wailea Alanui Drive Kihei HI
$795 nightly
The price is $944 total per night from Jan 4 to Jan 5
$944 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.6/10 Exceptional! (999 reviews)
Kaupakulua Villas essential information
Accommodation | 72 Villas |
|---|---|
Lowest Price | $275 |
Highest Price | $1,178 |
Popular accommodation | Panoramic Ocean Views at Wailea Beach Villas I503, Gated 2-story beach house with big yard, 5 Star Ocean View, Beach House Chic, Click the Video tour below!, PRIME WHALE SEASON JANUARY 1-8 NOW AVAILABLE!!, I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY, Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere, Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views, Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!, Escape to Ho'olei – Ocean Views & Luxe Comfort, Exquisite Oceanview Villa with Resort Amenities in Gated Community, Panoramic Ocean Views! - Luxury Villa! - Owner Direct!, Exquisite Spacious Wailea Beach Villas H102 |
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