Search Villas in Kaupakulua

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

Compare 78 Villas in Kaupakulua with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (164)
"Peaceful unobstructed view of Haleakala Lanai and Moloka’i beyond Kahalawai"
The price is SAR 1,688
SAR 3,738 total
includes taxes & fees
6 May - 7 May
Mar- May special rates. Eco friendly modern home, gorgeous Ocean & Mt views
~ This Is Wailea Living ~
Point of interest

~ This Is Wailea Living ~

10.0 out of 10, Exceptional, (121)
"Great location. Everything just as advertised"
~ This Is Wailea Living ~
Hula On In to Beach House Chic Style, Click the Video tour below!
Outdoor pool

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

10.0 out of 10, Exceptional, (130)
"Condo was very clean, comfortable, and just perfect for our week vacation in Maui with our teen children. Would highly recommend! "
Hula On In to Beach House Chic Style, Click the Video tour below!
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Outdoor pool, an infinity pool

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

10.0 out of 10, Exceptional, (74)
"Great property and location. Would come back and rent anytime."
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Private Ocean Front at Wailea Beach Villas B102
Pool

Private Ocean Front at Wailea Beach Villas B102

10.0 out of 10, Exceptional, (26)
"The unit and property were beautiful. Very spacious and loved being so close to the ocean. Hope to be back again soon. "
Private Ocean Front at Wailea Beach Villas B102
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
Pool

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

10.0 out of 10, Exceptional, (53)
"Property is totally amazing. Wonderful location, amenities and cleanliness. Our family loved our stay. We will return. "
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
Exquisite Oceanview Villa with Resort Amenities in Gated Community
Pool

Exquisite Oceanview Villa with Resort Amenities in Gated Community

10.0 out of 10, Exceptional, (62)
"As advertised, property was lovely and suitable for our family. Beautiful view and very comfortable. "
Exquisite Oceanview Villa with Resort Amenities in Gated Community
Gated 2-story beach house with big yard
Exterior detail

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (53)
"Had a great time at this place. Tammy was nice and welcoming the place is great. A 1 minute walk to Charlie Young beach. The place is very convenient and well set up for a large group. "
Gated 2-story beach house with big yard
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS
Exterior

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

10.0 out of 10, Exceptional, (187)
"This place is just as advertised. We were a family group of 12 people and had a great time. Highly recommend."
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
A waterfall pool

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

9.6 out of 10, Exceptional, (55)
"We had a wonderful vacation and this location was perfect. After visiting multiple areas in Maui, we decided we like this area best "
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
Honeymooner's Delight, Private Pool & Property,Ocean Views, close to beach.
Outdoor pool

Honeymooner's Delight, Private Pool & Property,Ocean Views, close to beach.

9.8 out of 10, Exceptional, (56)
"We are happy to verify all of Teri’s descriptions as well as previous visitors' comments. ."
Honeymooner's Delight, Private Pool & Property,Ocean Views, close to beach.
5 Star Ocean View, Beach House Chic, Click the Video tour below!
Outdoor pool

5 Star Ocean View, Beach House Chic, Click the Video tour below!

10.0 out of 10, Exceptional, (86)
"Great host had a lovely time thank you so much!"
5 Star Ocean View, Beach House Chic, Click the Video tour below!
Spectacular 3rd Row Villa at Ho'olei with Ocean Views
Pool

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

10.0 out of 10, Exceptional, (56)
"Wonderful time"
Spectacular 3rd Row Villa at Ho'olei with Ocean Views
Exquisite Spacious Wailea Beach Villas H102
Pool

Exquisite Spacious Wailea Beach Villas H102

9.8 out of 10, Exceptional, (64)
"We had a great time staying here. The place had plenty of room and great amenities. Very family friendly and still had quiet places for adults only."
Exquisite Spacious Wailea Beach Villas H102
Villas By The Cove, Villa 3 · Step to White-Sand Beach
Terrace/patio

Villas By The Cove, Villa 3 · Step to White-Sand Beach

9.8 out of 10, Exceptional, (78)
"Wonderful stay."
The price is SAR 1,230
SAR 2,400 total
includes taxes & fees
14 May - 15 May
Villas By The Cove, Villa 3 · Step to White-Sand Beach
Oceanview Penthouse, sleeps up to 16 guests!
Beach nearby

Oceanview Penthouse, sleeps up to 16 guests!

9.4 out of 10, Exceptional, (15)
"Great place, a perfect destination for a family trip"
Oceanview Penthouse, sleeps up to 16 guests!
I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY
Outdoor pool, a heated pool

I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY

10.0 out of 10, Exceptional, (26)
"It was a great stay and the host was very responsive with any questions we may have had. Aloha and mahalo"
I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY
Aloha Villas Resort | 12 Bed, 12.5 Bath
Outdoor dining

Aloha Villas Resort | 12 Bed, 12.5 Bath

9.8 out of 10, Exceptional, (43)
"No detail, communication or service was less than spectacular. From the fully equipped villas to games and lush greenery, we enjoyed our home in paradise for two weeks. Thank you to Jude and Mary for promptly responding to our needs throughout our stay."
Aloha Villas Resort | 12 Bed, 12.5 Bath
CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!
Beach nearby, sun loungers, beach towels

CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!

9.6 out of 10, Exceptional, (64)
"Nice unit. We enjoyed our stay and hope to come back someday soon. The unit was in a quiet area near everything Maui has to offer. The complex was quiet and clean. We would stay again. "
CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!
Rare Find! Ocean and Beach Front Cottage!
On the beach

Rare Find! Ocean and Beach Front Cottage!

Rare Find! Ocean and Beach Front Cottage!
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.
Don't see what you're looking for?
See all available properties in Kaupakulua
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Kaupakulua

Maui Beach Vacation Club
Suite, 2 Bedrooms | Living area | TV

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very Good, (740)
"Great for family"
Maui Beach Vacation Club
Wailea Ekahi - CoralTree Residence Collection
Exterior

Wailea Ekahi - CoralTree Residence Collection

3.0 star property
9.2 out of 10, Wonderful, (533)
"Beautiful property and beach is easily accessed from resort. "
Wailea Ekahi - CoralTree Residence Collection
Sugar Beach Resort
Outdoor pool

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1057)
"We love the location to go anywhere on the island or just a short drive into Kihei. Beautiful beach and nice pool area!"
Sugar Beach Resort
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.

Frequently asked questions

Why book your villa in Kaupakulua with Expedia?
We think arranging a vacation shouldn’t be difficult, so if you’re on the lookout for villas at a nice price, Expedia has your back. Stick to the budget and opt for an all-inclusive stay, or splurge on a luxe villa to spoil your nearest and dearest. Our handy filters make it simple to find a place in Kaupakulua that you’ll adore.
How can I find cheap villas in Kaupakulua?
The easiest way to compare cheap villas in Kaupakulua is with Expedia’s useful filter tool. Fine-tune your search results by amenities, star rating and budget to nab unbeatable deals in just a few clicks.