Search Villas in Kaupakulua

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

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

Gated 2-story beach house with big yard
Exterior detail

Gated 2-story beach house with big yard

10.0 out of 10, Exceptional, (47)
"Ideal location for beach and ocean lovers! Beach is only 2 minutes away. 30 minutes to other Maui destinations like Lahaina and Road to Hana.Home was beautifully decorated and nice layout. Two twin beds upstairs have a low ceiling so tall people may feel tight. Our family would definitely return to this home rental."
Gated 2-story beach house with big yard
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, (129)
"We loved the condo! Really cleaning well organized. Great space, location and amenities. It has everything you need for a great get away. Groceries, restaurants and beautiful all within 5 min. Thank you for your home away from home."
Hula On In to Beach House Chic Style, Click the Video tour below!
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, (161)
"Secluded and private with a wonderful view and with everything one could ask for to feel at home Upcountry. The owner was very helpful whenever needed. Thanks for the great stay! Looking forward to our return."
The price is SAR 1,969
SAR 4,114 total
includes taxes & fees
5 Apr - 6 Apr
Mar- May special rates. Eco friendly modern home, gorgeous Ocean & Mt views
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, (71)
"Everything was wonderful… thank you so much Linda."
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102
Pool

EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102

10.0 out of 10, Exceptional, (25)
"Positive"
EXCEPTIONAL, PRIVATE, DIRECT OCEAN FRONT VILLA! Wailea Beach Villa B102
~ This Is Wailea Living ~
Point of interest

~ This Is Wailea Living ~

10.0 out of 10, Exceptional, (119)
"I stayed here 2/28-3/7. The pictures did not do this place justice. It was very pretty & lots of space. No problems finding the condo or getting in the unit. There was 2 Shower heads in the HUGE master bathroom. I didn’t expect beach towels, chairs, & all the kitchen & bathroom supplies that were provided! Wow! The area is very quiet. The location is perfect. Only a 10 minute walk to the Wailea shops, restaurants & beach. It is uphill coming back. I had to stop & take a quick break bc of my...
~ This Is Wailea Living ~
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, (185)
"Perfect in every way! The house is well stocked with everything needed. Keith even bought a football and soccer ball after we asked if there was one, how incredibly thoughtful. The location on the beach was great for ending the day with a sunset. "
RARE, GATED, PRIVATE BEACHFRONT HOME! PRIVATE POOL, 6 BEDS 6 BATHS
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)
"My family and I planned this trip back in March 2024 and reserved this property in Ho'olei.Right from the initial reservation process and first payment installment, the interaction with Matthew was excellent and seamless. Matthew was responsive and very helpful.The unit at Ho'olei was remarkable, well located within the property, and most importantly, was extremely clean when we checked in. There was a small welcome gift which was appreciative. The unit was very well equipped with all we needed,...
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
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)
"Great stay at Tamara's condo. The location is fantastic, walking distance to the beach, shops, restaurants and the Wailea beach trail. The condo was well equipped. We easily cooked meals in the kitchen, which had everything we needed. The condo was clean and welcoming. We brought the provided beach chairs and beach towels, to Big Beach. The bathroom had sunscreen and a first aid kit, The band aids came in handy. Having a laundry allowed us to pack light. We really appreciated that Tamara left...
CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!
Luxurious Ocean View Villa at Ho'olei! Experience Hoolei 17-3
Pool

Luxurious Ocean View Villa at Ho'olei! Experience Hoolei 17-3

10.0 out of 10, Exceptional, (62)
"Property is greatView great "
Luxurious Ocean View Villa at Ho'olei! Experience Hoolei 17-3
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, (52)
"Loved this property and the service by Maui Vacations. Perfect stay. Only complain is that there were no Kleenex. Could have called but plenty of toilet paper. "
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
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, (85)
"While I would love to keep this property my little secret, that wouldn’t be fair. Absolutely excellent property, quality, cleanliness, communication and location. Wonderfully supplied kitchen and activities items. WiFi great, TV selections very good. I would select this property everytime. Owners were super friendly and communicative. Thank you!!"
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, (54)
"We had an amazing time. Will be coming back again! "
Spectacular 3rd Row Villa at Ho'olei with Ocean Views
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, (77)
"I enjoyed my stay at the villa! It was very clean, perfectly located, and had everything one could wish for. The pool was also beautiful. I would love to come back!"
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, (14)
"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)
"This property was exactly as described and complete perfection as it related to housing all of our family members. The grounds are beautiful. The pool is gorgeous. The location for us was exactly where we wanted to be and just across the street from the beach. We did have some street noise coming from behind the patio but it wasn't terribly intrusive. The kitchen was well stocked with dishes and utensils as well as small appliances. The Furnishings are modern which included a fair amount of...
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
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, (55)
"Absolutely stunning property. Private pool, love birds and other birds galore. Property is as listed. Watch the whales from the pool deck. We hung out at the pool all the time. Totally private. Terri was wonderful to work with. She kept in touch during our stay. She also stocked our suite with bananas, mango and other treats. The outside shower is to die for. "
Honeymooner's Delight, Private Pool & Property,Ocean Views, close to beach.
Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-4
Pool

Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-4

9.6 out of 10, Exceptional, (69)
"We loved this. The only complain is that we did not get information for check-in three days before. We called your help number and we did get some of the check-in. Had to wait until 4pm exactly to get final codes and it did not work. Reminded me of the Nick Sabin commercial. "
Beautifully Designed Villa! Steps From the Pool! Ho'olei 12-4
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

Wailea Ekahi - CoralTree Residence Collection
Exterior

Wailea Ekahi - CoralTree Residence Collection

3.0 star property
9.2 out of 10, Wonderful, (515)
"Nice comfortable condo on attractive property. "
Wailea Ekahi - CoralTree Residence Collection
Sugar Beach Resort
Outdoor pool

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1046)
"The view was beautiful from the balcony as it was right on the beach. Unit was very clean and had everything you needed for an enjoyable vacation. The king bed was comfortable and it is always nice to have a washer & dryer. The one recommendation I would make would be to upgrade the living room furniture as it is very uncomfortable and outdated. "
Sugar Beach Resort
Wailea Grand Champions - CoralTree Residence Collection
2 outdoor pools

Wailea Grand Champions - CoralTree Residence Collection

3.0 star property
9.0 out of 10, Wonderful, (697)
"location and view from patio was exceptional. cleanliness and appointments in residence were very good. I would recommend this property to everyone."
Wailea Grand Champions - CoralTree Residence Collection
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.