A coastal landscape with a prominent green hill and a rocky shoreline.

Kahakuloa Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Kahakuloa vacation rentals

A beach with clear turquoise water, sandy shore, palm trees, and a resort building in the background.

1. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,889 reviews)
"Love this place!"
United States
Diana
$224 nightly
The price is $266
Oct 25 - Oct 26
Total with taxes and fees
Napili Shores Maui by OUTRIGGER
A tropical garden with a waterfall, lush greenery, and a gazebo.

2. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,354 reviews)
"Great Stay"
United States
Roopa Rani
$264 nightly
The price is $314
Oct 10 - Oct 11
Total with taxes and fees
Aston Kaanapali Shores
A table with two drinks and a flower on a balcony overlooking the ocean.

3. Kapalua Ridge Villas Resort by KBM

Kapalua Ridge Villas Resort by KBM
4.5 star property
Lahaina
9.6 out of 10, Exceptional, (18 reviews)
"Todo excelente!"
Mexico
Lizbeth
$763 nightly
The price is $906
Oct 17 - Oct 18
Total with taxes and fees
Kapalua Ridge Villas Resort by KBM
A spacious living room with a large window overlooking the ocean, furnished with wicker chairs, a sofa, and a glass coffee table.

4. Aston Mahana at Kaanapali

Aston Mahana at Kaanapali
3.5 star property
Kaanapali
9.0 out of 10, Wonderful, (1,833 reviews)
"Clean nice resort,with beautiful views and reasonable pricing!"
United States
Amit
$272 nightly
The price is $323
Oct 7 - Oct 8
Total with taxes and fees
Aston Mahana at Kaanapali
A resort pool with red umbrellas, palm trees, and a view of the ocean.

5. OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (3,060 reviews)
"We had a great stay at the"
United States
Aprille A
$902 nightly
The price is $980
Oct 26 - Oct 27
Total with taxes and fees
OUTRIGGER Honua Kai Resort & Spa
A beach view with lounge chairs and a clear sky.

6. Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (656 reviews)
"Nice and clean stay! "
United States
Beverly
$281 nightly
The price is $334
Oct 5 - Oct 6
Total with taxes and fees
Napili Sunset on the Beach
A beach with clear blue water, palm trees, and a resort in the background.

7. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (241 reviews)
"thank you for the best stay! perfect location, stunning beach with walking distance to beach, cafe, and rentals. room had everything we needed, recommend upgrading to ocean view it was a treat!"
United States
ASHLEY
$192 nightly
The price is $228
Nov 3 - Nov 4
Total with taxes and fees
Napili Village Hotel
A resort with a pool, palm trees, and a view of the ocean.

8. The Westin Nanea Ocean Villas, Ka'anapali

The Westin Nanea Ocean Villas, Ka'anapali
4.0 star property
Lahaina
9.4 out of 10, Exceptional, (533 reviews)
"It was beautiful hotel and we love to walk to the beach."
United States
Maria
$559 nightly
The price is $664
Oct 19 - Oct 20
Total with taxes and fees
The Westin Nanea Ocean Villas, Ka'anapali
A resort with a pool, palm trees, and a night scene with fire torches.

9. Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
4.0 star property
Kannapali Beach Area
8.6 out of 10, Excellent, (254 reviews)
"Great property very close to everything"
United States
Carroll M
$511 nightly
The price is $607
Oct 18 - Oct 19
Total with taxes and fees
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
A view of a beach with palm trees and a sailboat on the water.

10. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (484 reviews)
"Great place"
United States
Alessio
$561 nightly
The price is $666
Oct 7 - Oct 8
Total with taxes and fees
The Whaler Resort Kaanapali Beach
A room with a large glass door leading to a balcony with a view of the ocean and palm trees.

11. Kapalua Bay Villas Resort by KBM

Kapalua Bay Villas Resort by KBM
5.0 star property
Kapalua
10.0 out of 10, Exceptional, (1 review)
"Service was impeccable, they took care of our every need promptly and gracefully. Beautiful setting."
United States
Mariana
$870 nightly
The price is $1,033
Oct 13 - Oct 14
Total with taxes and fees
Kapalua Bay Villas Resort by KBM
A resort with multiple bungalow-style buildings, a swimming pool, and a beach.

12. Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa
5.0 star property
Lahaina
7.8 out of 10, Good, (27 reviews)
"Place was beautiful and I really enjoyed the live music under the stats every night"
United States
AURA MARINA
$370 nightly
The price is $439
Nov 3 - Nov 4
Total with taxes and fees
Royal Lahaina Bungalows & Spa
A patio with two barbecue grills, a pathway, and a view of the sea and mountains.

13. Kuleana Club - 320

Kuleana Club - 320
2.5 star property
Lahaina
10.0 out of 10, Exceptional, (1 review)
"Quiet and clean! Spent the week with my daughter and had such a wonderful vacation. Located on the west side of Maui, near so many sandy beaches and restaurants. Snorkeled at Black Rock beach and swam with the sea turtles and fish only found in Hawaii . The condo had a full kitchen that we used through-out the stay. We never ran out of things to do. There were sea turtles on the beach on the condo property. Spotted whales and dolphins off the coast from our balcony. We looked forward to...
United States
Scott
Kuleana Club - 320
A swimming pool with a curved design, surrounded by palm trees and lounge chairs, with a building in the background.

14. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,641 reviews)
"The property was a fantastic place to stay. The beach that is in front of the property is excellent for swimming and snorkeling."
United States
Marie
$295 nightly
The price is $351
Nov 1 - Nov 2
Total with taxes and fees
Aston Maui Kaanapali Villas
A tropical garden with a pool, palm trees, and a view of the ocean.

15. Royal Kahana 119 Studio Studio Bedroom Condo by RedAwning

Royal Kahana 119 Studio Studio Bedroom Condo by RedAwning
4.0 star property
Lahaina
8.0 out of 10, Very good, (4 reviews)
"Location was great. Condo was a little dated. Toaster was broken and fridge was on its’ last leg but when we needed anything we called Epic Realty and they got right on it. They were very good. "
United States
Malachy
$871 nightly
The price is $1,034
Oct 6 - Oct 7
Total with taxes and fees
Royal Kahana 119 Studio Studio Bedroom Condo by RedAwning
A coastal residential area with houses, a road, and a view of the ocean.

16. Kapalua Bay Villa 32g4 1 Bedroom Villa by RedAwning

Kapalua Bay Villa 32g4 1 Bedroom Villa by RedAwning
3.5 star property
Lahaina
8.0 out of 10, Very good, (1 review)
$1,214 nightly
The price is $1,441
Oct 11 - Oct 12
Total with taxes and fees
Kapalua Bay Villa 32g4 1 Bedroom Villa by RedAwning
A bathroom with a bathtub and a view of the beach and ocean through a large window.

17. Sands Of Kahana 315 2bd/2ba Oceanfront 2 Bedroom Condo by RedAwning

Sands Of Kahana 315 2bd/2ba Oceanfront 2 Bedroom Condo by RedAwning
3.5 star property
Lahaina
$1,497 nightly
The price is $1,777
Oct 6 - Oct 7
Total with taxes and fees
Sands Of Kahana 315 2bd/2ba Oceanfront 2 Bedroom Condo by RedAwning
A resort with a pool, palm trees, a waterfall, and a view of the ocean.

18. The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas
4.0 star property
Kannapali Beach Area
8.6 out of 10, Excellent, (1,167 reviews)
"The facilities were exactly as described. Our ocean front room and the hotel amenities were wonderful."
Canada
James
$495 nightly
The price is $588
Oct 11 - Oct 12
Total with taxes and fees
The Westin Ka'anapali Ocean Resort Villas
A resort pool area with palm trees, a pool, and a tiki torch.

19. Marriott's Maui Ocean Club - Lahaina & Napili Towers

Marriott's Maui Ocean Club - Lahaina & Napili Towers
4.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (229 reviews)
"Resort has everything you need!"
United States
Jacob
$495 nightly
The price is $588
Oct 23 - Oct 24
Total with taxes and fees
Marriott's Maui Ocean Club - Lahaina & Napili Towers
A resort with multiple-story buildings, a swimming pool, palm trees, and a view of the ocean.

20. Papakea H404 3 Bedroom Condo by RedAwning

Papakea H404 3 Bedroom Condo by RedAwning
4.0 star property
Lahaina
10.0 out of 10, Exceptional, (1 review)
"We had a great stay with two other couples. The unit is well kept as are the grounds. Some good places to eat without having to drive. My only criticism is that none of the lights are very bright except those in the kitchen. We could not play cards at the dinning table because of this. We had to arrange chairs around the kitchen counter."
United States
Ronald
$1,708 nightly
The price is $2,027
Oct 6 - Oct 7
Total with taxes and fees
Papakea H404 3 Bedroom Condo by RedAwning
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.
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Top Kahakuloa Hotel Reviews

Hilton Grand Vacations Club Maui Bay Villas

Hilton Grand Vacations Club Maui Bay Villas

10/10 Excellent
"The rooms are stunning! The pool was beautiful and the kiddos loved it! My only complaint was the second we checked in they pushed a time share hard and the pool drinks were $18 for Crappy piña colada and $16 for a virgin piña colada!"
Jaymee 4-night trip
Posted 12 hours ago
Hilton Grand Vacations Club Maui Bay Villas

Find out more about Kahakuloa

Everything you need to know about Kahakuloa vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kahakuloa vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kahakuloa vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kahakuloa vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kahakuloa. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Kahakuloa in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $228 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Kahakuloa rentals

At Expedia, we put the best Kahakuloa vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Kahakuloa rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kahakuloa vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kahakuloa. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Kahakuloa?

Yes, you can find vacation rentals near well known local attractions in Kahakuloa, or you can choose a more secluded option if you'd like a relaxing place to stay. Kahakuloa is known for its beaches and restaurants. Make sure you have time to check out the sporting events while you're in the area.

What's the top vacation rental that Kahakuloa has to offer?

Yonegan Maui Getaways - Haiku : This vacation home rental outside of Kahakuloa is located near the beach and has a hot tub, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a microwave, a coffee maker, and kitchenware.

What’s there to see and do in Kahakuloa?

Explore the area and family-friendly sights such as Hawaii Nature Center of Iao Valley, or get out into nature at a spot like Kahakuloa Beach. You’ll find favorite places to visit like Kaanapali Beach and Whalers Village in the larger area.

What’s a vacation rental in Kahakuloa like?

A vacation rental is a private property where you can stay for a couple of days or more in Kahakuloa. Vacation rentals offer extras such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a family getaway.