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

Kahakuloa Vacation Rentals

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Our top choices for Kahakuloa vacation rentals

1. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,891 reviews)
"Great property"
United States
Shawn
The price is CA $298
CA $354 total
includes taxes & fees
Oct 25 - Oct 26
Napili Shores Maui by OUTRIGGER

2. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,357 reviews)
"Great Stay"
United States
Roopa Rani
The price is CA $341
CA $447 total
includes taxes & fees
Oct 11 - Oct 12
Aston Kaanapali Shores

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
The price is CA $509
CA $1,303 total
includes taxes & fees
Oct 17 - Oct 18
Kapalua Ridge Villas Resort by KBM

4. Aston Mahana at Kaanapali

Aston Mahana at Kaanapali
3.5 star property
Kaanapali
9.0 out of 10, Wonderful, (1,836 reviews)
"Clean nice resort,with beautiful views and reasonable pricing!"
United States
Amit
The price is CA $352
CA $461 total
includes taxes & fees
Oct 7 - Oct 8
Aston Mahana at Kaanapali

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
The price is CA $537
CA $1,397 total
includes taxes & fees
Oct 26 - Oct 27
OUTRIGGER Honua Kai Resort & Spa

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
The price is CA $427
CA $507 total
includes taxes & fees
Nov 3 - Nov 4
Napili Sunset on the Beach

7. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (242 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
The price is CA $247
CA $293 total
includes taxes & fees
Nov 1 - Nov 2
Napili Village Hotel

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
The price is CA $797
CA $946 total
includes taxes & fees
Oct 30 - Oct 31
The Westin Nanea Ocean Villas, Ka'anapali

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, (255 reviews)
"The suite is awesome!!!!"
United States
Bradford
The price is CA $728
CA $864 total
includes taxes & fees
Oct 21 - Oct 22
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

10. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (486 reviews)
"Great place"
United States
Alessio
The price is CA $350
CA $936 total
includes taxes & fees
Oct 7 - Oct 8
The Whaler Resort Kaanapali Beach

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
The price is CA $524
CA $1,320 total
includes taxes & fees
Oct 13 - Oct 14
Kapalua Bay Villas Resort by KBM

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
The price is CA $463
CA $626 total
includes taxes & fees
Nov 3 - Nov 4
Royal Lahaina Bungalows & Spa

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

14. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,644 reviews)
"Great place will stay again!"
United States
Joseph
The price is CA $314
CA $500 total
includes taxes & fees
Nov 2 - Nov 3
Aston Maui Kaanapali Villas

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
The price is CA $206
CA $1,473 total
includes taxes & fees
Oct 7 - Oct 8
Royal Kahana 119 Studio Studio Bedroom Condo by RedAwning

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)
The price is CA $628
CA $2,053 total
includes taxes & fees
Oct 11 - Oct 12
Kapalua Bay Villa 32g4 1 Bedroom Villa by RedAwning

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
The price is CA $675
CA $2,533 total
includes taxes & fees
Oct 7 - Oct 8
Sands Of Kahana 315 2bd/2ba Oceanfront 2 Bedroom Condo by RedAwning

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
The price is CA $705
CA $837 total
includes taxes & fees
Oct 12 - Oct 13
The Westin Ka'anapali Ocean Resort Villas

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
The price is CA $705
CA $837 total
includes taxes & fees
Oct 28 - Oct 29
Marriott's Maui Ocean Club - Lahaina & Napili Towers

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
The price is CA $585
CA $2,889 total
includes taxes & fees
Oct 7 - Oct 8
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

Find out more about Kahakuloa

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Kahakuloa. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.