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 Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (232 reviews)
"Great place! It’s quite and 30 seconds to the beach."
United States
Alysson E
The price is CA $273
CA $324 total
includes taxes & fees
Oct 5 - Oct 6
Napili Village Hotel

2. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,324 reviews)
"Great Stay"
United States
Roopa Rani
The price is CA $251
CA $340 total
includes taxes & fees
Sep 24 - Sep 25
Aston Kaanapali Shores

3. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,884 reviews)
"Love this place!"
United States
Diana
The price is CA $391
CA $464 total
includes taxes & fees
Oct 6 - Oct 7
Napili Shores Maui by OUTRIGGER

4. 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 $395
CA $468 total
includes taxes & fees
Sep 23 - Sep 24
Napili Sunset on the Beach

5. Unit 23 Waena Inn - Maui Private Suite

Unit 23 Waena Inn - Maui Private Suite
Wailuku
10.0 out of 10, Exceptional, (12 reviews)
"Fairly central location. Helpful and due to the length of our stay, offered for us to use washer/dryer, snorkels, beach towels. "
United States
Suzan F.
The price is CA $277
CA $461 total
includes taxes & fees
Oct 13 - Oct 14
Unit 23 Waena Inn - Maui Private Suite

6. Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (37 reviews)
"Good location for the Road to Hana and exploring Paia, hot tub was enjoyable."
United States
Matt
The price is CA $177
CA $421 total
includes taxes & fees
Oct 4 - Oct 5
Yonegan Maui Getaways - Haiku

7. Unit 22 Waena Inn - Maui Private Suite

Unit 22 Waena Inn - Maui Private Suite
Wailuku
9.8 out of 10, Exceptional, (38 reviews)
"The studio is super cute and in a convenient location, it was very clean and the check in process was really easy!"
United States
Claire R.
The price is CA $252
CA $431 total
includes taxes & fees
Sep 28 - Sep 29
Unit 22 Waena Inn - Maui Private Suite

8. Updated Studio, AC, steps to beach

Updated Studio, AC, steps to beach
Lahaina
9.8 out of 10, Exceptional, (159 reviews)
"Wonderful place to stay. Our host Evelyn very kindly allowed us to extend our stay with 0 issues after the recent Kona storm. We had a great time and experience - fully recommend. "
United States
MeMe C.
The price is CA $240
CA $569 total
includes taxes & fees
Oct 6 - Oct 7
Updated Studio, AC, steps to beach

9. Napili Shores 1BR Condo – 2-Min Walk to Beach, Pools, AC & No Resort Fees

Napili Shores 1BR Condo – 2-Min Walk to Beach, Pools, AC & No Resort Fees
Lahaina
9.8 out of 10, Exceptional, (140 reviews)
"After several days at a nearby resort, our stay here was exactly what we were hoping for. Quaint, quiet, less crowded, and old Hawaii charm. The apartment was very comfortable and had everything we needed. The grounds were beautiful and we loved being able to walk to Napili and Kapalua Bay. The we worst part was having to leave. We will definitely stay here again!"
United States
Shannon D.
The price is CA $315
CA $740 total
includes taxes & fees
Oct 1 - Oct 2
Napili Shores 1BR Condo – 2-Min Walk to Beach, Pools, AC & No Resort Fees

10. Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC
Lahaina
8.6 out of 10, Excellent, (109 reviews)
"Everything was great !"
United States
Michael
The price is CA $147
CA $1,088 total
includes taxes & fees
Oct 9 - Oct 10
Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

11. Condo w/ Lanai at Beginning of Road to Hana!

Condo w/ Lanai at Beginning of Road to Hana!
Paia
9.2 out of 10, Wonderful, (45 reviews)
"This was the perfect stay to start the Road to Hana and the town of Paia is so lovely and had a lot of food options. The beaches around this area were some of our favorite. If you can, make a reservation at Mamas Fishhouse or try and walk in around lunch time-it’s worth every penny! "
United States
Kiana C.
The price is CA $177
CA $593 total
includes taxes & fees
Oct 5 - Oct 6
Condo w/ Lanai at Beginning of Road to Hana!

12. Beautiful Ocean and Outer Island Views! See Whales in season!

Beautiful Ocean and Outer Island Views! See Whales in season!
Lahaina
9.4 out of 10, Exceptional, (92 reviews)
"The room was clean, the view from the balcony was awesome, and the overall experience was great. I'd recommend the place."
United States
Jasdeep Singh
The price is CA $125
CA $510 total
includes taxes & fees
Oct 6 - Oct 7
Beautiful Ocean and Outer Island Views! See Whales in season!

13. Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!

Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!
Lahaina
9.8 out of 10, Exceptional, (276 reviews)
"Amazing trip!"
United States
Eric L.
The price is CA $196
CA $681 total
includes taxes & fees
Sep 27 - Sep 28
Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!

14. Hale Nihi - Paia, Maui

Hale Nihi - Paia, Maui
Paia
9.6 out of 10, Exceptional, (65 reviews)
"Very convenient place to stay within walking distance to activities and beach. "
United States
Chameil H.
The price is CA $278
CA $662 total
includes taxes & fees
Oct 1 - Oct 2
Hale Nihi - Paia, Maui

15. Direct Oceanfront ground floor - Kuleana 706

Direct Oceanfront ground floor - Kuleana 706
Lahaina
9.6 out of 10, Exceptional, (135 reviews)
"Wonderful property, great support team from Epic Realty. everything was wonderful. We stayed at Kuleana Resort 4 times, and we've recommended it to several of our friend, and we will stay there again if we have a chance."
United States
Margarita R.
The price is CA $231
CA $1,218 total
includes taxes & fees
Oct 1 - Oct 2
Direct Oceanfront ground floor - Kuleana 706

16. Top floor! Direct view! Sleeps 6! Highly Desirable! #213

Top floor! Direct view! Sleeps 6! Highly Desirable! #213
Lahaina
9.4 out of 10, Exceptional, (150 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Aloha, we had the most amazing experience all around as a family of 5. Valerie went above and beyond in the front office and was so friendly and kind. She suggested many places to eat and snorkel. David kept the property looking great and was...
United States
Ryan T.
The price is CA $212
CA $786 total
includes taxes & fees
Sep 23 - Sep 24
Top floor! Direct view! Sleeps 6! Highly Desirable! #213

17. Cute and Cozy Ground Floor! Beach access! Great Location! #113

Cute and Cozy Ground Floor! Beach access! Great Location! #113
Lahaina
9.0 out of 10, Wonderful, (24 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Very chill and relaxed property with a great view. In a prime location."
United States
Kiele P.
The price is CA $143
CA $612 total
includes taxes & fees
Oct 4 - Oct 5
Cute and Cozy Ground Floor! Beach access! Great Location! #113

18. Direct Ocean Front~Kaanapali Beach~West Maui Paradise Welcomes You!

Direct Ocean Front~Kaanapali Beach~West Maui Paradise Welcomes You!
Lahaina
9.8 out of 10, Exceptional, (177 reviews)
"We truly enjoyed our stay in Maui. The room was perfect, and just as advertised. Seeing the sea turtles from the balcony and the amazing sunsets were some of our favorite parts of the trip. You literally cannot get any closer to the water, which was great at night, listening to the waves crash. Looking forward to our next trip!"
United States
Anthony P.
The price is CA $176
CA $590 total
includes taxes & fees
Sep 23 - Sep 24
Direct Ocean Front~Kaanapali Beach~West Maui Paradise Welcomes You!

19. Yonegan Maui Getaways - Haiku - Unit 6

Yonegan Maui Getaways - Haiku - Unit 6
Haiku-Pauwela
9.2 out of 10, Wonderful, (42 reviews)
"Everything was great."
United States
Bryan
The price is CA $172
CA $436 total
includes taxes & fees
Oct 1 - Oct 2
Yonegan Maui Getaways - Haiku - Unit 6

20. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (474 reviews)
"the staff were great and very welcoming, it had everything we needed whilst we were there"
United Kingdom
Sam
The price is CA $343
CA $919 total
includes taxes & fees
Oct 18 - Oct 19
The Whaler Resort Kaanapali Beach
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 Napili Bay 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.