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, (1,856 reviews)
"Wonderful Beach and right next door to kapalua!"
United States
joe
The price is CA $313
CA $372 total
includes taxes & fees
Sep 2 - Sep 3
Napili Shores Maui by OUTRIGGER

2. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,267 reviews)
"Great location!"
United States
Shad
The price is CA $290
CA $385 total
includes taxes & fees
Aug 26 - Aug 27
Aston Kaanapali Shores

3. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (219 reviews)
"Great stay, thank you"
United States
Elizabeth
The price is CA $419
CA $497 total
includes taxes & fees
Sep 15 - Sep 16
Napili Village Hotel

4. Unit 25 Waena Inn - Maui Private Suite

Unit 25 Waena Inn - Maui Private Suite
Wailuku
9.8 out of 10, Exceptional, (16 reviews)
"Great place "
United States
Noah S.
The price is CA $255
CA $429 total
includes taxes & fees
Sep 1 - Sep 2
Unit 25 Waena Inn - Maui Private Suite

5. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (450 reviews)
"We love The Whaler!"
United States
Jacob
The price is CA $314
CA $877 total
includes taxes & fees
Aug 22 - Aug 23
The Whaler Resort Kaanapali Beach

6. Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (657 reviews)
"Clean room amd friendly staff."
United States
Chris
The price is CA $388
CA $460 total
includes taxes & fees
Aug 24 - Aug 25
Napili Sunset on the Beach

7. 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 $273
CA $453 total
includes taxes & fees
Aug 26 - Aug 27
Unit 23 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, (157 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 $236
CA $590 total
includes taxes & fees
Sep 5 - Sep 6
Updated Studio, AC, steps to beach

9. 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, (275 reviews)
"Amazing trip!"
United States
Eric L.
The price is CA $180
CA $652 total
includes taxes & fees
Aug 26 - Aug 27
Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!

10. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,618 reviews)
"Great place"
United States
Luis MANUEL
The price is CA $318
CA $501 total
includes taxes & fees
Sep 8 - Sep 9
Aston Maui Kaanapali Villas

11. 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, (90 reviews)
"Overall a 4/5 experience! I would stay here again without a doubt. Simple check-in process, attentive host, great ocean views, and a well equipped condo. The only drawback I can think of was in regards to some of the aging furnishings. "
United States
Timo S.
The price is CA $128
CA $540 total
includes taxes & fees
Aug 24 - Aug 25
Beautiful Ocean and Outer Island Views! See Whales in season!

12. Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach
4.0 star property
Lahaina
9.2 out of 10, Wonderful, (1,555 reviews)
"Lovely place with full amenities and walk out patio in the lawn. Would definitely book again!"
United States
Heidi
The price is CA $250
CA $582 total
includes taxes & fees
Aug 31 - Sep 1
Aston at The Whaler on Kaanapali Beach

13. OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
Wailuku
9.4 out of 10, Exceptional, (174 reviews)
"Nice place and conviently located"
United States
Mike M.
The price is CA $164
CA $521 total
includes taxes & fees
Aug 26 - Aug 27
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

14. Renovated Studio Ka’anapali Shores | Pools, AC, Beach Access

Renovated Studio Ka’anapali Shores | Pools, AC, Beach Access
lahaina
9.8 out of 10, Exceptional, (21 reviews)
"It was a great resort We will be back for sure"
United States
Gregory M.
The price is CA $156
CA $1,091 total
includes taxes & fees
Sep 8 - Sep 9
Renovated Studio Ka’anapali Shores | Pools, AC, Beach Access

15. 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, (108 reviews)
"Lovely room in a great location. Check in and check out were super easy, great amenities"
United States
Michaela F.
The price is CA $156
CA $1,091 total
includes taxes & fees
Sep 5 - Sep 6
Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

16. Romantic Oceanfront: Relax 25' from the Waves! 230+ Great Reviews!

Romantic Oceanfront: Relax 25' from the Waves! 230+ Great Reviews!
Lahaina
9.8 out of 10, Exceptional, (238 reviews)
"Great communication, wonderful location, clean and great property!"
United States
Eric T.
The price is CA $247
CA $600 total
includes taxes & fees
Aug 25 - Aug 26
Romantic Oceanfront: Relax 25' from the Waves! 230+ Great Reviews!

17. A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Kuau
9.4 out of 10, Exceptional, (215 reviews)
"We had a great time! Everything was perfect. "
United States
Samantha S.
The price is CA $255
CA $614 total
includes taxes & fees
Aug 30 - Aug 31
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

18. Eco-Friendly Condo on Road to Hāna - Walk to Beach

Eco-Friendly Condo on Road to Hāna - Walk to Beach
Paia
10.0 out of 10, Exceptional, (18 reviews)
"We had a wonderful stay, our host was sweet"
United States
Nancy k.
The price is CA $275
CA $549 total
includes taxes & fees
Aug 24 - Aug 25
Eco-Friendly Condo on Road to Hāna - Walk to Beach

19. Direct Oceanfront ground floor - Kuleana 706

Direct Oceanfront ground floor - Kuleana 706
Lahaina
9.6 out of 10, Exceptional, (133 reviews)
"We had a pretty good stay. Condo is older but served its purpose. Beautiful view and really close to waters edge!"
United States
Susan N.
The price is CA $219
CA $1,207 total
includes taxes & fees
Sep 3 - Sep 4
Direct Oceanfront ground floor - Kuleana 706

20. Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742

Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742
Lahaina
8.8 out of 10, Excellent, (114 reviews)
"Great location Clean Room Great property"
United States
Robert T.
The price is CA $156
CA $1,091 total
includes taxes & fees
Aug 22 - Aug 23
Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742
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, kitchenware, and a coffee maker.

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.