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

Kahakuloa Holiday Rentals

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Our top choices for Kahakuloa holiday rentals

1. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,860 reviews)
"Wonderful Beach and right next door to kapalua!"
United States
joe
The price is NZ$511
includes taxes & fees
5 Sept - 6 Sept
Napili Shores Maui by OUTRIGGER

2. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (220 reviews)
"Great stay, thank you"
United States
Elizabeth
The price is NZ$595
includes taxes & fees
2 Sept - 3 Sept
Napili Village Hotel

3. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,278 reviews)
"Great location!"
United States
Shad
The price is NZ$465
includes taxes & fees
25 Aug - 26 Aug
Aston Kaanapali Shores

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 NZ$511
includes taxes & fees
1 Sept - 2 Sept
Unit 25 Waena Inn - Maui Private Suite

5. 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 NZ$558
includes taxes & fees
25 Aug - 26 Aug
Napili Sunset on the Beach

6. 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)
"Great location for our last night. Walk to the beach and close enough to the airport for an early flight."
United States
jeff s.
The price is NZ$742
includes taxes & fees
30 Aug - 31 Aug
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

7. Maui's best Surf, wdsurf, snorkeling by secluded beach+ AC.

Maui's best Surf, wdsurf, snorkeling by secluded beach+ AC.
Paia
9.6 out of 10, Exceptional, (57 reviews)
"This was an amazing place to stay! So close to the beach and downtown Paia - we would totally recommend this place to any of our friends! "
United States
Lizzie B.
The price is NZ$735
includes taxes & fees
25 Aug - 26 Aug
Maui's best Surf, wdsurf, snorkeling by secluded beach+ AC.

8. Yonegan Maui Getaways - Haiku - Unit 4

Yonegan Maui Getaways - Haiku - Unit 4
Haiku
9.0 out of 10, Wonderful, (22 reviews)
"Great location for driving the Road to Hana."
United States
Lisa
The price is NZ$577
includes taxes & fees
25 Aug - 26 Aug
Yonegan Maui Getaways - Haiku - Unit 4

9. 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 NZ$711
includes taxes & fees
5 Sept - 6 Sept
Updated Studio, AC, steps to beach

10. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (454 reviews)
"We love The Whaler!"
United States
Jacob
The price is NZ$1,063
includes taxes & fees
25 Aug - 26 Aug
The Whaler Resort Kaanapali Beach

11. Yonegan Maui Getaways - Haiku - Unit 3

Yonegan Maui Getaways - Haiku - Unit 3
Haiku-Pauwela
9.0 out of 10, Wonderful, (22 reviews)
"Perfect getaway for an island vacation if your not planning on staying in just your room. Made breakfast every morning close to beaches, turtles and shops"
United States
Jeremiah J.
The price is NZ$510
includes taxes & fees
25 Aug - 26 Aug
Yonegan Maui Getaways - Haiku - Unit 3

12. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,620 reviews)
"Great place"
United States
Luis MANUEL
The price is NZ$611
includes taxes & fees
1 Sept - 2 Sept
Aston Maui Kaanapali Villas

13. 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 NZ$705
includes taxes & fees
31 Aug - 1 Sept
Aston at The Whaler on Kaanapali Beach

14. 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 NZ$618
includes taxes & fees
26 Aug - 27 Aug
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

15. 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 NZ$787
includes taxes & fees
25 Aug - 26 Aug
Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!

16. 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 NZ$663
includes taxes & fees
6 Sept - 7 Sept
Beautiful Ocean and Outer Island Views! See Whales in season!

17. 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.
Romantic Oceanfront: Relax 25' from the Waves! 230+ Great Reviews!

18. Paia 2 Bedroom 2 Bathroom

Paia 2 Bedroom 2 Bathroom
Paia
9.2 out of 10, Wonderful, (14 reviews)
"The Condo was perfect for our stay! Two bedrooms and two bathrooms! Plenty of space and very clean and nicely furnished. The kitchen had everything we needed and more. The location was located in a great area. Our host was wonderful with tips and recommendations! We would definitely stay here again!"
United States
Sherri W.
The price is NZ$1,443
includes taxes & fees
2 Sept - 3 Sept
Paia 2 Bedroom 2 Bathroom

19. 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, (139 reviews)
"Clean and close to the beach and pool area! "
United States
Teri T.
The price is NZ$859
includes taxes & fees
3 Sept - 4 Sept
Napili Shores 1BR Condo – 2-Min Walk to Beach, Pools, AC & No Resort Fees

20. Bright, Beautiful, Remodeled Island Sands 505 Condo

Bright, Beautiful, Remodeled Island Sands 505 Condo
Wailuku
9.4 out of 10, Exceptional, (58 reviews)
"The property was very clean and well maintained! We enjoyed our stay. "
United States
Cindy B.
The price is NZ$1,330
includes taxes & fees
26 Aug - 27 Aug
Bright, Beautiful, Remodeled Island Sands 505 Condo
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Kahakuloa holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Kahakuloa. 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 Kahakuloa. 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 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 holiday 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 Kahakuloa short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Kahakuloa?

Yes, there are holiday rentals close to the most popular sights in Kahakuloa, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Kahakuloa has to offer?

Yonegan Maui Getaways - Haiku : This holiday home rental outside of Kahakuloa is located near the beach, and has 1 hot tub, a BBQ 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 favourite places to visit such as Kaanapali Beach and Napili Bay in the wider area.

What’s a holiday rental in Kahakuloa like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kahakuloa. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a family getaway.