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Our top choices for Kaanapali Hillside holiday rentals

1. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,632 reviews)
"Loved the waterfront cafe and beautiful beach!"
United States
Sabrina
The price is £260
includes taxes & fees
11 Oct - 12 Oct
Aston Maui Kaanapali Villas

2. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,313 reviews)
"We loved the grounds and people. Definitely will be booking to stay there, again."
United States
Scot
The price is £181
includes taxes & fees
24 Sept - 25 Sept
Aston Kaanapali Shores

3. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (467 reviews)
"Clean room, friendly staff, great location and views!"
United States
Luis A
The price is £477
includes taxes & fees
5 Oct - 6 Oct
The Whaler Resort Kaanapali Beach

4. Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!

Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!
Kannapali Beach Area
10.0 out of 10, Exceptional, (204 reviews)
"We loved our room!! The shower and bed were our highlights for sure. Definitely recommend staying here!!"
United States
Emily A.
The price is £409
includes taxes & fees
23 Sept - 24 Sept
Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!

5. 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 £582
includes taxes & fees
27 Sept - 28 Sept
Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

6. 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 nice studio apartment! Very clean and met our needs. Will definitely stay there again."
United States
MJ F.
The price is £571
includes taxes & fees
19 Sept - 20 Sept
Renovated Studio Ka’anapali Shores | Pools, AC, Beach Access

7. Summertime Special Prices!! Book Now!

Summertime Special Prices!! Book Now!
Kannapali Beach Area
10.0 out of 10, Exceptional, (172 reviews)
"Great communication from host. Condo was perfect with all the amenities one could need. Nice location convenient for walking, shopping, dining….Very quiet perfect for relaxing."
United States
Karen K.
The price is £445
includes taxes & fees
23 Sept - 24 Sept
Summertime Special Prices!! Book Now!

8. 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 £280
includes taxes & fees
6 Oct - 7 Oct
Beautiful Ocean and Outer Island Views! See Whales in season!

9. Kāʻanapali Ocean View Condo with Beachfront Cabana for Guests

Kāʻanapali Ocean View Condo with Beachfront Cabana for Guests
Kannapali Beach Area
10.0 out of 10, Exceptional, (170 reviews)
"Very peaceful and relaxing stay! "
United States
jason s.
The price is £368
includes taxes & fees
23 Sept - 24 Sept
Kāʻanapali Ocean View Condo with Beachfront Cabana for Guests

10. Top Floor! Direct Ocean View! Vaulted Ceilings! Winter Spec! #218

Top Floor! Direct Ocean View! Vaulted Ceilings! Winter Spec! #218
Lahaina
9.6 out of 10, Exceptional, (114 reviews)
"Great location to everything and timely easy communication ."
United States
Vicki P.
The price is £348
includes taxes & fees
25 Sept - 26 Sept
Top Floor! Direct Ocean View! Vaulted Ceilings! Winter Spec! #218

11. 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 £329
includes taxes & fees
4 Oct - 5 Oct
Cute and Cozy Ground Floor! Beach access! Great Location! #113

12. 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 £577
includes taxes & fees
5 Oct - 6 Oct
Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742

13. Charming 1BR Condo at Oceanfront Kaanapali Shores Unit 422

Charming 1BR Condo at Oceanfront Kaanapali Shores Unit 422
Lahaina
7.8 out of 10, Good, (91 reviews)
"Perfect stay!"
United States
Celyna L.
The price is £597
includes taxes & fees
27 Sept - 28 Sept
Charming 1BR Condo at Oceanfront Kaanapali Shores Unit 422

14. NEW Remodel Coming Oct 2026 • Ocean View • Papakea

NEW Remodel Coming Oct 2026 • Ocean View • Papakea
Lahaina
9.8 out of 10, Exceptional, (95 reviews)
"Great resort and location. A lot of affordable food choices."
United States
Mark J.
The price is £316
includes taxes & fees
11 Oct - 12 Oct
NEW Remodel Coming Oct 2026 • Ocean View • Papakea

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, (276 reviews)
"Amazing trip!"
United States
Eric L.
The price is £376
includes taxes & fees
19 Sept - 20 Sept
Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!

16. Kuleana Club - 509

Kuleana Club - 509
3.5 star property
Lahaina
The price is £272
includes taxes & fees
8 Oct - 9 Oct
Kuleana Club - 509

17. Remodeled Ocean View Studio at The Whaler 518-Kaanapali Beach-Walk to Dining

Remodeled Ocean View Studio at The Whaler 518-Kaanapali Beach-Walk to Dining
Kannapali Beach Area
9.6 out of 10, Exceptional, (80 reviews)
"Nice room. You can’t go wrong at the whaler. The shower leaked a little. Overall good experience"
United States
Alaba G.
The price is £695
includes taxes & fees
2 Oct - 3 Oct
Remodeled Ocean View Studio at The Whaler 518-Kaanapali Beach-Walk to Dining

18. 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 £656
includes taxes & fees
23 Sept - 24 Sept
Direct Oceanfront ground floor - Kuleana 706

19. 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, (1,159 reviews)
"All in all , it was an amazing experience, staff was great, room clean, trip was amazing."
United States
Brenda
The price is £436
includes taxes & fees
23 Sept - 24 Sept
The Westin Ka'anapali Ocean Resort Villas

20. Oceanview Corner Suite at Honua Kai – Sunshine & Serenity

Oceanview Corner Suite at Honua Kai – Sunshine & Serenity
Lahaina
9.2 out of 10, Wonderful, (126 reviews)
"Clean and well appointed property! The amenities at the resort were also wonderful. Will be back!"
United States
Kristen M.
The price is £648
includes taxes & fees
18 Sept - 19 Sept
Oceanview Corner Suite at Honua Kai – Sunshine & Serenity
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 Kaanapali Hillside Hotel Reviews

Find out more about Kaanapali Hillside

Everything you need to know about Kaanapali Hillside holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kaanapali Hillside holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 Kaanapali Hillside holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Kaanapali Hillside holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kaanapali Hillside holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kaanapali Hillside holiday rentals we have selected for you start as low as £171 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kaanapali Hillside rentals

At Expedia, we put the best Kaanapali Hillside holiday 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 Kaanapali Hillside 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 Kaanapali Hillside holiday.

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

Frequently asked questions

Can I find a holiday rental in Kaanapali Hillside?

Yes, there are holiday rentals close to the most popular sights in Kaanapali Hillside, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Kaanapali Hillside has to offer?

Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!: This holiday home rental outside of Kaanapali Hillside is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

What’s there to see and do in Kaanapali Hillside?

Explore the area and family-friendly sights such as Hawaii Nature Center of Iao Valley, or get out into nature at a spot like Kaanapali Beach. Whalers Village and Napili Bay are other popular places to visit in the area.

What’s a holiday rental in Kaanapali Hillside like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kaanapali Hillside. Holiday rentals feature amenities like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for family gatherings.