Kaanapali Hillside Holiday Rentals from €255: Search Short-Term Rentals

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

Stunning Views & Tropical Tranquility 429 LS : This holiday home rental outside of Kaanapali Hillside is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

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Our top choices for Kaanapali Hillside holiday rentals

Napili Village Hotel

Lahaina

Patrick James

includes taxes & fees

7 Jul - 8 Jul

Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

North Kihei

Danniella

includes taxes & fees

6 Jul - 7 Jul

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

Wailuku

Chris P.

includes taxes & fees

30 Jun - 1 Jul

Bright, Beautiful, Remodeled Island Sands 505 Condo

Wailuku

Cindy B.

includes taxes & fees

1 Jul - 2 Jul

🤙 June-July-August SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE

North Kihei

Mike H.

includes taxes & fees

7 Jul - 8 Jul

Unit 25 Waena Inn - Maui Private Suite

Wailuku

Noah S.

includes taxes & fees

2 Jul - 3 Jul

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

North Kihei

Sylvia

includes taxes & fees

6 Jul - 7 Jul

Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

North Kihei

PC SHOP

includes taxes & fees

29 Jun - 30 Jun

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Top Kaanapali Hillside Hotel Reviews

Maui Beach Vacation Club

8/10 Good

"Everything is good except for the soft bed"

The Ritz-Carlton Maui, Kapalua

8/10 Good

"Staff was great, especially front desk (Margie Ruiz) bellmen, valet and pool. However the property has not "aged" well. Last time we were here it was perfect in every way. Since Marriott has take over the attention to "detail" is not there. Examples, pool deck not clean in the morning, frayed fringe on beds, AC hard to use, need for paint. Paying top price, should get top everything especially the look!"

Hilton Vacation Club Ka'anapali Beach Maui

10/10 Excellent

"This was a beautiful resort. The rooms were spacious and clean, there were walkable amenities and the staff were overall pretty fantastic. I would highly recommend staying here, and I am pretty picky about hotels. This was absolutely worth it!!"

Sheraton Maui Resort & Spa

8/10 Good

"Best location on Ka’Anapali! Loved walking to Whalers Village almost daily for our breakfast and dinners. Biggest gripe about the hotel is insane shortage on pool chairs- meaning 100% of them were “claimed” by 8am every day we were there!! We had to switch rooms based on finding a huge scurrying cockroach in our bed (I know - it’s Hawai’i but still…). They didn’t do anything to extra to accommodate us for troubles having to switch rooms. The bar food was actually really good. Gym equipment (elliptical and bikes) were broken and seriously outdated - they had chargers for the original I-Pod! But all that said, I would go back. They just need to tend to the property a little more in my opinion."

Royal Lahaina Resort & Bungalows

8/10 Good

"Great Grounds and Luau, but a Few Hiccups Rating: ⭐⭐⭐⭐☆ (4/5) The Highlights: Grounds, Beach, and Luau The grounds at The Royal Lahaina Resort and Bungalows are absolutely beautiful, and the pools are decent. One of the best parts was the beach—it’s very nice and, thankfully, not overcrowded at all. Another major highlight was the Myths of Maui Luau. It was great, and I definitely recommend splurging for the VIP experience! The Accommodations & Staff Most of the staff members we encountered were pleasant, with the exception of one evening front desk agent who could have been more helpful. As for the room, we stayed on the 9th floor of the tower. The rooms themselves were small but very clean. The beds were comfortable, and the A/C worked great, which is a must. However, we hit a bit of bad luck during our stay as the resort was being painted. Being up on the 9th floor, the smell of the paint was overwhelming. Food & Beverage Note A quick heads-up on the coffee shop: I wouldn't recommend the coffee here. It was very weak and tasted like it was mostly milk. The Verdict: Despite the paint fumes and the weak coffee, the beautiful location, great beach, and excellent luau made this a solid 4-star stay."

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 €255 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?

Stunning Views & Tropical Tranquility 429 LS: This holiday home rental outside of Kaanapali Hillside is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

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 Kahekili Beach are a couple of places you'll find in the wider 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.

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