Kaanapali Hillside Holidays from £1,229

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Your Kaanapali Hillside Holiday

Lock in a Kaanapali Hillside holiday package and get ready to experience all this lively city has to offer. Consider staying in the neighbourhood of Napili, which is great for walking, coastal beaches and hiking. A trip to Kaanapali Hillside is a terrific opportunity to do some sightseeing. Check out popular attractions like Kaanapali Beach, Kapalua Golf Club Plantation Course and D.T. Fleming Beach Park. Whoever you're taking a break with and whether your budget is big or small, your dream Kaanapali Hillside holiday is only clicks away with Expedia.

Top Kaanapali Hillside Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Residences at Kamaole Sands Resort

The Residences at Kamaole Sands Resort

4.5 out of 5
South Kihei
Price was £1,820, price is now £1,229 per person
£1,229
per person
7 Oct - 14 Oct
found 10 hours ago
Return flight included
San Francisco (SFO) to Kahului (OGG)
10/10 Exceptional! (2 reviews)
The place was very clean. The staff was very communicative and accommodating. I stayed Wednesday-Sunday and I extended my stay 1 night which was very fast and easy. They left us chairs and towels which was very nice for the beach. The place was very spacious for 2 people. If you want to cook this has plenty of counter space. The balcony had a partial ocean view which was very nice. Great value for your money. Check in/out was very easy. You can walk right to the best beaches around. Only Cons I can think of: Not a lot of blankets and the wifi in the bedroom didn’t really work, it was low signal. It would’ve been nice to watch Netflix from the bedroom. That’s the only negative I can think of.

Reviewed on 24 Feb 2026

Wailea Beach Villas

Wailea Beach Villas

4.5 out of 5
Wailea
Price was £5,100, price is now £3,990 per person
£3,990
per person
7 Oct - 14 Oct
found 10 hours ago
Return flight included
San Francisco (SFO) to Kahului (OGG)
9.8/10 Exceptional! (196 reviews)
Luxury condo right on Wailea beach with restaurants and shops nearby. I loved the beach view adult only pool, and that it was crowded.

Reviewed on 31 Jul 2026

Courtyard Maui Kahului Airport

Courtyard Maui Kahului Airport

4 out of 5
Price was £1,640, price is now £1,295 per person
£1,295
per person
7 Oct - 14 Oct
found 10 hours ago
Return flight included
San Francisco (SFO) to Kahului (OGG)
9.2/10 Wonderful! (1,000 reviews)

Makena Surf - CoralTree Residence Collection

Makena Surf - CoralTree Residence Collection

4 out of 5
Wailea
Price was £2,962, price is now £2,355 per person
£2,355
per person
7 Oct - 14 Oct
found 10 hours ago
Return flight included
San Francisco (SFO) to Kahului (OGG)
9.4/10 Exceptional! (116 reviews)
The property and the unit we stayed in was absolutely amazing. The balcony was right over the private beach and it’s also where the sunset so the view was beautiful. Right out the front door was the pool and spa and a few steps more and you’re on the beach. The unit was very clean and decorated so cute and had every amenity in the kitchen and bathrooms you could need. It was so peaceful and the beach was clean and water was prestige. The management company was super easy to deal with and loved my daily text of sunset and sunrise times and word of the day such a cute touch! I will definitely go back and will be requesting the same unit that was ideally positioned if possible. The entire property was beautiful and the secluded beach was amazing

Reviewed on 8 Jul 2026

Puunoa - CoralTree Residence Collection

Puunoa - CoralTree Residence Collection

4 out of 5
Save 100% on your flight
Price was £3,342, price is now £2,717 per person
£2,717
per person
7 Oct - 14 Oct
found 6 hours ago
Return flight included
San Francisco (SFO) to Kahului (OGG)
10/10 Exceptional! (15 reviews)
Having 3 bedrooms was awesome. Location of the property was amazing, the landscaping and cleanliness was amazing and perfect. BBQ Grills were cleaned daily by staff. Awesome snorkeling out back on the beach, freshwater pool, great place to shower off beach sand. Would stay again without hesitation.

Reviewed on 23 Jul 2021

Kaanapali Hillside Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Kahului Airport (OGG)
Max Temp Winter
24ºC
Max Temp Summer
27ºC
Top Sights
Kaanapali Beach, Black Rock and Kahekili Beach

Top hotels in Kaanapali Hillside

Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
3445 Lower Honoapiilani Hwy Lahaina HI
Fully refundableReserve now, pay when you stay
The price is £246 per night from 9 Aug to 10 Aug
£246
9 Aug - 10 Aug
includes taxes & fees
8.8/10 Excellent! (4,218 reviews)
"Great amenities. Courteous staff. Good value."

Reviewed on 2 Aug 2026

Aston Kaanapali Shores
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

4.5 out of 5
2365 Kaanapali Pkwy Lahaina HI
Fully refundableReserve now, pay when you stay
The price is £396 per night from 21 Aug to 22 Aug
£396
21 Aug - 22 Aug
includes taxes & fees
The Westin Maui Resort & Spa, Ka'anapali
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
2780 Kekaa Dr Lahaina HI
Fully refundableReserve now, pay when you stay
The price is £249 per night from 1 Sept to 2 Sept
£249
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (1,780 reviews)
"Property was awesome and very clean! The staff was very friendly and outgoing!"

Reviewed on 1 Aug 2026

Royal Lahaina Resort & Bungalows
See all 9,089 properties in Kaanapali Hillside
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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Frequently asked questions

How much does a Kaanapali Hillside travel package cost?
Custom build your Kaanapali Hillside package from as little as £1,229. Pick from any combination of flights, hotels and rental cars to build the escape you've been dreaming about for ages. Don't forget to add on a few activities!
If I'm not able to travel, can I cancel my Kaanapali Hillside travel package?
Don't worry if you're rethinking your Kaanapali Hillside travel package — it's possible to cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We realise life can sometimes throw a spanner in the works, so make your way to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.
How do I get a cheap travel package to Kaanapali Hillside?
If you love amazing deals, combine your bookings into a Kaanapali Hillside travel package. Whether you're chasing hotels, flights, tours or rental cars, you can browse and book them all in one place. You'll have loads of choice at your fingertips too. Expedia has more than 550 partner airlines and 1,000,000 properties globally to select from. Fly with who you want, check in where you like and save a bundle — now that's the ideal getaway!
Does Expedia offer Book Now, Pay Later Kaanapali Hillside holidays?
Yes, we do. Expedia has partnered with online lender Klarna to help you easily pay for your holiday in instalments. Simply pick the payment plan best suited to your needs during checkout and take the stress out of budgeting for your trip. Make sure you bundle your flights, car hire and hotel with Expedia to get the biggest bang for your holiday buck. Consider these flexible payment options below:

  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's monthly instalment plans. If paying just a little each month works for you, choose this option at checkout.
  • Pay in instalments holidays: If you'd prefer to pay off your escape in multiple transactions, holidays paid in instalments might be the right option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to hit that "book now" button, choose a low deposit holiday payment plan with Klarna.

Where should I stay in Kaanapali Hillside?
With so much to explore in Kaanapali Hillside, it's a good idea to secure a room in a hotel near its attractions. Kaanapali Beach, Whalers Village and Black Rock are some interesting ones to put on your itinerary.
What are the top hotels in Kaanapali Hillside?
Get your trip off to a great start by booking a room at Hyatt Regency Maui Resort & Spa. It's one of most sought-after properties in Kaanapali Hillside. Another welcoming option is Royal Lahaina Resort.
How far in advance should I book my Kaanapali Hillside holiday?
Browse Expedia to compare international airfares as soon as you know your travel dates. You can normally purchase a seat up to a year prior to departure. If it's too early for your preferred air carrier, or you have to book last minute, don't stress. The lowest prices to Kaanapali Hillside sometimes appear a few weeks before the date of departure.
What does an Expedia Kaanapali Hillside travel package include?
It all boils down to what type of trip you have in the works. Kaanapali Hillside holiday deals can include car rentals, hotels and flights. You can mix and match to find the bundle that suits your budget and style. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking a Kaanapali Hillside travel package?
When you book your flights, hotels and car rentals together, you'll land amazing discounts. Whether you're organising an island getaway in a villa or would rather stay in a convenient hotel in the city, Expedia will help make it happen.
Can I choose my airline with a Kaanapali Hillside Expedia travel package?
Expedia offers access to more than 550 partner airlines globally, so you certainly can. Simply pick your preferred carrier and put together the perfect Kaanapali Hillside escape.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.