Kaanapali Hillside Vacations from $693

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Your Kaanapali Hillside Vacation

Lock in a Kaanapali Hillside vacation package and get ready to experience all this lively city has to offer. Consider staying in the neighborhood 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 vacation is only clicks away with Expedia.

The Latest Kaanapali Hillside vacation packages

Price found within the past 48 hours. Click for updated prices.
Mana Kai Maui- Official Onsite Rental

Mana Kai Maui- Official Onsite Rental

3.5 out of 5
Save 100% on your flight
Price was $1,440, price is now $693 per person
$693
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
8.8/10 Excellent! (1,005 reviews)
Great relaxed spot at the head of a beautiful public beach. Stayed many times and always return.

Reviewed on Aug 29, 2025

Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
Save 100% on your flight
Price was $1,679, price is now $862 per person
$862
per person
Nov 5 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
8.2/10 Very Good! (790 reviews)
Nice grounds, beautiful views, friendly staff. It would have been nice if they had items like snorkel gear, coolers, beach chairs etc. for the guest to use. Also coffee should be complimentary and provided at check in for each day of stay. Other than that it was a very nice place. Would definitely recommend for a budget friendly place to stay.

Reviewed on Aug 26, 2025

Napili Kai Beach Resort

Napili Kai Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,922, price is now $1,152 per person
$1,152
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Kahului (OGG)
9.4/10 Exceptional! (1,003 reviews)
Staff was so friendly. Our room had the most beautiful view and was clean, updated and stunning!

Reviewed on Aug 27, 2025

Aston Maui Hill

Aston Maui Hill

3 out of 5
Save 100% on your flight
Price was $2,213, price is now $1,330 per person
$1,330
per person
Nov 5 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9/10 Wonderful! (816 reviews)
Condo was clean. Easy to check in and out. They have a shared grill that we used. All types of birds including chickens on property.

Reviewed on Aug 26, 2025

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
Price was $1,302, price is now $792 per person
$792
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
8.4/10 Very Good! (1,420 reviews)
Beautiful hotel, next to the best beach in Maui. Service was great and everything was nearby! Would definitely come back and would highly recommend!

Reviewed on Aug 29, 2025

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Kaanapali Hillside Hotel Deals

Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
3445 Lower Honoapiilani Hwy, Lahaina, HI
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $218 total per night from Sep 1 to Sep 2
$218 total
Sep 1 - Sep 2
Total with taxes and fees
Aston Kaanapali Shores
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
2780 Kekaa Dr, Lahaina, HI
Fully refundableReserve now, pay when you stay
$259 nightly
The price is $305 total per night from Sep 28 to Sep 29
$305 total
Sep 28 - Sep 29
Total with taxes and fees
8.2/10 Very Good! (1,391 reviews)
"Great!"

Reviewed on Aug 27, 2025

Royal Lahaina Resort & Bungalows
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
$471 nightly
The price is $556 total per night from Sep 17 to Sep 18
$556 total
Sep 17 - Sep 18
Total with taxes and fees
The Westin Maui Resort & Spa, Ka'anapali
See all 8,309 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 vacation package cost?
You'll find cheap prices from $693 on Expedia for your Kaanapali Hillside break. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Kaanapali Hillside costs.
What are the cheapest months to go to Kaanapali Hillside?
You can generally find reduced prices and greater availability in October, November and December. Explore our cheap Kaanapali Hillside vacation packages and you could score some excellent off-season deals.
How many days is enough for Kaanapali Hillside?
Generally, a handful of days is enough to go to the top sights during your Kaanapali Hillside vacation. But if you'd like to have some time to unwind or go on day tours, think about extending your itinerary.
How to find the best Kaanapali Hillside package deals?
Start your search for a Kaanapali Hillside package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Kaanapali Hillside package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Kaanapali Hillside escape underway.
Is it cheaper to book a Kaanapali Hillside vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays separately. Better still, you can tailor your Kaanapali Hillside getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Kaanapali Hillside?
If you're planning an impromptu Kaanapali Hillside vacation, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Kaanapali Hillside vacation packages?
Your Kaanapali Hillside break is meant to be a relaxing escape from your daily routine, not a source of money-related stress. So to allow you more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.