Kaanapali Hillside holiday homes

We found 6,641 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Kaanapali Hillside to find one that's perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for spending time at your holiday home, which might include cable TV and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Kaanapali Hillside

Showing deals for:18 Dec - 25 Dec

Pool
Terrace/patio
Private kitchen
Property grounds
Exceptional
(23 reviews)

NEW LISTING! The Luxurious Bella Mare at Puamana Lahaina Maui

Lahaina

8% off
NZ$27,758
for 7 nights, 1 home
NZ$3,965 per night
includes taxes & fees
NEW LISTING! The Luxurious Bella Mare at Puamana Lahaina Maui
Your relaxing lanai
Meet your friends at the hot tub!
North garden 505 center next door
Kitchen bar
Exceptional
(134 reviews)

Mountainview with an updated island feel. Lahaina Shores 510 is waiting for you!

Lahaina

9% off
NZ$3,104
for 7 nights, 1 apartment
NZ$443 per night
includes taxes & fees
Mountainview with an updated island feel. Lahaina Shores 510 is waiting for you!
Security Gates to the Beach
Sunset View
Room
Open Parking
Exceptional
(81 reviews)

The Napili Bay Resort - Ocean View #114 - Voted Most Beautiful Bay on Maui

Lahaina

7% off
NZ$4,150
for 7 nights, 1 apartment
NZ$593 per night
includes taxes & fees
The Napili Bay Resort - Ocean View #114 - Voted Most Beautiful Bay on Maui
Pool, BBQs, and minutes to beach!
Beach
Spacious Living Room
Pool
Exceptional
(72 reviews)

Kaanapali Royal 2BR Condo • Pool & Beach

Lahaina

7% off
NZ$8,925
for 7 nights, 1 apartment
NZ$1,275 per night
includes taxes & fees
Kaanapali Royal 2BR Condo • Pool & Beach
Aloha and Welcome to Napili Bay Unit 115!
115 is just steps to the sand. . .
Exterior
Outdoor dining
Exceptional
(100 reviews)

LIGHT & BREEZY Unit #115 Napili Bay! First floor corner unit, open lanai! BOOK!

Lahaina

7% off
NZ$3,250
for 7 nights, 1 apartment
NZ$464 per night
includes taxes & fees
LIGHT & BREEZY Unit #115 Napili Bay! First floor corner unit, open lanai! BOOK!
Exterior
Interior
Interior
Interior
Exceptional
(92 reviews)

#564-Black Rock & Pool View-Family Friendly-Beach Items Prov..

Lahaina

7% off
NZ$10,242
for 7 nights, 1 apartment
NZ$1,463 per night
includes taxes & fees
#564-Black Rock & Pool View-Family Friendly-Beach Items Prov..
Pool
Newly Remodeled Lobby
Interior
Interior
Exceptional
(118 reviews)

#557-Amazing Ocean View & Sunsets-Walk 2 Restaurants-Beach Items Provided

Lahaina

7% off
NZ$13,068
for 7 nights, 1 apartment
NZ$1,867 per night
includes taxes & fees
#557-Amazing Ocean View & Sunsets-Walk 2 Restaurants-Beach Items Provided
Property grounds
Living area
Pool
Living area
Exceptional
(67 reviews)

VIR #409 Upper West Maui Oceanfront Condo - Kahana

Lahaina

7% off
NZ$3,458
for 7 nights, 1 apartment
NZ$494 per night
includes taxes & fees
VIR #409 Upper West Maui Oceanfront Condo - Kahana
Outdoor dining
Outdoor dining
Bright, open living space that flows seamlessly to the lanai, bringing the beauty of the outdoors inside
Private kitchen
Excellent
(35 reviews)

Sunlit 2BR Island Haven Plantation Style

Lahaina

6% off
NZ$7,364
for 7 nights, 1 apartment
NZ$1,052 per night
includes taxes & fees
Sunlit 2BR Island Haven Plantation Style
Property grounds
Pool
Beach
Property grounds
Exceptional
(139 reviews)

Tranquil Ocean View on Quiet Side of Honua Kai

Lahaina

8% off
NZ$9,593
for 7 nights, 1 apartment
NZ$1,370 per night
includes taxes & fees
Tranquil Ocean View on Quiet Side of Honua Kai
Property grounds
Pool
The beach is a short walk away
Property grounds
Exceptional
(38 reviews)

Maui Eldorado Beachfront Resort - Apt I-101 - Two Bedroom Vacation Rental Condo

Lahaina

6% off
NZ$4,473
for 7 nights, 1 apartment
NZ$639 per night
includes taxes & fees
Maui Eldorado Beachfront Resort - Apt I-101 - Two Bedroom Vacation Rental Condo
Property grounds
Pool
Property grounds
Beach
Exceptional
(15 reviews)

The Whaler On Ka'anapali Beach, Partial Ocean View, 3 beds, sleeps 6, has AC

Lahaina

7% off
NZ$11,528
for 7 nights, 1 apartment
NZ$1,647 per night
includes taxes & fees
The Whaler On Ka'anapali Beach, Partial Ocean View, 3 beds, sleeps 6, has AC
Entrance area with dining & living area beyond
With the West Maui mountains behind the condo, there can be lots of rainbows!
View to the island of Lanai from 1st floor lanai
View of Kaanapali Plantation condos from golf course
Exceptional
(54 reviews)

20% off for 7 day stay! Panoramic view front row 2 story in Kaanapali Plantation

Lahaina

16% off
NZ$7,381
for 7 nights, 1 apartment
NZ$1,054 per night
includes taxes & fees
20% off for 7 day stay! Panoramic view front row 2 story in Kaanapali Plantation
Dining
Property grounds
Interior
Beach
Exceptional
(65 reviews)

Spacious 1 Bedroom 2 Bathroom w/ Amazing Panoramic View of Black Rock and Beach

Lahaina

11% off
NZ$7,546
for 7 nights, 1 apartment
NZ$1,078 per night
includes taxes & fees
Spacious 1 Bedroom 2 Bathroom w/ Amazing Panoramic View of Black Rock and Beach

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Kaanapali Hillside getaway

Learn about the unique charm of Kaanapali Hillside with a stay in a holiday home rental. This city has something for everyone. Kaanapali Beach and Whalers Village are just a couple of the must-see attractions in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Kaanapali Hillside

Do you want to find top things to see and do in the city? Venture out of your cosy holiday rental and check out everything that makes Kaanapali Hillside a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Kaanapali Kai Course at Kaanapali Golf Resort (1 mi / 1.6 km)
  • Kaanapali Golf Courses (1 mi / 1.6 km)
  • Kapalua Resort (5.1 mi / 8.1 km)
  • Kapalua Golf Club Plantation Course (6.1 mi / 9.8 km)
  • Kahili Golf Course (12.7 mi / 20.5 km)
  • The Dunes at Maui Lani (13.7 mi / 22.1 km)

Exploring the natural features in Kaanapali Hillside

Whether you're an active traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Kaanapali Hillside. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Kaanapali Beach (1.3 mi / 2.1 km)
  • Kahekili Beach (1 mi / 1.6 km)
  • Black Rock (1.1 mi / 1.8 km)
  • Honokowai Beach Park (1.9 mi / 3 km)
  • Kahana Beach (3 mi / 4.8 km)
  • Baby Beach (3.2 mi / 5.2 km)

Transport options to and around Kaanapali Hillside

The nearest airport is in Kapalua, HI (JHM-West Maui), located 2.4 mi (3.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Kahului, HI (OGG), which is 15.8 mi (25.5 km) away.

Frequently asked questions

What is the best area to stay in Kaanapali Hillside when booking a holiday rental?
When considering a holiday rental in Kaanapali Hillside, a popular area to stay is near the beachfront, where you can enjoy stunning views of the ocean and easy access to the beach. This neighbourhood is known for its beautiful landscapes and a laid-back atmosphere, making it ideal for relaxation.In this area, you will find a variety of properties ranging from luxurious villas to more modest condos, suiting a range of budgets and preferences. The proximity to attractions such as the iconic Black Rock, renowned for its excellent snorkelling opportunities, and Whalers Village, a charming open-air shopping centre with a mix of dining and retail options, enhances the appeal of staying in Kaanapali Hillside.Additionally, the scenic walking paths along the coastline provide a wonderful opportunity for both leisurely strolls and more active pursuits, further enriching your holiday experience.
What are the top attractions in Kaanapali Hillside?
In Kaanapali Hillside, visitors can enjoy a variety of attractions that showcase the natural beauty and cultural richness of the area. The stunning Kaanapali Beach, known for its golden sands and clear waters, is a major highlight and great for sunbathing, swimming, and various water sports. Nearby, the historic Whalers Village offers shopping, dining, and cultural events, providing a glimpse into the region's whaling history.For those interested in outdoor activities, the scenic hiking trails in the surrounding hills provide breathtaking views of the coastline and the Pacific Ocean. Additionally, the iconic Black Rock, located at the north end of Kaanapali Beach, is a popular spot for cliff diving and snorkelling, attracting both thrill-seekers and marine life enthusiasts.Cultural experiences can be found in nearby Lahaina, a charming town rich in history and home to art galleries, restaurants, and the famous Banyan Tree Park.
Are all fees included in the Kaanapali Hillside holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Kaanapali Hillside holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Kaanapali Hillside with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Kaanapali Hillside holiday homes?
You can find great discounts on holiday homes in Kaanapali Hillside on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Kaanapali Hillside holiday home booking on Bookabach?
To find Kaanapali Hillside holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Kaanapali Hillside?
A long-stay holiday home in Kaanapali Hillside is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Kaanapali Hillside holiday home?
Book your Kaanapali Hillside holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Kaanapali Hillside?
Prices for holiday homes in Kaanapali Hillside vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Kaanapali Hillside to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.