Kaanapali holiday rentals

We found 6,505 holiday rentals — enter your dates for availability
Select from 28 houses, 1476 flats and other holiday rentals to find the perfect place for your stay in Kaanapali. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as Wi-Fi and a hot tub. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Kaanapali

Showing deals for:6 Nov - 13 Nov

Property grounds
Room
Outdoor dining
Pool
Exceptional
(30 reviews)

'PONO PLANTATION COTTAGE' WINTER IN PARADISE-3 BEDROOM

Lahaina

7% off
S$4,545
for 7 nights, 1 cottage
S$649 per night
includes taxes & fees
'PONO PLANTATION COTTAGE' WINTER IN PARADISE-3 BEDROOM
Living area
Dining from your private lanai
Pool
Recently updated kitchen
Exceptional
(102 reviews)

Updated Ocean View 2br/2ba Oceanfront Condo with Sand Beach

Lahaina

7% off
S$4,306
for 7 nights, 1 apartment
S$615 per night
includes taxes & fees
Updated Ocean View 2br/2ba Oceanfront Condo with Sand Beach
Outdoor dining
Pool
Private kitchen
Interior
Exceptional
(135 reviews)

West Maui, Kahana Sunset, Ocean View with AC, Private Beach

Lahaina

7% off
S$3,857
for 7 nights, 1 apartment
S$551 per night
includes taxes & fees
West Maui, Kahana Sunset, Ocean View with AC, Private Beach
One of the 2 pools with a cabana, if you prefer shade
Living room with big TV and even bigger view
View from Guest Bedroom to Lanai.
Master
Exceptional
(124 reviews)

Oceanfront Property - 60 feet from the ocean. Beautiful views, free WiFi

Lahaina

7% off
S$4,895
for 7 nights, 1 apartment
S$699 per night
includes taxes & fees
Oceanfront Property - 60 feet from the ocean. Beautiful views, free WiFi
Interior
Terrace/patio
Room
Whaler's beautiful inner courtyard
Exceptional
(101 reviews)

LOVE DA, THE WHALER # 1018, BLACK ROCK OCEAN VIEW STUDIO!!

Lahaina

5% off
S$4,220
for 7 nights, 1 apartment
S$603 per night
includes taxes & fees
LOVE DA, THE WHALER # 1018, BLACK ROCK OCEAN VIEW STUDIO!!
The Whaler's large beachfront swimming pool.
Property grounds
newly remodeled  dining and kitchen area
Tropical and lush The Whaler condo #860 features this spectacular view from every room.
Exceptional
(53 reviews)

Panoramic sea view

Lahaina

7% off
S$5,419
for 7 nights, 1 apartment
S$774 per night
includes taxes & fees
Panoramic sea view
Property grounds
Pool
Fully Stocked Kitchen
Property grounds
Exceptional
(15 reviews)

Luana 15D: Upper-Floor 3 Bed Villa w/ Private Lanai, BBQ & Garage

Kaanapali

5% off
S$11,270
for 7 nights, 1 apartment
S$1,610 per night
includes taxes & fees
Luana 15D: Upper-Floor 3 Bed Villa w/ Private Lanai, BBQ & Garage
Room
Pool
Property grounds
Property grounds
Exceptional
(201 reviews)

The Whaler 814, Black Rock, All 5 Stars. Ocean and Beachfront Views

Lahaina

6% off
S$4,500
for 7 nights, 1 apartment
S$643 per night
includes taxes & fees
The Whaler 814, Black Rock, All 5 Stars. Ocean and Beachfront Views
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

5% off
S$2,890
for 7 nights, 1 apartment
S$413 per night
includes taxes & fees
Sunlit 2BR Island Haven Plantation Style
Fully Stocked Kitchen
Pool
Private Lanai Entrance
Property grounds
Exceptional
(37 reviews)

Whaler at Kaanapali 420: 1 bed 1 bath Luxury Living on Kaanapali Beach

lahaina

5% off
S$4,807
for 7 nights, 1 apartment
S$687 per night
includes taxes & fees
Whaler at Kaanapali 420: 1 bed 1 bath Luxury Living on Kaanapali Beach
Disappearing pocket doors in the living room open to the large covered lanai
Say hello to your dream getaway in Luana Garden Villa 14D
Beautiful views from the balcony and primary bedroom
Starter set of paper products, cleaning supplies, detergents/soaps is provided
Exceptional
(15 reviews)

Luana 14D: 3 Bed Villa with Private BBQ & Garage + Resort Access

Kaanapali

5% off
S$10,845
for 7 nights, 1 apartment
S$1,549 per night
includes taxes & fees
Luana 14D: 3 Bed Villa with Private BBQ & Garage + Resort Access
Private kitchen
Beach
Dining
Private kitchen
Exceptional
(8 reviews)

Embark on an extraordinary escape to this remodeled condo at Ka'anapali Royal.

Lahaina

7% off
S$6,540
for 7 nights, 1 apartment
S$934 per night
includes taxes & fees
Embark on an extraordinary escape to this remodeled condo at Ka'anapali Royal.
Host a dinner at this gorgeous dining table for up to 6 people
Aloha from Hokulani 836! Prepare to be dazzled by the remarkable ocean views
Stainless steel appliances with the fridge featuring a water filter & ice maker
Swim through the caves and waterfalls at the Family Pool
Exceptional
(107 reviews)

Hokulani 836 at Honua Kai Resort ~ Extra Large Lanai With Amazing Ocean Views

Kaanapali

5% off
S$7,999
for 7 nights, 1 apartment
S$1,143 per night
includes taxes & fees
Hokulani 836 at Honua Kai Resort ~ Extra Large Lanai With Amazing Ocean Views
Living area
Pool
Living area
Room
Exceptional
(71 reviews)

Ocean front Beach Resort Hale Nalu ~ ~

Lahaina

5% off
S$3,309
for 7 nights, 1 apartment
S$473 per night
includes taxes & fees
Ocean front Beach Resort Hale Nalu ~ ~
Interior
Interior
Exterior
Interior
Exceptional
(92 reviews)

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

Lahaina

7% off
S$5,682
for 7 nights, 1 apartment
S$812 per night
includes taxes & fees
#564-Black Rock & Pool View-Family Friendly-Beach Items Prov..
On-site Dukes Beach House restaurant located in front of the Hokulani tower
Hokulani family pool
Living area with large, comfortable sofa sleeper.
Actual view from our lanai (balcony) looking west toward the ocean!
Exceptional
(202 reviews)

100% OCEAN VIEWS FROM ALL ROOMS, Ka'anapali Hokulani #525 --<Thanksgiving Avail>

Lahaina

7% off
S$13,735
for 7 nights, 1 apartment
S$1,962 per night
includes taxes & fees
100% OCEAN VIEWS FROM ALL ROOMS, Ka'anapali Hokulani #525 --<Thanksgiving Avail>
Checkers and shuffleboard
Napili Shores coi pond
There are 6 gas barbecues on the property.
Kitchen (well equiped!)
Exceptional
(99 reviews)

Last Minute Special! $175/nt plus tax in April Napili Shores - C121 Studio

Lahaina

7% off
S$2,423
for 7 nights, 1 apartment
S$346 per night
includes taxes & fees
Last Minute Special! $175/nt plus tax in April Napili Shores - C121 Studio
Interior
Newly Remodeled Lobby
Exterior
Pool
Exceptional
(117 reviews)

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

Lahaina

7% off
S$7,605
for 7 nights, 1 apartment
S$1,086 per night
includes taxes & fees
#557-Amazing Ocean View & Sunsets-Walk 2 Restaurants-Beach Items Provided
Ground Floor #156 Dining Area for 4
Ground Floor Lanai
Ground Floor Master Bedroom with access to Lanai
#156 Ground Floor Kitchen
Exceptional
(58 reviews)

#156 Kaanapali Beach Paradise Condo

lahania

11% off
S$4,260
for 7 nights, 1 apartment
S$609 per night
includes taxes & fees
#156 Kaanapali Beach Paradise Condo
Pool
Large Open Living Area
Exterior detail
Stainless Steel Apliances
Wonderful
(45 reviews)

Maui Eldorado D200 Beautiful & Bright Corner Unit with Large Lanai

Kaanapali

5% off
S$5,543
for 7 nights, 1 apartment
S$792 per night
includes taxes & fees
Maui Eldorado D200 Beautiful & Bright Corner Unit with Large Lanai
Enjoy the view from the kitchen while preparing meals
Watch the whales, turtles and sail boats while sipping your morning coffee.
View from lanai.  If you look closely you may see a turtle in the water!
Dining room is ideal for a romantic dinner.  Complete with linens and tableware
Exceptional
(289 reviews)

Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014

Lahaina

7% off
S$6,211
for 7 nights, 1 apartment
S$887 per night
includes taxes & fees
Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014
Mahana at Kaanapali
Views of Molokai & Lanai
Free Shuffleboard
Ocean Views from the pool
Exceptional
(39 reviews)

Maui Westside Presents: Mahana 1003 - Beautiful Premium Studio Unit at Mahana

Kaanapali

5% off
S$3,424
for 7 nights, 1 apartment
S$489 per night
includes taxes & fees
Maui Westside Presents: Mahana 1003 - Beautiful Premium Studio Unit at Mahana
Living area
Enoy spectacular panoramic ocean views from our floor-to-ceiling windows!
Lobby
Private kitchen
Exceptional
(105 reviews)

Another Get Me to Maui - Oceanfront condo, Spectacular Views~Winter specials!

Lahaina

7% off
S$4,540
for 7 nights, 1 apartment
S$649 per night
includes taxes & fees
Another Get Me to Maui - Oceanfront condo, Spectacular Views~Winter specials!
Pitch and Putt available
Pool with BBQ areas
Open space living
Large Living area with AC
Exceptional
(13 reviews)

Papakea J401 Stunning Ocean Views 2 bed Remodeled Top Floor Unit.

Lahaina

5% off
S$5,013
for 7 nights, 1 apartment
S$716 per night
includes taxes & fees
Papakea J401 Stunning Ocean Views 2 bed Remodeled Top Floor Unit.
  • 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

Take in the beachside beauty of Kaanapali

The beaches and surrounding scenery provide a peaceful ambience to your holiday home in Kaanapali. Renowned for its snorkelling, shopping and spas, this city welcomes all visitors. Kaanapali Beach and Whalers Village are just a couple of the must-see attractions. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Kaanapali

Do you want to find attractions to see in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Kaanapali has to offer. These 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 (1.2 mi / 1.9 km)
  • Kaanapali Golf Courses (1.2 mi / 1.9 km)
  • Kapalua Resort (4.8 mi / 7.7 km)
  • Kapalua Golf Club Plantation Course (5.8 mi / 9.4 km)
  • The Dunes at Maui Lani (14 mi / 22.6 km)
  • Kahili Golf Course (13.1 mi / 21.1 km)

Exploring the beaches and other natural features in Kaanapali

Kaanapali is famous for its beautiful ocean views, breathtaking sunsets and tropical setting. Whether you're an adventurous traveller or just want to appreciate the scenery, Kaanapali is a great place to get outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Kaanapali Beach (1.4 mi / 2.3 km)
  • Napili Bay (4.4 mi / 7.1 km)
  • Kahekili Beach (0.6 mi / 1 km)
  • Black Rock (1 mi / 1.6 km)
  • Kahana Beach (2.6 mi / 4.2 km)
  • Baby Beach (3.6 mi / 5.8 km)

Seasonal weather in Kaanapali

Travellers speak highly of Kaanapali for its snorkelling. If warm-weather activities are high on your list, September, August, October and July are the hottest months to visit, when temperatures average 25°C.

Transport options to and around Kaanapali

The nearest airport is in Kapalua, HI (JHM-West Maui), located 2.1 mi (3.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Kahului, HI (OGG), which is 16.1 mi (25.9 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Kaanapali?
Condos are the most popular type of holiday rental in Kaanapali, according to our data. Even if you've got something a little different in mind, Vrbo has properties in all sizes and shapes. Filter our options to find your perfect match.
How much does it cost to rent a holiday rental in Kaanapali?
Property type, length of stay and time of year are some of the conditions that can influence the price of a holiday home. Simply enter your travel dates to find your perfect escape. From cosy cabins to expansive luxury villas, all Vrbo holiday rentals provide unbeatable value.
How much does it cost to rent a beach house in Kaanapali?
When you travel and the style and size of the property will influence the cost of your beachside holiday rental. Type in your Kaanapali travel dates to see your options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use our filters to pick the features and amenities you want in your holiday home.
Are there pet-friendly holiday rentals in Kaanapali?
Good news. There are. You'll have a choice of 2,055 holiday rentals that welcome pets in Kaanapali on Vrbo. Our furry best friends also deserve a getaway, so simply use our search function for pet-friendly holiday rentals to book a place where your pooch can lap up the good times.
Can I rent a house with a pool in Kaanapali?
Add another level of fun to your getaway by booking your family into one of the 2,008 houses with a private pool in Kaanapali. Use our handy search filter to find the kind of property you want on Vrbo, and then spend lazy days frolicking in a swimming pool that's all your own.
What are popular rental amenities in Kaanapali?
A fireplace, a swimming pool and a firepit are the most popular rental amenities in Kaanapali. Whether you're taking to the road by yourself, with your spouse or as a family, Vrbo can help you find a holiday rental that fits your tastes with a load of extras you'll love.
Are there large group holiday rentals in Kaanapali?
Kaanapali has 124 holiday properties that can cater to 10 or more guests. These stays come with the space and privacy you need to share good times with loved ones.
Are there holiday rentals in Kaanapali that welcome kids?
Kaanapali has 2,051 family-friendly holiday homes to pick from. And tracking down a stay that welcomes kids is simple with Vrbo's "Properties good for families" filter. In addition to having the whole place to yourselves, you'll also get access to amenities and perks like bunk beds, full kitchens and yards.
What are the top attractions for families in Kaanapali?
You'll find lots of awesome things to see and do with the family in Kaanapali, including:
  • Kaanapali Beach
  • Black Rock
  • Napili Bay Beach
Are there one-bedroom holiday rentals in Kaanapali?
Yes, you can pick from 727 one-bedroom rentals in Kaanapali. Whether you're on the lookout for a cosy cottage or a fancy condo, Vrbo's one-bedroom properties are ideal if you don't need loads of space. One of the main perks of having your own pad? You'll never need to share your trip with strangers.
Can I find two-bedroom holiday rentals in Kaanapali?
Kaanapali has 790 two-bedroom holiday rentals for you to select from. Experience a holiday home with all the comfort and space you want at a price you'll love on Vrbo.
Are there holiday rentals with WiFi in Kaanapali?
Whether you want to keep up with the latest news, look over emails or update your social media, there are 1,087 holiday homes with WiFi in Kaanapali. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Kaanapali?
Select your travel dates and then use the filter tool to find holiday rentals with ac in Kaanapali on Vrbo. With 2,017 air-conditioned properties to choose from here, you can look forward to a comfortable and cool stay.
How old do you have to be to rent a holiday rental in Kaanapali?
The minimum required age is usually 16, 18 or 21. It can vary from one property to another on Vrbo, so check the rules of your chosen Kaanapali holiday rental before booking your escape.
How long can I rent a holiday rental in Kaanapali for?
It all depends on the Kaanapali property. To see a list of options offering extended stays, simply enter your dates and number of guests into the Vrbo search page. Look forward to having the entire place to yourself, as well as comforts such as a fully-equipped kitchen and outdoor spaces where the little ones can play. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.

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