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:13 Nov - 20 Nov

Pool
Room
Outdoor dining
Property grounds
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
Amazing view from your private lanai
Dining from your private lanai
Pool
Living area
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
K643 across hall from K642
Family pool, waterslide, grotto
BEACHFRONT HONUA KIA RESORT
K642 Dining
Exceptional
(19 reviews)

Maui Westside Presents: Honua Kai - Konea 642/643 4 bed ocean view sleeps 12

Kaanapali

5% off
S$15,340
for 7 nights, 1 apartment
S$2,191 per night
includes taxes & fees
Maui Westside Presents: Honua Kai - Konea 642/643 4 bed ocean view sleeps 12
Outdoor dining
Pool
Interior
Beautiful lush grounds.
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
Master
Living room with big TV and even bigger view
Two shuffle board courts. Equipment available at office
One of the 2 pools with a cabana, if you prefer shade
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
Whaler's beautiful inner courtyard
Terrace/patio
Room
Interior
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!!
Open kitchen with stainless steel Bosch appliances and granite counter tops.
Evening Bliss.
Spacious living room with new floors and open kitchen.
Enjoy home cooked meals on the lanai with family and the West Maui Mountains!
Exceptional
(151 reviews)

GREAT VALUE! Huge Upgraded 765 Sqft 1 Bed TOP FLOOR Penthouse! 5 star AVG RATING

Lahaina

7% off
S$3,470
for 7 nights, 1 apartment
S$496 per night
includes taxes & fees
GREAT VALUE! Huge Upgraded 765 Sqft 1 Bed TOP FLOOR Penthouse! 5 star AVG RATING
Beautiful views from the balcony and primary bedroom
Say hello to your dream getaway in Luana Garden Villa 14D
Starter set of paper products, cleaning supplies, detergents/soaps is provided
Beautiful granite kitchen island with bar seating & tropical outdoor views
Wonderful
(16 reviews)

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

Kaanapali

5% off
S$10,639
for 7 nights, 1 apartment
S$1,520 per night
includes taxes & fees
Luana 14D: 3 Bed Villa with Private BBQ & Garage + Resort Access
Fully Stocked Kitchen
Pool
Private Lanai Entrance
Ocean Views
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
Property grounds
Pool
Property grounds
Lobby
Exceptional
(201 reviews)

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

Lahaina

6% off
S$4,579
for 7 nights, 1 apartment
S$654 per night
includes taxes & fees
The Whaler 814, Black Rock, All 5 Stars. Ocean and Beachfront Views
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
Make a delicious meal in this spacious kitchen looking out to the tropical views.
Exceptional
(107 reviews)

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

Kaanapali

5% off
S$7,994
for 7 nights, 1 apartment
S$1,142 per night
includes taxes & fees
Hokulani 836 at Honua Kai Resort ~ Extra Large Lanai With Amazing Ocean Views
18 foot ceilings throughout condo provide spacious feeling.
The water is so close, you can hear the surf!
Manicured putting greens, fun for the whole family.
Play shuffle board or lounge to the sound of the swaying palms.
Exceptional
(87 reviews)

Oceanfront with Million-Dollar View and NO FEES. LAST MINUTE 20% off Jun 4-23.

Lahaina

7% off
S$3,924
for 7 nights, 1 apartment
S$561 per night
includes taxes & fees
Oceanfront with Million-Dollar View and NO FEES. LAST MINUTE 20% off Jun 4-23.
Private kitchen
Beach
Dining
Property grounds
Exceptional
(8 reviews)

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

Lahaina

7% off
S$6,579
for 7 nights, 1 apartment
S$940 per night
includes taxes & fees
Embark on an extraordinary escape to this remodeled condo at Ka'anapali Royal.
Living area
Pool
Room
Living area
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 ~ ~
Pool
Interior
Interior
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..
Exterior
Newly Remodeled Lobby
Interior
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
The view as you enter your luxury suite
Watch the whales, turtles and sail boats while sipping your morning coffee.
Dining room is ideal for a romantic dinner.  Complete with linens and tableware
View from lanai.  If you look closely you may see a turtle in the water!
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
Front Lobby
Views of Molokai & Lanai
Ocean Views from the pool
Free Shuffleboard
Exceptional
(39 reviews)

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

Kaanapali

5% off
S$3,074
for 7 nights, 1 apartment
S$439 per night
includes taxes & fees
Maui Westside Presents: Mahana 1003 - Beautiful Premium Studio Unit at Mahana
Lobby
Enoy spectacular panoramic ocean views from our floor-to-ceiling windows!
Enjoy the oceanfront pool
Living area
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!
can see Lanai and Moloka"i
Interior
Pool
Private kitchen
Exceptional
(238 reviews)

Peace of Heaven Oceanfront 180 Degree of ocean front views/Kuleana unit 616

Lahaina

7% off
S$3,321
for 7 nights, 1 apartment
S$474 per night
includes taxes & fees
Peace of Heaven Oceanfront 180 Degree of ocean front views/Kuleana unit 616
View from the condo looking west toward Lanai
Oceanfront Pool.  One of two on-property pools.
Our resort is beachfront - only steps to Kaanapali beach.
Castaway Cafe patio - live music Thurs - Sun
Exceptional
(138 reviews)

A403 - Spacious 1 Bedroom, 2 King Bed, Garden and Partial Ocean Views

Lahaina

7% off
S$3,472
for 7 nights, 1 apartment
S$496 per night
includes taxes & fees
A403 - Spacious 1 Bedroom, 2 King Bed, Garden and Partial Ocean Views
Dining
Pool
Interior
Property grounds
Exceptional
(24 reviews)

Ultimate Luxury Oceanfront 2 bedroom 2 bath @ The Kaanapali Alii Resort

Lahaina

20% off
S$18,785
for 7 nights, 1 apartment
S$2,684 per night
includes taxes & fees
Ultimate Luxury Oceanfront 2 bedroom 2 bath @ The Kaanapali Alii Resort
Property grounds
Restaurant On Property
Living area
Exterior
Exceptional
(63 reviews)

Kaanapali Shores: 943 ~ Penthouse level with Stunning Ocean Views

Kaanapali

5% off
S$3,320
for 7 nights, 1 apartment
S$474 per night
includes taxes & fees
Kaanapali Shores: 943 ~ Penthouse level with Stunning Ocean Views
Complimentary beach gear including chairs, sand toys, boogie boards & cooler bag
Sliding glass doors open up to the large lanai & a sitting area
Entrance to the Maui Eldorado
Swim in 1 of 3 pools at the Eldorado
Exceptional
(81 reviews)

Maui Eldorado D206~ Spacious 1 Bed/2 Bath with island vibes & Ocean Views

Kaanapali

5% off
S$3,772
for 7 nights, 1 apartment
S$539 per night
includes taxes & fees
Maui Eldorado D206~ Spacious 1 Bed/2 Bath with island vibes & Ocean Views
  • 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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