Kaanapali holiday rentals

We found 6,554 holiday rentals — enter your dates for availability
Select from 28 houses, 1472 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

Games room
Interior
Outdoor dining
Room
Exceptional
(59 reviews)

Oceanfront Villa Turtle Cove Villa, Napili. Spectacular views. 5BR Sleeps 10 A/C

Lahaina

7% off
S$17,019
for 7 nights, 1 villa
S$2,431 per night
includes taxes & fees
Oceanfront Villa Turtle Cove Villa, Napili. Spectacular views. 5BR Sleeps 10 A/C
Outdoor dining
Room
Interior
Property grounds
Exceptional
(30 reviews)

'PONO PLANTATION COTTAGE' WINTER IN PARADISE-3 BEDROOM

Lahaina

7% off
S$4,507
for 7 nights, 1 cottage
S$644 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$4,398
for 7 nights, 1 apartment
S$628 per night
includes taxes & fees
Updated Ocean View 2br/2ba Oceanfront Condo with Sand Beach
K642 Kitchen
Family pool, waterslide, grotto
K643 across hall from K642
K642 Dining
Exceptional
(19 reviews)

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

Kaanapali

5% off
S$15,324
for 7 nights, 1 apartment
S$2,189 per night
includes taxes & fees
Maui Westside Presents: Honua Kai - Konea 642/643 4 bed ocean view sleeps 12
Room
Ocean front condo!!
Living area
Pool
Wonderful
(147 reviews)

Now This Truly is Maui!! Oceanfront & Pool views from lanai

Lahaina

7% off
S$1,767
for 7 nights, 1 apartment
S$252 per night
includes taxes & fees
Now This Truly is Maui!! Oceanfront & Pool views from lanai
Interior
Pool
Outdoor dining
Private kitchen
Exceptional
(135 reviews)

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

Lahaina

6% off
S$3,947
for 7 nights, 1 apartment
S$564 per night
includes taxes & fees
West Maui, Kahana Sunset, Ocean View with AC, Private Beach
Two shuffle board courts. Equipment available at office
Living room with big TV and even bigger view
Master
View from Guest Bedroom to Lanai.
Exceptional
(124 reviews)

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

Lahaina

7% off
S$4,983
for 7 nights, 1 apartment
S$712 per night
includes taxes & fees
Oceanfront Property - 60 feet from the ocean. Beautiful views, free WiFi
Whaler's beautiful inner courtyard
Terrace/patio
Room
Dining
Exceptional
(101 reviews)

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

Lahaina

5% off
S$4,309
for 7 nights, 1 apartment
S$616 per night
includes taxes & fees
LOVE DA, THE WHALER # 1018, BLACK ROCK OCEAN VIEW STUDIO!!
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
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$10,570
for 7 nights, 1 apartment
S$1,510 per night
includes taxes & fees
Luana 14D: 3 Bed Villa with Private BBQ & Garage + Resort Access
Huge master bedroom with king size bed and 42 inch flat-screen TV.
Evening Bliss.
Enjoy home cooked meals on the lanai with family and the West Maui Mountains!
Open kitchen with stainless steel Bosch appliances and granite counter tops.
Exceptional
(151 reviews)

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

Lahaina

7% off
S$3,532
for 7 nights, 1 apartment
S$505 per night
includes taxes & fees
GREAT VALUE! Huge Upgraded 765 Sqft 1 Bed TOP FLOOR Penthouse! 5 star AVG RATING
Stainless steel appliances with the fridge featuring a water filter & ice maker
Aloha from Hokulani 836! Prepare to be dazzled by the remarkable ocean views
Swim through the caves and waterfalls at the Family Pool
Host a dinner at this gorgeous dining table for up to 6 people
Exceptional
(108 reviews)

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

Kaanapali

5% off
S$8,076
for 7 nights, 1 apartment
S$1,154 per night
includes taxes & fees
Hokulani 836 at Honua Kai Resort ~ Extra Large Lanai With Amazing Ocean Views
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$4,896
for 7 nights, 1 apartment
S$699 per night
includes taxes & fees
Whaler at Kaanapali 420: 1 bed 1 bath Luxury Living on Kaanapali Beach
Property grounds
Pool
Lobby
Room
Exceptional
(201 reviews)

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

Lahaina

6% off
S$4,879
for 7 nights, 1 apartment
S$697 per night
includes taxes & fees
The Whaler 814, Black Rock, All 5 Stars. Ocean and Beachfront Views
Play shuffle board or lounge to the sound of the swaying palms.
The water is so close, you can hear the surf!
18 foot ceilings throughout condo provide spacious feeling.
Manicured putting greens, fun for the whole family.
Exceptional
(87 reviews)

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

Lahaina

7% off
S$4,007
for 7 nights, 1 apartment
S$572 per night
includes taxes & fees
Oceanfront with Million-Dollar View and NO FEES. LAST MINUTE 20% off Jun 4-23.
Private kitchen
Beach
Private kitchen
Dining
Exceptional
(8 reviews)

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

Lahaina

7% off
S$6,714
for 7 nights, 1 apartment
S$959 per night
includes taxes & fees
Embark on an extraordinary escape to this remodeled condo at Ka'anapali Royal.
Pool
Interior
Interior
Exterior
Exceptional
(92 reviews)

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

Lahaina

7% off
S$5,812
for 7 nights, 1 apartment
S$830 per night
includes taxes & fees
#564-Black Rock & Pool View-Family Friendly-Beach Items Prov..
Interior
Newly Remodeled Lobby
Exterior
Pool
Exceptional
(117 reviews)

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

Lahaina

7% off
S$7,783
for 7 nights, 1 apartment
S$1,112 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
Enjoy the view from the kitchen while preparing meals
Exceptional
(289 reviews)

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

Lahaina

7% off
S$6,339
for 7 nights, 1 apartment
S$906 per night
includes taxes & fees
Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014
Front Lobby
Views of Molokai & Lanai
Mahana at Kaanapali
Free Shuffleboard
Exceptional
(39 reviews)

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

Kaanapali

5% off
S$3,131
for 7 nights, 1 apartment
S$447 per night
includes taxes & fees
Maui Westside Presents: Mahana 1003 - Beautiful Premium Studio Unit at Mahana
Private kitchen
Enoy spectacular panoramic ocean views from our floor-to-ceiling windows!
Living area
Enjoy the oceanfront pool
Exceptional
(105 reviews)

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

Lahaina

7% off
S$4,635
for 7 nights, 1 apartment
S$662 per night
includes taxes & fees
Another Get Me to Maui - Oceanfront condo, Spectacular Views~Winter specials!
Our resort is beachfront - only steps to Kaanapali beach.
Oceanfront Pool.  One of two on-property pools.
You will be warmly greeted at check-in by MKV front desk staff.
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$3,533
for 7 nights, 1 apartment
S$505 per night
includes taxes & fees
A403 - Spacious 1 Bedroom, 2 King Bed, Garden and Partial Ocean Views
Interior
Pool
Dining
Lobby
Exceptional
(24 reviews)

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

Lahaina

20% off
S$18,714
for 7 nights, 1 apartment
S$2,673 per night
includes taxes & fees
Ultimate Luxury Oceanfront 2 bedroom 2 bath @ The Kaanapali Alii Resort
From the Lanai
Wedding Gazebo
Our new garden pool.
Expedia desk
Exceptional
(109 reviews)

30% discount for 7 plus night stays, 06/01/26 to 12/15/26, Great View,.......

Lahaina

22% off
S$2,406
for 7 nights, 1 apartment
S$344 per night
includes taxes & fees
30% discount for 7 plus night stays, 06/01/26 to 12/15/26, Great View,.......
Private kitchen
Say hello to your ultimate dream vacation in Hokulani 709!
Private kitchen
Your eyes will find paradise in every direction
Exceptional
(67 reviews)

Hokulani 709 at Honua Kai Resort ~ Big Wrap-Around Lanai With BBQ & Ocean Views

Kaanapali

5% off
S$9,464
for 7 nights, 1 apartment
S$1,352 per night
includes taxes & fees
Hokulani 709 at Honua Kai Resort ~ Big Wrap-Around Lanai With BBQ & 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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