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Kaanapali holiday rentals

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Best Kaanapali vacation rentals

Most recommended vacation rentals in Kaanapali

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Honua Kai - Hokulani 712 - Kaanapali - Balcony
Honua Kai - Hokulani 712
Kaanapali, Maui, HI, United States
9.4Wonderful(21)
Parking
Free Wi-Fi
Pool
Spa
$1,288+
View availability
Kbm Resorts: Honua Kai Hokulani Hkh-434 Mountain View Great Value Includes Rental Car - Kaanapali - Living room
Kbm Resorts: Honua Kai Hokulani Hkh-434 Mountain View Great Value Includes Rental Car
Kaanapali, Maui, HI, United States
Parking
Free Wi-Fi
Pool
Pet-friendly
$1,163+
View availability
Honua Kai - Konea 314 - Kaanapali - Living room
Honua Kai - Konea 314
Kaanapali, Maui, HI, United States
9.4Wonderful(22)
Parking
Free Wi-Fi
Pool
$1,036+
View availability
Kbm Resorts Free Car Honua Kai Hokulani Ocean View 2bedroom Condo Hkh-714 Ocean Views Beach Front Resort - Kaanapali - Living room
Kbm Resorts Free Car Honua Kai Hokulani Ocean View 2bedroom Condo Hkh-714 Ocean Views Beach Front Resort
Kaanapali, Maui, HI, United States
9.9Wonderful(20)
Parking
Free Wi-Fi
Pool
Pet-friendly
$996+
View availability
Kaanapali Shores - 259 - Kaanapali - Living room
Kaanapali Shores - 259
Kaanapali, Maui, HI, United States
9.8Wonderful(29)
Free Wi-Fi
Pool
Spa
$1,011+
View availability
Kaanapali Royal C202 - Kaanapali - Living room
Kaanapali Royal C202
Kaanapali, Maui, HI, United States
9.3Wonderful(16)
Free Wi-Fi
Pool
Spa
$677+
View availability
Kbm Resorts Free Car Honua Kai Hokulani Ocean View 2bedroom Condo Hkh-423 Gorgeous Studio With Ocean Views - Kaanapali - Pool
Kbm Resorts Free Car Honua Kai Hokulani Ocean View 2bedroom Condo Hkh-423 Gorgeous Studio With Ocean Views
Kaanapali, Maui, HI, United States
9.6Wonderful(13)
Parking
Free Wi-Fi
Pool
Pet-friendly
$1,036+
View availability
Maui Eldorado D200 - 2 Bedroom - Kaanapali - Living room
Maui Eldorado D200 - 2 Bedroom
Kaanapali, Maui, HI, United States
9.4Wonderful(21)
Parking
Free Wi-Fi
Pool
Spa
$940+
View availability
Kbm Resorts Free Car Kaanapali Shores Ks-260 Full Ocean View Beach Kid Amenities - Kaanapali - Building
Kbm Resorts Free Car Kaanapali Shores Ks-260 Full Ocean View Beach Kid Amenities
Kaanapali, Maui, HI, United States
9.3Wonderful(3)
Parking
Free Wi-Fi
Pool
Pet-friendly
$1,117+
View availability
Kbm Resorts Free Car The Whaler Wh1-1211 Sweeping Ocean Views Newly Furnished 2023 - Kaanapali - Pool
Kbm Resorts Free Car The Whaler Wh1-1211 Sweeping Ocean Views Newly Furnished 2023
Kaanapali, Maui, HI, United States
9.3Wonderful(3)
Parking
Free Wi-Fi
Pool
$981+
View availability
Maui Kaanapali Villas #B233 - Kaanapali
Maui Kaanapali Villas #B233
Kaanapali, Maui, HI, United States
8.3Very Good(23)
Free Wi-Fi
Pool
$861+
View availability
Mahana at Kaanapali - Kaanapali
Mahana at Kaanapali
Kaanapali, Maui, HI, United States
9.0Wonderful(20)
Pool
$649+
View availability
Maui Eldorado Resort - Kaanapali
Maui Eldorado Resort
Kaanapali, Maui, HI, United States
8.2Very Good(19)
Pool
$533+
View availability
Kbm Resorts Free Car Honua Kai Konea Hkk-203 Ocean View Fantastic Location - Kaanapali
Kbm Resorts Free Car Honua Kai Konea Hkk-203 Ocean View Fantastic Location
Kaanapali, Maui, HI, United States
Parking
Free Wi-Fi
Pool
Pet-friendly
$1,644+
View availability
Mahana at Kaanapali 618 - Kaanapali
Mahana at Kaanapali 618
Kaanapali, Maui, HI, United States
10Wonderful(3)
Pool
$771+
View availability
Maui Westside Properties - The Whaler 359 - Kaanapali
Maui Westside Properties - The Whaler 359
Kaanapali, Maui, HI, United States
9.7Wonderful(20)
Free Wi-Fi
Pool
Spa
$1,332+
View availability
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KAYAK’s insights for holiday rentals in Kaanapali

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Kaanapali with confidence.

Which month has the cheapest vacation rental rates in Kaanapali?

Vacation rentals are cheapest in Kaanapali in October, with average rates of $1,006. In comparison, February is the most expensive month, with prices at $1,948.

What is the cheapest day of the week to book a vacation rental in Kaanapali?

Tuesday offers the lowest rates in Kaanapali, with an average nightly price of $1,175. The highest prices are found on Wednesday, with average rates at $2,327.

How early should you book a vacation rental in Kaanapali?

Book at least 46 days before your stay begins to get the best price for your Kaanapali vacation rental.
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Good to know

Low season

April

High season

October

Average price (weeknight)

$1,386
Cheapest month to stay with an average 43% drop in price.
Most expensive month to stay with an average 87% rise in price.
Average Sun - Thu price over the last 2 weeks.

KAYAK's top tips for finding Kaanapali holiday rental deals

  • The apartments at Mahana are a great choice for those looking to have expansive ocean views from the comfort of their own space. Floor-to-ceiling windows look out across the shores of North Kaanapali Beach, where humpback whales regularly pass by just 50 to 100 yards out. Sea turtles and rainbow parrot fish can also be seen feeding on the reef below.
  • The Maui Kaanapali Villa is located just to the north of Black Rock Beach and is situated along three miles of white sandy shores. It comes with access to not one but two pools, a child’s wading area, and an activities center that is stocked to the brim with paddle boards, snorkel sets, and everything you could need to enjoy the ocean waters. There is also a café on site, as well as a convenience store, spa, fitness center, and even a complimentary trolley that leads to other resorts.
  • Diamond Resorts offers visitors traveling to Kaanapali a range of modern rental condos that come equipped with Tempurpedic mattresses, garden baths, walk-in showers, partial kitchens, and private balconies. They include sleeper sofas in their living areas, which allows them to accommodate a minimum of 4 adults. The resort also offers a range of dining options, from casual eateries to fine dining experiences, showcasing local flavors and international cuisine.
  • The Honua Kai offers oversized condos with open floor plans, ensuring you have plenty of space to stretch out and unwind in tranquil surroundings. Its windows look out across the ocean and the island of Lanai. High-end finished can be found here in abundance, from granite counters to Bosch stainless steel appliances to bathrooms with double vanity sinks, walk-in showers, and separate bathtubs.
  • The studios at the Hokulani Building overlook the tiki torches and on-site pool from their 100 square foot lanais. A bellman greets you at the door and leads you to accommodations that look out over Kaanapali Beach and Napili Bay.
  • Beachfront is the most popular holiday rental property amenity in Kaanapali
  • Holiday rentals in Kaanapali are around 82% more expensive than hotels on average. Search here to compare prices for all accommodation types in Kaanapali.
  • The best holiday rental properties in Kaanapali are Papakea D-105 - 179 October Specials - Maui No Ka Oi! (10.0, 24 reviews), Ocean View One Bedroom at Honua Kai!! (10.0, 33), and Whaler 412 Kaanapali Beach Remodeled 1bd. Black Rockviews,located On Quiet Side. (9.9, 23), based on ratings and reviews from real travellers.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Kaanapali for 7 days.
See more tips

FAQs when booking a holiday home in Kaanapali

  • What types of holiday rentals are available in Kaanapali?

    There are loads of different property types that you can make your holiday home in Kaanapali. You’ll find apartments, condos, cottages, houses, homestays, studios and villas.

  • Are there any pet-friendly holiday rentals in Kaanapali?

    There are a number of dog and pet-friendly Kaanapali holiday rentals, with around 5% allowing you to bring your pet along with you.

  • How much is a holiday rental in Kaanapali for tonight?

    In the last 72 hours, users have found Kaanapali holiday rentals for tonight for as low as $694. Search here for similar prices

  • How can I find holiday rentals near me in Kaanapali?

    Take a look at our holiday rentals map to find the best holiday rental homes near you.

  • What Kaanapali vacation rentals offer the most scenic views?

    The closest resort to the oceanfront on Kaanapali Beach is The Whaler, which offers studio apartment rentals with spanning views of Bay of Black Rock. Looking out across the ocean to Molokai, lucky visitors may be able to witness the annual whale migration.

  • What Kaanapali vacation rentals offer dining options nearby?

    Kaanapali Shores is a one bedroom, one bathroom apartment with ocean views, an inner courtyard, and resort-style pool. It is located within 2 minute walking distance to a full service grocery store, multiple restaurants, and a vast array of highly popular food trucks. Live music is featured on-site every Thursday along with a hula show.

  • Are there pet friendly Kaanapali house rentals?

    The Westin Kaanapali Ocean Resort is home to a number of villas that offer access to oceanfront swimming pools, hot tubs, whirlpools, fitness rooms, complimentary shuttles, and all the comforts of home. Along with all of this, the resort understands the importance of bringing along your furry family members and so offer pet friendly accommodations.

  • What Kaanapali vacation rentals are most centrally located?

    The Maui Eldorado condo invites travelers to stay right in the center of the world famous Kaanapali Beach. It is located on the Royal Kaanapali North Golf Course and offers the only private beach cabana around, as well as a complimentary golf cart shuttle service to transport you to the beach where you can enjoy swimming, water sports, and snorkeling.

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Where to stay in Kaanapali?

Our map will help you find the perfect place to stay in Kaanapali by showing you the exact location of each holiday rental.

Everything you need to know for your stay in Kaanapali

Popular hotel types in Kaanapali

Kaanapali last minute hotels

Kaanapali holiday rental deals. Search for holiday homes, apartments, condos, cabins, cottages, villas and more in Kaanapali. Find cheap holiday homes to rent in Kaanapali. KAYAK searches hundreds of travel sites to help you find and book a holiday rental in Kaanapali that suits you best.

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