A beach with clear turquoise water, people swimming and sunbathing, and palm trees.

Kaanapali Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Kaanapali vacation rentals

A swimming pool with a curved design, surrounded by palm trees and lounge chairs, with a building in the background.

1. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,647 reviews)
"Great place will stay again!"
United States
Joseph
The price is CA $308
CA $493 total
includes taxes & fees
Nov 6 - Nov 7
Aston Maui Kaanapali Villas
A view of a beach with palm trees and a sailboat on the water.

2. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (498 reviews)
"We loved everything and the location was perfect!!"
United States
Lenore
The price is CA $349
CA $934 total
includes taxes & fees
Oct 18 - Oct 19
The Whaler Resort Kaanapali Beach
A tropical garden with a waterfall, lush greenery, and a gazebo.

3. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,381 reviews)
"Great Stay"
United States
Roopa Rani
The price is CA $329
CA $433 total
includes taxes & fees
Oct 28 - Oct 29
Aston Kaanapali Shores
A tropical garden with a waterfall, a gazebo, and lush vegetation.

4. Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC
Lahaina
8.6 out of 10, Excellent, (111 reviews)
"Everything was great !"
United States
Michael
The price is CA $139
CA $1,092 total
includes taxes & fees
Oct 16 - Oct 17
Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC
A resort with a pool, palm trees, and a view of the ocean.

5. The Westin Nanea Ocean Villas, Ka'anapali

The Westin Nanea Ocean Villas, Ka'anapali
4.0 star property
Lahaina
9.4 out of 10, Exceptional, (537 reviews)
"It was beautiful hotel and we love to walk to the beach."
United States
Maria
The price is CA $592
CA $703 total
includes taxes & fees
Oct 31 - Nov 1
The Westin Nanea Ocean Villas, Ka'anapali
A pool area with a waterfall, stone steps, and tropical plants.

6. Renovated Studio Ka’anapali Shores | Pools, AC, Beach Access

Renovated Studio Ka’anapali Shores | Pools, AC, Beach Access
lahaina
9.8 out of 10, Exceptional, (21 reviews)
"It was a nice studio apartment! Very clean and met our needs. Will definitely stay there again."
United States
MJ F.
The price is CA $139
CA $1,092 total
includes taxes & fees
Oct 17 - Oct 18
Renovated Studio Ka’anapali Shores | Pools, AC, Beach Access
A resort pool with red umbrellas, palm trees, and a view of the ocean.

7. OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (3,069 reviews)
"Such a lovely stay. The hotel is in a great location, everyone was very kind. I would definitely stay here again!"
United States
Andrea
The price is CA $399
CA $1,130 total
includes taxes & fees
Nov 15 - Nov 16
OUTRIGGER Honua Kai Resort & Spa
A modern kitchen with a central island, stainless steel appliances, and a view to a patio area.

8. Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!

Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!
Kannapali Beach Area
10.0 out of 10, Exceptional, (205 reviews)
"This condo was perfect for my family of 4! It was the perfect location. We have been to this resort the last 5 years and this is by far the best place. The owners are easy to get a hold off and graciously let us extend our trip 1 day due to a delay. Thank you for allowing us to stay in your lovely place. We hope to return next year!"
United States
Lori T.
The price is CA $243
CA $858 total
includes taxes & fees
Oct 16 - Oct 17
Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!
A swimming pool with lounge chairs and palm trees in the background.

9. Summertime Special Prices!! Book Now!

Summertime Special Prices!! Book Now!
Kannapali Beach Area
10.0 out of 10, Exceptional, (175 reviews)
"Great condo! Super close to parking, beach access, and pool area. Area was pretty central to all of the excursions we took, so it worked out great. Close walk to the beach walk to watch the sunset each night. Overall a great trip!"
United States
Rhonda R.
The price is CA $243
CA $858 total
includes taxes & fees
Oct 30 - Oct 31
Summertime Special Prices!! Book Now!
A beach view with palm trees, a clear sky, and a distant mountain.

10. The Whaler 518 – Remodeled Ocean View Studio on Kāʻanapali Beach

The Whaler 518 – Remodeled Ocean View Studio on Kāʻanapali Beach
Kannapali Beach Area
9.6 out of 10, Exceptional, (81 reviews)
"Good view, good location!"
United States
Nate M.
The price is CA $314
CA $1,339 total
includes taxes & fees
Oct 16 - Oct 17
The Whaler 518 – Remodeled Ocean View Studio on Kāʻanapali Beach
A large outdoor swimming pool with a rock feature, surrounded by palm trees and lounge chairs.

11. Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742

Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742
Lahaina
8.8 out of 10, Excellent, (114 reviews)
"Great location Clean Room Great property"
United States
Robert T.
The price is CA $139
CA $1,092 total
includes taxes & fees
Oct 24 - Oct 25
Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742
A pool area with a waterfall, stone steps, and tropical plants.

12. Charming 1BR Condo at Oceanfront Kaanapali Shores Unit 422

Charming 1BR Condo at Oceanfront Kaanapali Shores Unit 422
Lahaina
7.8 out of 10, Good, (92 reviews)
"we had a wonderful time. the best vrbo we have stayed in. everything was perfect."
United States
jane r.
The price is CA $139
CA $1,123 total
includes taxes & fees
Oct 26 - Oct 27
Charming 1BR Condo at Oceanfront Kaanapali Shores Unit 422
A round table with a bottle, a glass, a loaf of bread, grapes, and a vase with flowers.

13. Hawaiiana Suite for 3, Private Beach Club, walk Kaanapali Beach, Gym

Hawaiiana Suite for 3, Private Beach Club, walk Kaanapali Beach, Gym
Kannapali Beach Area
9.0 out of 10, Wonderful, (45 reviews)
"Air conditioning was great. Room was very clean and easy check in process. We only stayed 2 nights here but it would have worked perfectly for extended stays as well! "
United States
Stephanie S.
The price is CA $249
CA $712 total
includes taxes & fees
Oct 28 - Oct 29
Hawaiiana Suite for 3, Private Beach Club, walk Kaanapali Beach, Gym
A resort with a pool, palm trees, and a building with balconies.

14. Oceanview - Papakea H107 AC, King Bed, Ground Corner Unit

Oceanview - Papakea H107 AC, King Bed, Ground Corner Unit
Lahaina
10.0 out of 10, Exceptional, (31 reviews)
"Great condo would highly recommend it. Great location and the resort is very well maintained. Got to see whales from the shoreline. "
United States
Mitchell M.
The price is CA $165
CA $1,158 total
includes taxes & fees
Oct 17 - Oct 18
Oceanview - Papakea H107 AC, King Bed, Ground Corner Unit
A resort with a pool, palm trees, a waterfall, and a view of the ocean.

15. The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas
4.0 star property
Kannapali Beach Area
8.6 out of 10, Excellent, (1,169 reviews)
"The facilities were exactly as described. Our ocean front room and the hotel amenities were wonderful."
Canada
James
The price is CA $590
CA $701 total
includes taxes & fees
Oct 27 - Oct 28
The Westin Ka'anapali Ocean Resort Villas
Million dollar view of the beach drone shot

16. Spacious Studio w AC Pool and Beach Cabana - Maui Eldorado J209

Spacious Studio w AC Pool and Beach Cabana - Maui Eldorado J209
Kannapali Beach Area
9.0 out of 10, Wonderful, (45 reviews)
"We love staying at the Maui Eldorado and J209 was perfect for us. The unit was quiet and had everything we needed for a comfortable, relaxing vacation. We even received a call from property manager just making sure we had a nice stay. "
United States
Mark H.
The price is CA $398
CA $1,009 total
includes taxes & fees
Oct 19 - Oct 20
Spacious Studio w AC Pool and Beach Cabana - Maui Eldorado J209
A resort with a pool, palm trees, and a night scene with fire torches.

17. Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
4.0 star property
Kannapali Beach Area
8.6 out of 10, Excellent, (257 reviews)
"Our 2-bedroom was on the top floor with beautiful ocean views. The 3-bathrooms made it so nice for our group to each have one. The complimentary shuttles to Whaler’s Village made getting around a breeze. This location cannot be beat on Maui!"
United States
Lisa
The price is CA $727
CA $863 total
includes taxes & fees
Oct 29 - Oct 30
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Beach

18. Beachfront clubhouse, new furnishings, 1st floor, bonus 2 bathroom

Beachfront clubhouse, new furnishings, 1st floor, bonus 2 bathroom
Kannapali Beach Area
9.8 out of 10, Exceptional, (18 reviews)
"Loved the location and amenities. Golf cart rides to the cabana and best beach were a major plus for us. Only wish there was a restaurant on the premises. Will return again!"
United States
Peggy V.
The price is CA $320
CA $950 total
includes taxes & fees
Nov 7 - Nov 8
Beachfront clubhouse, new furnishings, 1st floor, bonus 2 bathroom
Lobby

19. Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.2 out of 10, Wonderful, (1,566 reviews)
"Great location, very nice condo, pool, and beach access."
United States
Stewart
The price is CA $499
CA $887 total
includes taxes & fees
Oct 26 - Oct 27
Aston at The Whaler on Kaanapali Beach
A balcony with a table and two chairs, overlooking a body of water with a distant landmass.

20. BeachFront: MauiKai - WestMaui, Hawaii

BeachFront: MauiKai - WestMaui, Hawaii
Lahaina
9.2 out of 10, Wonderful, (44 reviews)
"Loved our stay! The view was incredible and saw many whales, seals and turtles. Check in was easy and great communication with the owner. "
Canada
carla h.
The price is CA $178
CA $656 total
includes taxes & fees
Oct 27 - Oct 28
BeachFront: MauiKai - WestMaui, Hawaii
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kaanapali Hotel Reviews

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

10/10 Excellent
"We had an amazing time during our honey moon and loved how close we were to everything. We were walking distance to all the dinners we planned and didn’t even know it! This area was the best and can’t wait to come back :)"
Derric Jaymes 6-night trip
Posted 2 hours ago
OUTRIGGER Kaanapali Beach Resort

Price trends for vacation rentals in Kaanapali

Less expensive
More expensive
Next month
August
March
CA $310
Month
Price
January
CA $401
February
CA $425
March
CA $446
April
CA $379
May
CA $328
June
CA $289
July
CA $312
August
CA $263
September
CA $273
October
CA $311
November
CA $310
December
CA $389
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Kaanapali. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Kaanapali

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Kaanapali. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Kaanapali?

Yes, we have vacation rentals near popular sights in Kaanapali, or you can choose a more secluded option if you want a relaxing place to stay. Tourists who visit Kaanapali speak highly of the array of shops and relaxing spas. Make sure to also enjoy the popular beaches and top-notch restaurants during your vacation.

What are some of the best vacation rentals that Kaanapali has to offer?

#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool: This Kaanapali vacation home rental is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 11 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. Our travelers also rate The Best of the Best JUST GOT BETTER with 3rd Remodel as a favorite home for rent in Kaanapali.

How many vacation rentals are there in Kaanapali?

With 24 Expedia vacation rentals, you're sure to find just the right place for your Kaanapali stay.

What can I see and do in Kaanapali?

Kaanapali Beach and Kahekili Beach are a couple of great spots to enjoy nature, whereas other top attractions include Whalers Village. Black Rock and Kaanapali Kai Course at Kaanapali Golf Resort are other places to visit while you're in town.

What are vacation rentals like in Kaanapali?

Vacation rentals are private properties you can stay in for several days or more in Kaanapali. Vacation rentals feature amenities like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for family trips.