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Kaanapali Hillside Vacation Rentals

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Our top choices for Kaanapali Hillside vacation rentals

1. Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach
4.0 star property
Lahaina
9.2 out of 10, Wonderful, (1,553 reviews)
"Lovely place with full amenities and walk out patio in the lawn. Would definitely book again!"
United States
Heidi
The price is CA $245
CA $824 total
includes taxes & fees
Aug 20 - Aug 21
Aston at The Whaler on Kaanapali Beach

2. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,607 reviews)
"Great location and friendly staff"
Canada
Daniel
The price is CA $324
CA $509 total
includes taxes & fees
Sep 1 - Sep 2
Aston Maui Kaanapali Villas

3. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (445 reviews)
"Amazing views and location. Great employees."
United States
Ramon
The price is CA $317
CA $886 total
includes taxes & fees
Aug 10 - Aug 11
The Whaler Resort Kaanapali Beach

4. Beautiful Ocean and Outer Island Views! See Whales in season!

Beautiful Ocean and Outer Island Views! See Whales in season!
Lahaina
9.4 out of 10, Exceptional, (90 reviews)
"Overall a 4/5 experience! I would stay here again without a doubt. Simple check-in process, attentive host, great ocean views, and a well equipped condo. The only drawback I can think of was in regards to some of the aging furnishings. "
United States
Timo S.
The price is CA $130
CA $548 total
includes taxes & fees
Aug 14 - Aug 15
Beautiful Ocean and Outer Island Views! See Whales in season!

5. Top Floor, Corner Unit, Pool View, Kaanapali Beach

Top Floor, Corner Unit, Pool View, Kaanapali Beach
Kaanapali
9.4 out of 10, Exceptional, (61 reviews)
"Everything about stay was wonderfulCentrally located , easy to get to from airportStudio room perfect for our needs. Close to pool and rides to beach made it easy Thank you for a great stay "
United States
Terri B.
The price is CA $202
CA $639 total
includes taxes & fees
Aug 26 - Aug 27
Top Floor, Corner Unit, Pool View, Kaanapali Beach

6. Kuleana Club - 504

Kuleana Club - 504
3.5 star property
Lahaina
8.0 out of 10, Very good, (1 review)
The price is CA $190
CA $515 total
includes taxes & fees
Aug 13 - Aug 14
Kuleana Club - 504

7. 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, (108 reviews)
"Lovely room in a great location. Check in and check out were super easy, great amenities"
United States
Michaela F.
The price is CA $159
CA $1,087 total
includes taxes & fees
Aug 10 - Aug 11
Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

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

Renovated Studio Ka’anapali Shores | Pools, AC, Beach Access
lahaina
9.6 out of 10, Exceptional, (20 reviews)
"It was a great resort We will be back for sure"
United States
Gregory M.
The price is CA $159
CA $1,103 total
includes taxes & fees
Aug 13 - Aug 14
Renovated Studio Ka’anapali Shores | Pools, AC, Beach Access

9. Kāʻanapali Ocean View Condo with Beachfront Cabana for Guests

Kāʻanapali Ocean View Condo with Beachfront Cabana for Guests
Lahaina
10.0 out of 10, Exceptional, (169 reviews)
"Fantastic room. Always clean and well stocked.Host is wonderful to work with.Our favorite place to visit."
United States
Wayne W.
The price is CA $279
CA $703 total
includes taxes & fees
Aug 22 - Aug 23
Kāʻanapali Ocean View Condo with Beachfront Cabana for Guests

10. Summertime Special Prices!! Book Now!

Summertime Special Prices!! Book Now!
Lahaina
10.0 out of 10, Exceptional, (169 reviews)
"Very nicely decorated, clean, spacious, close to beach"
United States
Sandra L.
The price is CA $238
CA $832 total
includes taxes & fees
Aug 10 - Aug 11
Summertime Special Prices!! Book Now!

11. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,243 reviews)
"Great location, good value for the money."
United States
ANGELO
The price is CA $325
CA $427 total
includes taxes & fees
Aug 14 - Aug 15
Aston Kaanapali Shores

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

Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!
Lahaina
10.0 out of 10, Exceptional, (203 reviews)
"We loved our room!! The shower and bed were our highlights for sure. Definitely recommend staying here!!"
United States
Emily A.
The price is CA $245
CA $846 total
includes taxes & fees
Aug 12 - Aug 13
Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!

13. 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, (113 reviews)
"Great location Clean Room Great property"
United States
Robert T.
The price is CA $159
CA $1,087 total
includes taxes & fees
Aug 11 - Aug 12
Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742

14. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,846 reviews)
"The room was clean and the beach views and access to the beach was beyond beautiful. A really cozy place to stay."
United States
Jesus
The price is CA $320
CA $380 total
includes taxes & fees
Aug 23 - Aug 24
Napili Shores Maui by OUTRIGGER

15. Ocean View, Kaanapali Golf Course front, Beach Cabana

Ocean View, Kaanapali Golf Course front, Beach Cabana
Kaanapali
9.8 out of 10, Exceptional, (54 reviews)
"Great location. The condo was immaculate and they thought of everything you might need. I would definitely recommend and stay there again."
United States
Patti A.
The price is CA $236
CA $683 total
includes taxes & fees
Aug 28 - Aug 29
Ocean View, Kaanapali Golf Course front, Beach Cabana

16. The best spot for whale watching!

The best spot for whale watching!
Lahaina
9.8 out of 10, Exceptional, (150 reviews)
"The view is amazing! "
United States
Alyssa F.
The price is CA $187
CA $562 total
includes taxes & fees
Aug 11 - Aug 12
The best spot for whale watching!

17. Kaanapali Golf course front, Beach cabana, Jacuzzi

Kaanapali Golf course front, Beach cabana, Jacuzzi
Kaanapali
9.6 out of 10, Exceptional, (53 reviews)
"Loved this unit, we have stayed many times at Maui Eldorado with different family members renting different units. This was definitely one of the nicest, location was great,quiet, very clean and very well stocked, with a nice modern kitchen - compared to another unit we had also rented on this visit. Would definitely rent it again if it is available "
United States
Patricia H.
Kaanapali Golf course front, Beach cabana, Jacuzzi

18. Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!

Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!
Lahaina
9.8 out of 10, Exceptional, (274 reviews)
"Amazing trip!"
United States
Eric L.
The price is CA $188
CA $669 total
includes taxes & fees
Aug 13 - Aug 14
Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!

19. OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (3,014 reviews)
"Great place to stay especially if it’s your first time!"
United States
Jessica
The price is CA $506
CA $1,244 total
includes taxes & fees
Aug 20 - Aug 21
OUTRIGGER Honua Kai Resort & Spa

20. FANTASTIC OCEAN VIEW, LUSH GARDENS, QUIET REMODELED END UNIT, 2 KING BEDS, A/C

FANTASTIC OCEAN VIEW, LUSH GARDENS, QUIET REMODELED END UNIT, 2 KING BEDS, A/C
Lahaina
9.8 out of 10, Exceptional, (181 reviews)
"Property was clean, well supplied and convenient location for all our activities on Maui. Communication was excellent with the owners when we had any questions. Would definitely stay here again!! Even got to see a rainbow while sitting on our Lani."
United States
Marisa M.
The price is CA $375
CA $1,513 total
includes taxes & fees
Aug 18 - Aug 19
FANTASTIC OCEAN VIEW, LUSH GARDENS, QUIET REMODELED END UNIT, 2 KING BEDS, A/C
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.
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Top Kaanapali Hillside Hotel Reviews

Find out more about Kaanapali Hillside

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 Hillside. 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.

Frequently asked questions

Can I find a vacation rental in Kaanapali Hillside?

Yes, we have vacation rentals near well known sights in Kaanapali Hillside, or you can select a more secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Kaanapali Hillside?

Kapalua Golf Villas Resort by KBM: You might want to consider this vacation home rental near Kaanapali Hillside, which is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, an oven, and a microwave. Kick off your shoes and enjoy yourself with a terrace and a garden.

What’s there to see and do in Kaanapali Hillside?

Explore the area and family-friendly sights such as Hawaii Nature Center of Iao Valley, or get out into nature at a spot like Kaanapali Beach. Whalers Village and Napili Bay are other popular places to visit in the area.

What’s a vacation rental in Kaanapali Hillside like?

A vacation rental is a private property you can book for a long or short time in Kaanapali Hillside. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.