Kaanapali Hillside Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Kaanapali Hillside vacation rentals

Garden

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,051 reviews)
"Beautiful location and friendly helpful staff. Nice clean rooms and resort. "
Canada
Megan Ruth
The price is ￥50,695
￥64,899 total
includes taxes & fees
Apr 16 - Apr 17
Aston Kaanapali Shores
Beach nearby, white sand, beach towels

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (176 reviews)
"Great location "
United States
John Roger
The price is ￥30,470
￥36,171 total
includes taxes & fees
Apr 22 - Apr 23
Napili Village Hotel
On the beach

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,783 reviews)
"Ocean view, comfortable room, nice bar on property, well located"
United States
Rosanne Marie
The price is ￥39,285
￥46,636 total
includes taxes & fees
Apr 19 - Apr 20
Napili Shores Maui by OUTRIGGER
Beach

Unit 24 Waena Inn - Maui Private Suite

Unit 24 Waena Inn - Maui Private Suite
Wailuku
9.6 out of 10, Exceptional, (17 reviews)
"Excellent location, assigned parking"
United States
Virinchi Roy S.
The price is ￥41,416
￥57,947 total
includes taxes & fees
May 3 - May 4
Unit 24 Waena Inn - Maui Private Suite
Beachfront Two Bedrooms | In-room safe, iron/ironing board, free WiFi, bed sheets

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (654 reviews)
"Clean room amd friendly staff."
United States
Chris
The price is ￥44,684
￥53,046 total
includes taxes & fees
Apr 11 - Apr 12
Napili Sunset on the Beach
Suite, Multiple Beds, Garden View (2 Baths) | Garden view

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (378 reviews)
"Beautiful views, wonderful staff, clean & spacious room! Would love to stay again someday. "
United States
Sophia
The price is ￥58,069
￥127,000 total
includes taxes & fees
Apr 12 - Apr 13
The Whaler Resort Kaanapali Beach
2 outdoor pools

Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,557 reviews)
"Best Maui location"
United States
Chris
The price is ￥50,060
￥73,572 total
includes taxes & fees
Apr 12 - Apr 13
Aston Maui Kaanapali Villas
Property grounds

Bright, Beautiful, Remodeled Island Sands 505 Condo

Bright, Beautiful, Remodeled Island Sands 505 Condo
Wailuku
9.4 out of 10, Exceptional, (57 reviews)
"Stay was great, condo was well equipped, great location and beautiful view."
United States
Tara C.
The price is ￥40,207
￥149,817 total
includes taxes & fees
Apr 13 - Apr 14
Bright, Beautiful, Remodeled Island Sands 505 Condo
On the beach

Romantic Beachfront Getaway

Romantic Beachfront Getaway
Maalaea Bay
9.6 out of 10, Exceptional, (43 reviews)
"Excellent location. "
United States
Thomas
The price is ￥29,400
￥75,571 total
includes taxes & fees
Apr 9 - Apr 10
Romantic Beachfront Getaway
Outdoor dining

OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
Wailuku
9.6 out of 10, Exceptional, (167 reviews)
"Great location on the island, nice accommodations. "
United States
Chris P.
The price is ￥15,733
￥55,463 total
includes taxes & fees
Apr 11 - Apr 12
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
Beach

Unit 23 Waena Inn - Maui Private Suite

Unit 23 Waena Inn - Maui Private Suite
Wailuku
10.0 out of 10, Exceptional, (10 reviews)
"Fairly central location. Helpful and due to the length of our stay, offered for us to use washer/dryer, snorkels, beach towels. "
United States
Suzan F.
The price is ￥35,743
￥53,148 total
includes taxes & fees
Apr 9 - Apr 10
Unit 23 Waena Inn - Maui Private Suite
On the beach

Oceanside condo, full kitchen, ocean view. Fully renovated 2023

Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Central Kihei
9.4 out of 10, Exceptional, (67 reviews)
"The room was perfect! "
United States
Gillian
The price is ￥20,024
￥58,726 total
includes taxes & fees
Apr 15 - Apr 16
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
4 outdoor pools, open 8:00 AM to 10:00 PM, cabanas (surcharge)

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (2,945 reviews)
"Nice staff/clean rooms. Overall very nice"
Canada
Anastassiya
The price is ￥45,320
￥127,139 total
includes taxes & fees
Apr 22 - Apr 23
OUTRIGGER Honua Kai Resort & Spa
Smart TV, DVD player, books, streaming services

This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!

This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!
North Kihei
10.0 out of 10, Exceptional, (39 reviews)
"we really enjoyed our stay here. It is clean and maintained well and close to the beach."
United States
stuti s.
The price is ￥22,090
￥74,394 total
includes taxes & fees
Apr 10 - Apr 11
This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!
On the beach, sun loungers, beach towels

Sugar Beach Resort Oceanview 1 bed/1 bath

Sugar Beach Resort Oceanview 1 bed/1 bath
North Kihei
9.6 out of 10, Exceptional, (117 reviews)
"Condo is fully stocked and decorated beautifully! "
United States
erin t.
The price is ￥25,745
￥71,565 total
includes taxes & fees
Apr 13 - Apr 14
Sugar Beach Resort Oceanview 1 bed/1 bath
Outdoor dining

Oceanfront condo with pool & balcony - walk to dining, activities, and more

Oceanfront condo with pool & balcony - walk to dining, activities, and more
Wailuku
9.4 out of 10, Exceptional, (132 reviews)
"Beautiful view!!"
United States
Gene E.
The price is ￥26,699
￥103,980 total
includes taxes & fees
Apr 15 - Apr 16
Oceanfront condo with pool & balcony - walk to dining, activities, and more
Sun loungers

Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

Ocean View 2-bedroom condo with pool and AC in wonderful Kihei
North Kihei
9.8 out of 10, Exceptional, (26 reviews)
"Nice place"
Canada
PC SHOP
The price is ￥25,602
￥75,778 total
includes taxes & fees
Apr 9 - Apr 10
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei
On the beach

Direct Beachfront Newly Remodeled!

Direct Beachfront Newly Remodeled!
North Kihei
9.2 out of 10, Wonderful, (28 reviews)
"Very nice right on the beach "
United States
MATILDA
The price is ￥52,490
￥65,410 total
includes taxes & fees
Apr 30 - May 1
Direct Beachfront Newly Remodeled!
Terrace/patio

SUMMER SPECIAL!!! OWNER HOST DIRECT OCEAN FRONT Longest Sandy Beach on Maui

SUMMER SPECIAL!!! OWNER HOST DIRECT OCEAN FRONT Longest Sandy Beach on Maui
North Kihei
10.0 out of 10, Exceptional, (145 reviews)
"Our host was so responsive, kind and helpful! "
United States
Laura C.
The price is ￥39,333
￥93,967 total
includes taxes & fees
Apr 15 - Apr 16
SUMMER SPECIAL!!! OWNER HOST DIRECT OCEAN FRONT Longest Sandy Beach on Maui
Property grounds

The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas
4.0 star property
Lahaina
8.6 out of 10, Excellent, (1,133 reviews)
"Staff friendly, great room and cleanliness. Amenties were excellent. "
United States
WILLIAM
The price is ￥72,309
￥85,837 total
includes taxes & fees
Apr 14 - Apr 15
The Westin Ka'anapali Ocean Resort Villas
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

Hilton Vacation Club Ka'anapali Beach Maui

Hilton Vacation Club Ka'anapali Beach Maui

4/10 Poor
"Outdated"
Julee 1-night trip
Posted 3 hours ago
Hilton Vacation Club Ka'anapali Beach Maui

Find out more about Kaanapali Hillside

Search for holiday rentals in Kaanapali Hillside on Expedia! You can easily find your home rentals, villas, holiday apartments in Kaanapali Hillside using one of the methods below:

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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?

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32: Visitors like this Kaanapali Hillside vacation home rental. It 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. 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. You can relax into your vacation with a garden and a selection of games.

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 Kaanapali Kai Course at Kaanapali Golf Resort are a couple of places you'll find in the larger 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.