Kaanapali Hillside Holiday Rentals

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Our top choices for Kaanapali Hillside holiday rentals

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, (170 reviews)
"Great location on the island, nice accommodations. "
United States
Chris P.
The price is NZ$571
includes taxes & fees
26 May - 27 May
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
North Kihei
9.8 out of 10, Exceptional, (109 reviews)
"This place was in a good location in Kihei. You are within 5 mins of dozen of beaches. All the beach gear a person needs is provided(towels, chairs, snorkels, flippers, coolers and more)! Jon is super friendly and a great host!"
United States
Troy s.
The price is NZ$819
includes taxes & fees
25 May - 26 May
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View
North Kihei
10.0 out of 10, Exceptional, (40 reviews)
"Had lots of great and useful amenities "
United States
Rochelle P.
The price is NZ$733
includes taxes & fees
25 May - 26 May
Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

Warm Winter Getaway w/ a View - BEACHFRONT PROPERTY A13 at Kihei Sands

Warm Winter Getaway w/ a View - BEACHFRONT PROPERTY A13 at Kihei Sands
North Kihei
9.8 out of 10, Exceptional, (72 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: It was an amazing stay and a great place! I will be back!"
United States
Lauree M.
The price is NZ$989
includes taxes & fees
25 May - 26 May
Warm Winter Getaway w/ a View - BEACHFRONT PROPERTY A13 at Kihei Sands

Unit 23 Waena Inn - Maui Private Suite

Unit 23 Waena Inn - Maui Private Suite
Wailuku
10.0 out of 10, Exceptional, (11 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 NZ$527
includes taxes & fees
30 May - 31 May
Unit 23 Waena Inn - Maui Private Suite

Simply Amazing Oceanfront Condo! Milowai 310

Simply Amazing Oceanfront Condo! Milowai 310
Wailuku
10.0 out of 10, Exceptional, (21 reviews)
"Very good location and amenities. "
United States
Jiaxing B.
The price is NZ$902
includes taxes & fees
4 June - 5 June
Simply Amazing Oceanfront Condo! Milowai 310

Top Floor Beachfront Condo with Ocean view

Top Floor Beachfront Condo with Ocean view
North Kihei
9.8 out of 10, Exceptional, (54 reviews)
"Central location and helpful site manager "
United States
Richard W.
The price is NZ$879
includes taxes & fees
25 May - 26 May
Top Floor Beachfront Condo with Ocean view

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, (73 reviews)
"Great place and hospitality "
United States
Yash P.
The price is NZ$605
includes taxes & fees
31 May - 1 June
Oceanside condo, full kitchen, ocean view. Fully renovated 2023

Bright, Beautiful, Remodeled Island Sands 505 Condo

Bright, Beautiful, Remodeled Island Sands 505 Condo
Wailuku
9.4 out of 10, Exceptional, (58 reviews)
"The property was very clean and well maintained! We enjoyed our stay. "
United States
Cindy B.
The price is NZ$1,450
includes taxes & fees
7 June - 8 June
Bright, Beautiful, Remodeled Island Sands 505 Condo

Romantic Beachfront Getaway

Romantic Beachfront Getaway
Maalaea Bay
9.6 out of 10, Exceptional, (43 reviews)
"Excellent location. "
United States
Thomas
The price is NZ$815
includes taxes & fees
25 May - 26 May
Romantic Beachfront Getaway

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
10.0 out of 10, Exceptional, (274 reviews)
"Perfectly situated on Maui island to easily visit everything and come back to condo to sleep."
Canada
Jean-Philippe R.
The price is NZ$710
includes taxes & fees
16 June - 17 June
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
North Kihei
10.0 out of 10, Exceptional, (308 reviews)
"Great place, easy access and parking. Host communication was exceptional, would not hesitate to rent again."
United States
M P.
The price is NZ$710
includes taxes & fees
27 May - 28 May
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

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 NZ$781
includes taxes & fees
1 June - 2 June
Sugar Beach Resort Oceanview 1 bed/1 bath

Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!

Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!
North Kihei
9.8 out of 10, Exceptional, (208 reviews)
"Gorgeous condo right on the beach! Zero complaints! Thank you for sharing your home."
United States
Susan C.
The price is NZ$806
includes taxes & fees
25 May - 26 May
Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!

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, (28 reviews)
"Nice place"
Canada
PC SHOP
The price is NZ$797
includes taxes & fees
25 May - 26 May
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

Sugar Beach 102 Gorgeous Remodeled Home Beachfront Condo Home

Sugar Beach 102 Gorgeous Remodeled Home Beachfront Condo Home
North Kihei
9.4 out of 10, Exceptional, (44 reviews)
"The pool and hot tub are great and very easy to access. The views are stunning. And the grounds are kept incredibly clean and groomed. "
United States
Guy C.
The price is NZ$961
includes taxes & fees
8 June - 9 June
Sugar Beach 102 Gorgeous Remodeled Home Beachfront Condo Home

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 NZ$1,101
includes taxes & fees
5 June - 6 June
Oceanfront condo with pool & balcony - walk to dining, activities, and more

Updated Napili Shores Studio King Bed A/C Walk to Napili Bay

Updated Napili Shores Studio King Bed A/C Walk to Napili Bay
Lahaina
9.8 out of 10, Exceptional, (149 reviews)
"Good communication, great location, comfortable bed and convenient layout "
United States
Aliyah K.
The price is NZ$636
includes taxes & fees
25 May - 26 May
Updated Napili Shores Studio King Bed A/C Walk to Napili Bay

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (183 reviews)
"The property is beautiful and located just steps away from the beach."
United States
Patricia
The price is NZ$337
includes taxes & fees
29 May - 30 May
Napili Village Hotel

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, (271 reviews)
"enjoyed our stay "
United States
Alicia H.
The price is NZ$800
includes taxes & fees
4 June - 5 June
Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!
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

Everything you need to know about Kaanapali Hillside holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kaanapali Hillside holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kaanapali Hillside holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Kaanapali Hillside holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kaanapali Hillside. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kaanapali Hillside holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kaanapali Hillside holiday rentals we have selected for you start as low as NZ$481 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kaanapali Hillside rentals

At Expedia, we put the best Kaanapali Hillside holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Kaanapali Hillside rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kaanapali Hillside holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kaanapali Hillside. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Kaanapali Hillside?

Yes, there are holiday rentals close to the most popular sights in Kaanapali Hillside, or you can select a more secluded option if you're looking for a relaxing stay.

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

Kapalua Golf Villas Resort by KBM: This holiday home rental outside of Kaanapali Hillside is located on the beach, and has an outdoor pool, a balcony and a BBQ 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 Kahekili Beach are a couple of places you'll find in the wider area.

What’s a holiday rental in Kaanapali Hillside like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kaanapali Hillside. Holiday rentals feature amenities like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for family gatherings.