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Kaanapali Hillside Holiday Rentals

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Our top choices for Kaanapali Hillside holiday rentals

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$1,400
includes taxes & fees
11 July - 12 July
Bright, Beautiful, Remodeled Island Sands 505 Condo

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, (172 reviews)
"Nice place and conviently located"
United States
Mike M.
The price is NZ$651
includes taxes & fees
12 July - 13 July
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$844
includes taxes & fees
10 July - 11 July
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

The Napili Bay, Steps to Sand, Studio, King bed, Remodeled in June of 2023

The Napili Bay, Steps to Sand, Studio, King bed, Remodeled in June of 2023
Lahaina
10.0 out of 10, Exceptional, (40 reviews)
"The host is always very accommodating and nice. The condo is very nice. We love staying there. "
United States
John D.
The price is NZ$630
includes taxes & fees
14 July - 15 July
The Napili Bay, Steps to Sand, Studio, King bed, Remodeled in June of 2023

Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly
North Kihei
9.0 out of 10, Wonderful, (10 reviews)
"Great stay, clean place. Close walk to the beach. The pool and hot tub were great and well taken care of"
United States
Danniella
The price is NZ$698
includes taxes & fees
12 July - 13 July
Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

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
9.8 out of 10, Exceptional, (303 reviews)
"Exceptional host, comfy beds and pillows, great location!"
United States
Brenda C.
The price is NZ$720
includes taxes & fees
15 July - 16 July
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

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, (42 reviews)
"Had lots of great and useful amenities "
United States
Rochelle P.
The price is NZ$779
includes taxes & fees
9 July - 10 July
Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

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
9.8 out of 10, Exceptional, (279 reviews)
"Absolutely perfect stay! Kevin was very kind and very communicative. I highly recommend staying here when visiting Kīhei."
United States
Sylvia
The price is NZ$720
includes taxes & fees
14 July - 15 July
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

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$1,031
includes taxes & fees
9 July - 10 July
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$511
includes taxes & fees
9 July - 10 July
Unit 23 Waena Inn - Maui Private Suite

Unit 25 Waena Inn - Maui Private Suite

Unit 25 Waena Inn - Maui Private Suite
Wailuku
9.8 out of 10, Exceptional, (16 reviews)
"Great place "
United States
Noah S.
The price is NZ$506
includes taxes & fees
12 July - 13 July
Unit 25 Waena Inn - Maui Private Suite

Sugar Beach Resort Oceanview 1 bed/1 bath

Sugar Beach Resort Oceanview 1 bed/1 bath
North Kihei
9.6 out of 10, Exceptional, (118 reviews)
"Great location, great property and great condo. "
Canada
DIANNE V.
The price is NZ$803
includes taxes & fees
10 July - 11 July
Sugar Beach Resort Oceanview 1 bed/1 bath

New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.

New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.
North Kihei
9.6 out of 10, Exceptional, (16 reviews)
"Perfect ocean views for morning coffee. Close to all the restaurants and good beaches "
United States
Michael A.
The price is NZ$746
includes taxes & fees
13 July - 14 July
New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.

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, (31 reviews)
"Beach view and very clean. Happy with our stay. "
United States
Shannon T.
The price is NZ$810
includes taxes & fees
9 July - 10 July
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

🤙 June-July-August SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE

🤙 June-July-August SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE
North Kihei
10.0 out of 10, Exceptional, (142 reviews)
"This is the perfect getaway spot. Great direct view of the ocean and beach. "
United States
Mike H.
The price is NZ$1,129
includes taxes & fees
14 July - 15 July
🤙 June-July-August SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE

Steps to the Beach, Affordable w/Free Parking

Steps to the Beach, Affordable w/Free Parking
North Kihei
9.6 out of 10, Exceptional, (171 reviews)
"Clean, across the street from beach and whale center. Great location to get to other places on the island. "
Canada
wayneiversonphotosk
The price is NZ$763
includes taxes & fees
12 July - 13 July
Steps to the Beach, Affordable w/Free Parking

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, (78 reviews)
"We loved our stay! Great location"
United States
Madison
The price is NZ$600
includes taxes & fees
22 July - 23 July
Oceanside condo, full kitchen, ocean view. Fully renovated 2023

OCEANFRONT RESORT-CHECK OUT OUR WINTER RATES! Kihei Sands Beachfrnt Condo B14

OCEANFRONT RESORT-CHECK OUT OUR WINTER RATES! Kihei Sands Beachfrnt Condo B14
North Kihei
9.8 out of 10, Exceptional, (105 reviews)
"Great location. Staff was outstanding. The condo was as advertised and we were very impressed with how spotless everything was."
United States
Gary R.
The price is NZ$1,192
includes taxes & fees
21 July - 22 July
OCEANFRONT RESORT-CHECK OUT OUR WINTER RATES! Kihei Sands Beachfrnt Condo B14

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, (310 reviews)
"Parking was fine, was in contact with Kevin about the status of the complex due to the Kona rains. Nice unit for our stay. Bed was comfortable, kitchen worked well for the food prep that we needed. "
United States
Kathryn M.
The price is NZ$718
includes taxes & fees
12 July - 13 July
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

Top Floor Beachfront Condo with Ocean view

Top Floor Beachfront Condo with Ocean view
North Kihei
9.6 out of 10, Exceptional, (57 reviews)
"Central location and helpful site manager "
United States
Richard W.
The price is NZ$896
includes taxes & fees
16 July - 17 July
Top Floor Beachfront Condo with Ocean view
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$517 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?

Stunning Views & Tropical Tranquility 429 LS: This holiday home rental outside of Kaanapali Hillside is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

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 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.