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Kaanapali Hillside Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Kaanapali Hillside vacation rentals

Property grounds

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 ￥26,857
￥132,678 total
includes taxes & fees
Jul 12 - Jul 13
Bright, Beautiful, Remodeled Island Sands 505 Condo
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, (172 reviews)
"Nice place and conviently located"
United States
Mike M.
The price is ￥29,030
￥74,380 total
includes taxes & fees
Jul 21 - Jul 22
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
Sun loungers, beach towels

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 ￥14,147
￥78,520 total
includes taxes & fees
Jul 11 - Jul 12
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
On the beach, sun loungers, beach towels

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 ￥18,814
￥59,223 total
includes taxes & fees
Jul 14 - Jul 15
The Napili Bay, Steps to Sand, Studio, King bed, Remodeled in June of 2023
Free WiFi, bed sheets

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 ￥17,826
￥64,906 total
includes taxes & fees
Jul 12 - Jul 13
Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly
Outdoor dining

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)
The price is ￥18,320
￥66,726 total
includes taxes & fees
Aug 1 - Aug 2
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
Smart TV, DVD player, books, streaming services

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 ￥18,489
￥73,249 total
includes taxes & fees
Jul 9 - Jul 10
Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View
Outdoor dining

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 ￥18,320
￥66,726 total
includes taxes & fees
Jul 15 - Jul 16
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
On the beach

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 ￥30,627
￥97,356 total
includes taxes & fees
Jul 10 - Jul 11
Warm Winter Getaway w/ a View - BEACHFRONT PROPERTY A13 at Kihei Sands
Beach

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 ￥32,068
￥47,579 total
includes taxes & fees
Jul 9 - Jul 10
Unit 23 Waena Inn - Maui Private Suite
Interior

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 ￥31,794
￥47,305 total
includes taxes & fees
Jul 12 - Jul 13
Unit 25 Waena Inn - Maui Private Suite
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, (118 reviews)
"Great location, great property and great condo. "
Canada
DIANNE V.
The price is ￥27,441
￥74,590 total
includes taxes & fees
Jul 10 - Jul 11
Sugar Beach Resort Oceanview 1 bed/1 bath
On the beach, sun loungers, beach towels

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 ￥20,029
￥68,793 total
includes taxes & fees
Jul 9 - Jul 10
New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.
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, (31 reviews)
"Beach view and very clean. Happy with our stay. "
United States
Shannon T.
The price is ￥24,648
￥75,878 total
includes taxes & fees
Jul 9 - Jul 10
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei
Outdoor dining

🤙 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 ￥38,487
￥104,192 total
includes taxes & fees
Jul 16 - Jul 17
🤙 June-July-August SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE
On the beach, sun loungers, beach towels

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 ￥18,975
￥70,939 total
includes taxes & fees
Jul 12 - Jul 13
Steps to the Beach, Affordable w/Free Parking
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, (78 reviews)
"We loved our stay! Great location"
United States
Madison
The price is ￥17,807
￥56,300 total
includes taxes & fees
Jul 22 - Jul 23
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
On the beach

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 ￥35,517
￥109,212 total
includes taxes & fees
Jul 9 - Jul 10
OCEANFRONT RESORT-CHECK OUT OUR WINTER RATES! Kihei Sands Beachfrnt Condo B14
Exterior

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 ￥18,334
￥66,779 total
includes taxes & fees
Jul 12 - Jul 13
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
Property grounds

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 ￥27,733
￥80,429 total
includes taxes & fees
Aug 8 - Aug 9
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

Sheraton Maui Resort & Spa

Sheraton Maui Resort & Spa

10/10 Excellent
"The property was beautiful and the staff were all so great. It is high season so the one issue I noticed is there is definitely not enough lounge chairs at the pool to accommodate all the people who are staying at the resort. All the hotels are like this actually. Resort should provide chairs to guests free of charge for the beach at the rate you are paying to stay there a night."
Lauren 2-night trip
Posted 2 hours ago
Sheraton Maui Resort & Spa

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?

Stunning Views & Tropical Tranquility 429 LS: Visitors like this Kaanapali Hillside vacation home rental. It is located on the beach and has a balcony, a garden, and a barbecue grill 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 vacation with amenities like a 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 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.