Holiday Rentals in Kaanapali Hillside

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Holiday Rentals in Kaanapali Hillside

Charming Direct Oceanfront North Shore Beach House

9.0 out of 10, Wonderful, (32)
The price is €695
includes taxes & fees
28 Jul - 29 Jul
Charming Direct Oceanfront North Shore Beach House

Beautiful 3-bedroom townhome in Kihei

9.0 out of 10, Wonderful, (2)
"This stay was very nice, me and my friends enjoyed the things provided in the house specially the snorkeling equipment. Would highly recommend for any family or friends traveling to Maui. This home was convenient for any beaches, shops, or any outdoor activity."
The price is €400
includes taxes & fees
2 Aug - 3 Aug
Beautiful 3-bedroom townhome in Kihei

Maaleaa Surf C5 Oceanfront townhouse on miles of Sandy Beach

10.0 out of 10, Exceptional, (6)
"Clean, cozy and nicely designed. This condo has an amazing view and access to the beach and pool. Kitchen is well equipped, even has a milk warmer/frother which I appreciate so much as a lover of lattes. We'll happily stay here again on our next trip to Maui. "
The price is €611
includes taxes & fees
8 Jul - 9 Jul
Maaleaa Surf C5 Oceanfront townhouse on miles of Sandy Beach

Sugar Beach 417 Direct Row Beach Views in Beautifully Upgraded Ocean front Condo Home

The price is €501
includes taxes & fees
13 Jul - 14 Jul
Sugar Beach 417 Direct Row Beach Views in Beautifully Upgraded Ocean front Condo Home

Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub

10.0 out of 10, Exceptional, (1)
"Place was great and would definitely stay again! There was a nice yard and a closet full of beach gear, chairs and coolers we made use of. Only thing that would have been better was if the hot tub was not on a timer that shuts off later at night. Great spot!!"
The price is €1,593
includes taxes & fees
15 Jul - 16 Jul
Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub

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

9.8 out of 10, Exceptional, (109)
"Quiet neighborhood setting. Nice backyard for relaxing. Well equipped with beach accessories including snorkel gear. Large whirlpool tub and comfortable bed. Be prepared for carrying luggage to second floor."
The price is €559
includes taxes & fees
27 Jul - 28 Jul
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

9.6 out of 10, Exceptional, (106)
"Nice property with plenty of space, great location on the island, super communicative and polite host, and such a great backyard/outdoor area. Would highly recommend!"
The price is €1,137
includes taxes & fees
15 Jul - 16 Jul
Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

Menehune Shores 121: 2 BR, 2 BA Condominium in Kihei, Sleeps 4

10.0 out of 10, Exceptional, (186)
"We all loved it!"
The price is €614
includes taxes & fees
19 Jul - 20 Jul
Menehune Shores 121: 2 BR, 2 BA Condominium in Kihei, Sleeps 4

Oceanfront Paradise in North Kihei

The price is €498
includes taxes & fees
25 Jul - 26 Jul
Oceanfront Paradise in North Kihei

NB 210 Direct Ocean Views from this Napili Bay Studio Steps from the Sand Ocean

The price is €623
includes taxes & fees
3 Aug - 4 Aug
NB 210 Direct Ocean Views from this Napili Bay Studio Steps from the Sand Ocean

RK 616 Bright Blue Ocean Views and Sunsets from this Studio Condo in the heart of West Maui!

The price is €544
includes taxes & fees
3 Aug - 4 Aug
RK 616 Bright Blue Ocean Views and Sunsets from this Studio Condo in the heart of West Maui!

Oceanfront getaway with a furnished patio, views, pool, & high-speed WiFi

9.6 out of 10, Exceptional, (9)
"We greatly enjoyed our stay in this unit and on this property. The unit was exceptionally clean, well-maintained, and the kitchen was exceptional. The beds gave you the option of either a soft surface or a firm mattress. Excellent view from the lanai. And the snorkeling in Honokeana Bay was exceptional! Sea turtles galore! Will be back next year!"
The price is €442
includes taxes & fees
15 Jul - 16 Jul
Oceanfront getaway with a furnished patio, views, pool, & high-speed WiFi

KS 826 Enjoy Ocean and Neighbor Island Views from this 1BD Kaanapali Shores Condo

The price is €609
includes taxes & fees
3 Aug - 4 Aug
KS 826 Enjoy Ocean and Neighbor Island Views from this 1BD Kaanapali Shores Condo

KS 529 Oceanview 2BD Condo at Kaanapali Shores Steps to the Pools and Hot Tub!

The price is €757
includes taxes & fees
5 Aug - 6 Aug
KS 529 Oceanview 2BD Condo at Kaanapali Shores Steps to the Pools and Hot Tub!

KPL 34 North Kaanapali Hillside 2BD Condo with Ocean Views and Sunsets

The price is €703
includes taxes & fees
5 Aug - 6 Aug
KPL 34 North Kaanapali Hillside 2BD Condo with Ocean Views and Sunsets

Oceanfront - 2 Bedroom - Westin Kaanapali Ocean Resort Villas - Full Resort Access

9.6 out of 10, Exceptional, (23)
"This resort is highly recommended, perfect location, perfect facilities for family with small kids and grandparents."
The price is €6,540
includes taxes & fees
27 Jul - 28 Jul
Oceanfront - 2 Bedroom - Westin Kaanapali Ocean Resort Villas - Full Resort Access

Maui Ka’anapali Villas #C261: Studio garden view condo at Beach Front Resort on

The price is €422
includes taxes & fees
16 Jul - 17 Jul
Maui Ka’anapali Villas #C261: Studio garden view condo at Beach Front Resort on

Maui Ka’anapali Villas #137: Studio garden view condo at Beach Front Resort on N

The price is €414
includes taxes & fees
12 Jul - 13 Jul
Maui Ka’anapali Villas #137: Studio garden view condo at Beach Front Resort on N

Aston Maui Kaanapali Villas #260 - 2 Sleeping Areas, 2 Bathrooms, 4 Guests

The price is €513
includes taxes & fees
17 Jul - 18 Jul
Aston Maui Kaanapali Villas #260 - 2 Sleeping Areas, 2 Bathrooms, 4 Guests
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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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?

#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool: This holiday home rental outside of Kaanapali Hillside is located on the beach, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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 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.