9153+ Villas for Rent and Private Getaways in Kaanapali Hillside |
Explore Kaanapali Hillside Vacation Rentals
10.0
Exceptional
(165 Reviews)
938 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Private Pool
- Oceanfront
- Hot Tub
US $704/Night
For 7 Nights US $4,927
New
3003.13 ft²
12 Guests
3 Bedrooms
3 Bathrooms
House
- Private Beach
- Pool
- Ocean View
US $980/Night
For 7 Nights US $6,860
10.0
Exceptional
(11 Reviews)
1 Bedroom
1 Bathroom
Ocean View
Condo
- Hot Tub
- Spa
- Pool
US $575/Night
For 7 Nights US $4,025
10.0
Exceptional
(164 Reviews)
938 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $401/Night
For 7 Nights US $2,810
9.5
Exceptional
(192 Reviews)
258.33 ft²
2 Guests
1 Bedroom
1 Bathroom
Bed & Breakfast
- Hot Tub
- Pool
- Balcony/Terrace
US $129/Night
For 7 Nights US $903
10.0
Exceptional
(158 Reviews)
2700 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Condo
- Hot Tub
- Pool
- Ocean View
US $1,084/Night
For 7 Nights US $7,591
10.0
Exceptional
(155 Reviews)
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Hot Tub
- Pool
- Ocean View
US $415/Night
For 7 Nights US $2,908
10.0
Exceptional
(147 Reviews)
1150 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Private Pool
- Oceanfront
- Hot Tub
US $628/Night
For 7 Nights US $4,398
10.0
Exceptional
(146 Reviews)
1700 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Oceanfront
- Pool
- Ocean View
US $412/Night
For 7 Nights US $2,882
Luxury Places to Stay in Kaanapali Hillside
Over 9144+ Luxury Places to Stay in or Near Kaanapali Hillside
New
2 Bathrooms
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Breakfast
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New
6985.78 ft²
30 Guests
11 Bedrooms
11 Bathrooms
Free Cancellation
Apartment
- Oceanfront
- Spa
- Ocean View
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New
5048.27 ft²
22 Guests
8 Bedrooms
8 Bathrooms
Free Cancellation
Apartment
- Oceanfront
- Spa
- Ocean View
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New
30 Guests
11 Bedrooms
11 Bathrooms
Family Friendly
Condo
- Balcony/Terrace
- Kitchen
- Internet
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New
Honua Kai Hokulani | 4 Free Rental Cars | KBM Resorts | Ocean Front | 4 Units, 11 Bedrooms | ML-1123
6986 ft²
30 Guests
11 Bedrooms
11 Bathrooms
Family Friendly
Condo
- Balcony/Terrace
- Kitchen
- Internet
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New
6501.4 ft²
28 Guests
10 Bedrooms
10 Bathrooms
Ocean View
Apartment
- Oceanfront
- Spa
- Ocean View
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New
7136.47 ft²
30 Guests
11 Bedrooms
11 Bathrooms
Free Cancellation
Apartment
- Oceanfront
- Spa
- Ocean View
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New
26 Guests
9 Bedrooms
9 Bathrooms
Family Friendly
Condo
- Balcony/Terrace
- Kitchen
- Internet
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10.0
Exceptional
(20 Reviews)
26 Guests
11 Bedrooms
9 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
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Top-Rated Vacation Rentals with a Pool in Kaanapali Hillside
Over 7147+ Top-Rated Vacation Rentals with a Pool in or Near Kaanapali Hillside
10.0
Exceptional
(312 Reviews)
1240 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $796/Night
For 7 Nights US $5,574
10.0
Exceptional
(277 Reviews)
938 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $951/Night
For 7 Nights US $6,657
10.0
Exceptional
(253 Reviews)
901 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Private Pool
- Oceanfront
- Hot Tub
US $560/Night
For 7 Nights US $3,917
10.0
Exceptional
(248 Reviews)
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Condo
- Pool
- Ocean View
- Balcony/Terrace
US $465/Night
For 7 Nights US $3,254
10.0
Exceptional
(245 Reviews)
523 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Hot Tub
- Spa
- Pool
US $402/Night
For 7 Nights US $2,813
10.0
Exceptional
(243 Reviews)
600 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $495/Night
For 7 Nights US $3,467
10.0
Exceptional
(237 Reviews)
566 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
US $261/Night
For 7 Nights US $1,828
10.0
Exceptional
(234 Reviews)
1100 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Pool
- Ocean View
US $1,184/Night
For 7 Nights US $8,291
10.0
Exceptional
(234 Reviews)
1400 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Pool
- Ocean View
US $805/Night
For 7 Nights US $5,632
Pet-Friendly Vacation Rentals in Kaanapali Hillside
Over 27+ Pet-Friendly Vacation Rentals in or Near Kaanapali Hillside
10.0
Exceptional
(30 Reviews)
777 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
US $361/Night
For 7 Nights US $2,529
New
538.2 ft²
3 Guests
1 Bedroom
1 Bathroom
Apartment
- Breakfast
- Pet Friendly
- Air Conditioner
US $5,572/Night
For 7 Nights US $39,004
10.0
Exceptional
(11 Reviews)
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $533/Night
For 7 Nights US $3,729
9.0
Exceptional
(258 Reviews)
487.06 ft²
80 Guests
20 Bathrooms
Ocean View
Resort
- Oceanfront
- Hot Tub
- Spa
US $537/Night
For 7 Nights US $3,758
9.8
Exceptional
(52 Reviews)
1000 ft²
6 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $522/Night
For 7 Nights US $3,654
10.0
Exceptional
(1 Review)
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Spa
- Fireplace/Heating
US $949/Night
For 7 Nights US $6,643
New
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Spa
- Fireplace/Heating
US $1,271/Night
For 7 Nights US $8,897
New
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Spa
- Fireplace/Heating
US $972/Night
For 7 Nights US $6,804
New
480 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Hot Tub
- Spa
- Fireplace/Heating
US $525/Night
For 7 Nights US $3,672
Large Vacation Homes & Villas in Kaanapali Hillside
Over 1631+ Large Vacation Homes & Villas in or Near Kaanapali Hillside
10.0
Exceptional
(64 Reviews)
3500 ft²
12 Guests
6 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $2,206/Night
For 7 Nights US $15,441
10.0
Exceptional
(2 Reviews)
1060.24 ft²
42 Guests
13 Bedrooms
12 Bathrooms
Ocean View
Apartment
- Private Beach
- Oceanfront
- Hot Tub
US $495/Night
For 7 Nights US $3,468
9.8
Exceptional
(147 Reviews)
6500 ft²
16 Guests
6 Bedrooms
7 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $2,495/Night
For 7 Nights US $17,468
10.0
Exceptional
(41 Reviews)
1940 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Balcony/Terrace
- Kitchen
- Parking
US $2,807/Night
For 7 Nights US $19,652
10.0
Exceptional
(1 Review)
2855.13 ft²
40 Guests
4 Bedrooms
15 Bathrooms
Apartment
- Private Pool
- Oceanfront
- Hot Tub
US $3,885/Night
For 7 Nights US $27,195
9.8
Exceptional
(59 Reviews)
1200 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Hot Tub
- Spa
- Pool
US $1,420/Night
For 7 Nights US $9,937
10.0
Exceptional
(11 Reviews)
1345 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Hot Tub
- Spa
- Fireplace/Heating
US $1,454/Night
For 7 Nights US $10,180
9.6
Exceptional
(42 Reviews)
2217 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Balcony/Terrace
- Kitchen
- Parking
US $3,455/Night
For 7 Nights US $24,182
9.2
Exceptional
(7 Reviews)
1700 ft²
12 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Hot Tub
- Pool
- Ocean View
US $2,385/Night
For 7 Nights US $16,693
Wheelchair Accessible Vacation Homes in Kaanapali Hillside
Over 3908+ Wheelchair Accessible Vacation Homes in or Near Kaanapali Hillside
10.0
Exceptional
(143 Reviews)
851 ft²
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $406/Night
For 7 Nights US $2,844
8.8
Fabulous
(11 Reviews)
1006.43 ft²
4 Bathrooms
Hotel
- Oceanfront
- Pool
- Ocean View
US $157/Night
For 7 Nights US $1,099
10.0
Exceptional
(4 Reviews)
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
US $357/Night
For 7 Nights US $2,499
10.0
Exceptional
(142 Reviews)
1100 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Pool
- Ocean View
US $1,176/Night
For 7 Nights US $8,229
New
10.01 ft²
8 Guests
3 Bedrooms
3 Bathrooms
House
- Pool
- Ocean View
- View
US $2,784/Night
For 7 Nights US $19,488
10.0
Exceptional
(112 Reviews)
2050 ft²
9 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Condo
- Hot Tub
- Pool
- Ocean View
US $1,400/Night
For 7 Nights US $9,801
10.0
Exceptional
(94 Reviews)
1400 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Private Pool
- Hot Tub
- Pool
US $733/Night
For 7 Nights US $5,134
10.0
Exceptional
(85 Reviews)
938 ft²
4 Guests
1 Bedroom
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $527/Night
For 7 Nights US $3,690
10.0
Exceptional
(75 Reviews)
1100 ft²
4 Guests
1 Bedroom
2 Bathrooms
Ocean View
Condo
- Spa
- Pool
- Ocean View
US $630/Night
For 7 Nights US $4,410
Kaanapali Hillside Villas and Airbnb Homes Under $200
Over 167+ Kaanapali Hillside Villas and Airbnb Homes Under $200
9.4
Exceptional
(212 Reviews)
506 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Private Pool
- Hot Tub
- Pool
US $139/Night
For 7 Nights US $972
10.0
Exceptional
(3 Reviews)
764.24 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- View
- Breakfast
- Parking
US $147/Night
For 7 Nights US $1,029
9.4
Exceptional
(8 Reviews)
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $106/Night
For 7 Nights US $745
9.4
Exceptional
(23 Reviews)
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
US $199/Night
For 7 Nights US $1,390
10.0
Exceptional
(1 Review)
10.76 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Pool
- Parking
- Internet
US $193/Night
For 7 Nights US $1,351
9.2
Exceptional
(50 Reviews)
560 ft²
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Ocean View
- Balcony/Terrace
US $195/Night
For 7 Nights US $1,366
9.0
Exceptional
(26 Reviews)
550 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Pool
- Balcony/Terrace
- Kitchen
US $186/Night
For 7 Nights US $1,305
8.0
Excellent
(8 Reviews)
631 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
US $195/Night
For 7 Nights US $1,368
7.4
Very Good
(3 Reviews)
676 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
US $197/Night
For 7 Nights US $1,377
Instantly Bookable Vacation Homes in Kaanapali Hillside
Over 5458+ Instantly Bookable Vacation Homes in or Near Kaanapali Hillside
10.0
Exceptional
(128 Reviews)
2100 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $710/Night
For 7 Nights US $4,967
10.0
Exceptional
(1 Review)
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Pool
- Balcony/Terrace
US $542/Night
For 7 Nights US $3,792
10.0
Exceptional
(67 Reviews)
915 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $640/Night
For 7 Nights US $4,481
10.0
Exceptional
(61 Reviews)
600 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Pool
- Balcony/Terrace
US $362/Night
For 7 Nights US $2,532
9.8
Exceptional
(205 Reviews)
509 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
US $271/Night
For 7 Nights US $1,895
9.8
Exceptional
(143 Reviews)
900 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $630/Night
For 7 Nights US $4,413
9.8
Exceptional
(135 Reviews)
900 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $750/Night
For 7 Nights US $5,249
9.8
Exceptional
(129 Reviews)
900 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $561/Night
For 7 Nights US $3,929
9.8
Exceptional
(111 Reviews)
700 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $907/Night
For 7 Nights US $6,347
Book a Last Minute Place to Stay in Kaanapali Hillside
About Kaanapali Hillside Vacation Rentals
Explore more than 9153 vacation rentals available in Kaanapali Hillside. These accommodations, including vacation homes and HawaiiVillas properties, boast excellent amenities and exceptional value, blending comfort and luxury. Enjoy spaciousness and convenience at a HawaiiVillas property in Kaanapali Hillside.
Looking for last-minute deals or the best available offers on cottages, condos, private villas, and large vacation homes? With HawaiiVillas in Kaanapali Hillside, you can effortlessly compare various options with a simple click. Whether you seek properties with swimming pools, hot tubs, pet-friendly policies, or expansive master suites with large screen TVs, you'll find vacation rentals by owner (RBOs) and other popular Airbnb-style accommodations near Kaanapali Hillside. The average room size in accommodations near Kaanapali Hillside is 852.51 ft². Prices average US $1,367 per night.
HawaiiVillas streamlines and secures your search for vacation rentals in Kaanapali Hillside, often offering savings of 30-40% compared to hotel prices. Start your search today and book with confidence.
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Top Rental Accommodation Types in Kaanapali Hillside
| Type | Count |
|---|---|
| Holiday Apartments | 1398 |
| Vacation Homes | 553 |
| Villas | 434 |
| Cottages | 20 |
Use these Quick Filters to Find a Vacation Rental in Kaanapali Hillside
★ Pro Tip: HawaiiVillas simplifies comparison of top listings across various online vacation rental platforms like Booking.com and others. Use the Advanced Filter feature to switch effortlessly between HawaiiVillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, property types, cancellation policies, prices, and more. These tools streamline the search for your ideal accommodation for your next vacation in Kaanapali Hillside.
Weather in Kaanapali Hillside, HI
View the weather forecast for Kaanapali Hillside before booking your Kaanapali Hillside Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Kaanapali Hillside, HI
HawaiiVillas offers a wide selection of top attractions nearby Kaanapali Hillside . Research things to do on your vacation before you visit Kaanapali Hillside.
Frequently Asked Questions About Kaanapali Hillside?
What are the top vacation rentals in Kaanapali Hillside?
Currently, HawaiiVillas lists over 9153 properties in the Kaanapali Hillside area for 2026, with more being added continuously. By consolidating listings from various websites, HawaiiVillas provides a wide selection of top properties in Kaanapali Hillside.
- HOKULANI 436-CORNER UNIT 2BD/2BA w/OCEAN & MOUNTAIN VIEWS,505SQFT LANAI BALCONY
- Luxury OCEAN FRONT Truly 5 Star with A/C, 20' From The Water At Pikake. No fees
- Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014
- SLEEP NUMBER BED! #759 1bdrm-A Guest Favorite-Ocean/Beach View w/XBOX & ROKU!
- nRead Our Reviews and See Why Our Guests Love to Stay with Us.
- The Whaler! ~Beautifully remodeled ground floor courtyard studio~
- Luxury Studio-Ocean View-Honua Kai Resort Konea215- Pools,Beach Access,5 star
- Views! Views!
- Maui Resort Rentals: Hokulani 605 – Premier 6th-Floor Oceanview Penthouse | Closest 2BR Column to the Ocean!
- MAHANA ON THE BEACH-PREMIUM 11th FL CORNER 270 DEG OCEANFRONT VIEWS 2BR/2BA
How many vacation rentals have private pools in Kaanapali Hillside?
Discover 305 vacation rentals featuring private pools near Kaanapali Hillside. Highly-rated HawaiiVillas properties with swimming pool access include:
- Stunning views over the Pacific Ocean
- KBM Resorts FREE CAR Kaanapali Royal 2-Bedroom Condo an Island Inspired Gem KRO-G201
- Vast Ocean View & 15% OFF!!
- The Best Ocean View Studio Condo at the Royal Kahana Oceanfront Resort
Which vacation homes in Kaanapali Hillside are best for families?
If you're searching for a family-friendly vacation residence in Kaanapali Hillside, explore one of these highly-rated properties, all praised for their excellent reviews among families or groups visiting Kaanapali Hillside:
How many Hawaii.Villas vacation rentals are available in Kaanapali Hillside?
At present, HawaiiVillas showcases more than 9153 properties available in the Kaanapali Hillside area for 2026, with new listings added regularly. By aggregating listings from multiple sources, HawaiiVillas offers a diverse range of premier properties in Kaanapali Hillside.
People Also Ask
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