Explore Kaanapali Hillside Vacation Rentals
Condo
10.0Exceptional
(170 Reviews)
1 Bedroom
1 Bath
2 Guests
938 ft²
Private Pool
Oceanfront
Hot Tub
Parking
US $611/Night
7 Nights - US $4,278
House
- Lahaina
- ·
- Historic Lahaina Front Street
- 1.10 mi to center
3 Bedrooms
3 Baths
12 Guests
3003.13 ft²
Private Beach- Parking
Pool
Ocean View
US $980/Night
7 Nights - US $6,860
Condo
10.0Exceptional
(17 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Parking
- Pool
Spa
US $575/Night
7 Nights - US $4,025
Condo
10.0Exceptional
(168 Reviews)
1 Bedroom
1 Bath
4 Guests
938 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $456/Night
7 Nights - US $3,189
Bed & Breakfast
- Lahaina
- ·
- Historic Lahaina Front Street
- 1.48 mi to center
9.5Exceptional
(192 Reviews)
1 Bedroom
1 Bath
2 Guests
258.33 ft²
- Hot Tub
- Parking
- Pool
Balcony/Terrace
US $129/Night
7 Nights - US $903
Condo
10.0Exceptional
(165 Reviews)
3 Bedrooms
3 Baths
8 Guests
2700 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $1,190/Night
7 Nights - US $8,331
Condo
10.0Exceptional
(157 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $488/Night
7 Nights - US $3,419
Cottage
10.0Exceptional
(151 Reviews)
2 Bedrooms
2 Baths
4 Guests
1700 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $462/Night
7 Nights - US $3,233
Condo
10.0Exceptional
(150 Reviews)
2 Bedrooms
2 Baths
4 Guests
1150 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $754/Night
7 Nights - US $5,275
Luxury Places to Stay in Kaanapali Hillside
Over 9160+ Luxury Places to Stay in or Near Kaanapali Hillside
Condo
11 Bedrooms
11 Baths
28 Guests
- Balcony/Terrace
Kitchen
Internet
Child Friendly
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Condo
9 Bedrooms
9 Baths
28 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
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Condo
8 Bedrooms
8 Baths
22 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
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Condo
7 Bedrooms
7 Baths
22 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
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Condo
7 Bedrooms
7 Baths
22 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
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Condo
7 Bedrooms
7 Baths
22 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
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Hotel
2 Baths
Breakfast- Pool
- Balcony/Terrace
- Kitchen
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Condo
9 Bedrooms
9 Baths
26 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
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Hotel
1 Bath
- Breakfast
- Pool
- Balcony/Terrace
- Kitchen
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Top-Rated Vacation Rentals with a Pool in Kaanapali Hillside
Over 7041+ Top-Rated Vacation Rentals with a Pool in or Near Kaanapali Hillside
Condo
10.0Exceptional
(286 Reviews)
1 Bedroom
1 Bath
2 Guests
938 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $866/Night
7 Nights - US $6,059
Condo
10.0Exceptional
(234 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $1,382/Night
7 Nights - US $9,677
Condo
10.0Exceptional
(222 Reviews)
3 Bedrooms
3 Baths
10 Guests
1600 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $1,343/Night
7 Nights - US $9,401
Condo
10.0Exceptional
(221 Reviews)
1 Bedroom
1 Bath
4 Guests
600 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $526/Night
7 Nights - US $3,685
Condo
10.0Exceptional
(215 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $233/Night
7 Nights - US $1,634
Condo
10.0Exceptional
(211 Reviews)
3 Bedrooms
3 Baths
8 Guests
1200 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $946/Night
7 Nights - US $6,624
Condo
10.0Exceptional
(205 Reviews)
1 Bedroom
1 Bath
4 Guests
820 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $956/Night
7 Nights - US $6,694
Condo
10.0Exceptional
(204 Reviews)
2 Bedrooms
2 Baths
6 Guests
1080 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $629/Night
7 Nights - US $4,400
Apartment
10.0Exceptional
(201 Reviews)
1 Bedroom
1 Bath
4 Guests
585 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $595/Night
7 Nights - US $4,168
Pet-Friendly Vacation Rentals in Kaanapali Hillside
Over 27+ Pet-Friendly Vacation Rentals in or Near Kaanapali Hillside
Condo
10.0Exceptional
(32 Reviews)
1 Bedroom
1 Bath
4 Guests
777 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $318/Night
7 Nights - US $2,226
Apartment
1 Bedroom
1 Bath
3 Guests
538.2 ft²
- Breakfast
Air Conditioner- Internet
Pet Friendly
US $5,572/Night
7 Nights - US $39,004
Condo
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $632/Night
7 Nights - US $4,422
Apartment
9.0Exceptional
(1 Review)
1 Bedroom
2 Baths
4 Guests
904.17 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $519/Night
7 Nights - US $3,633
Condo
9.8Exceptional
(54 Reviews)
1 Bedroom
1 Bath
6 Guests
1000 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $645/Night
7 Nights - US $4,514
Villa
1 Bedroom
2 Baths
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $601/Night
7 Nights - US $4,209
House
5 Bedrooms
5 Baths
8 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $867/Night
7 Nights - US $6,071
Condo
- Lahaina
- ·
- Historic Lahaina Front Street
- 0.58 mi to center
3 Bedrooms
2 Baths
6 Guests
1375 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $435/Night
7 Nights - US $3,045
Villa
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Ocean View
View- Pet Friendly
- Child Friendly
US $909/Night
7 Nights - US $6,365
Large Vacation Homes & Villas in Kaanapali Hillside
Over 1723+ Large Vacation Homes & Villas in or Near Kaanapali Hillside
House
10.0Exceptional
(66 Reviews)
6 Bedrooms
3 Baths
12 Guests
3500 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,944/Night
7 Nights - US $13,607
Apartment
10.0Exceptional
(2 Reviews)
12 Bedrooms
11 Baths
38 Guests
1048.01 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Breakfast
US $475/Night
7 Nights - US $3,326
House
9.8Exceptional
(147 Reviews)
6 Bedrooms
7 Baths
16 Guests
6500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $2,495/Night
7 Nights - US $17,468
Condo
10.0Exceptional
(44 Reviews)
3 Bedrooms
3 Baths
10 Guests
1940 ft²
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
US $1,817/Night
7 Nights - US $12,720
House
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
12 Guests
2551.05 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $3,210/Night
7 Nights - US $22,470
Villa
9.6Exceptional
(60 Reviews)
2 Bedrooms
2 Baths
8 Guests
1200 ft²
- Hot Tub
- Parking
- Pool
- Spa
US $1,837/Night
7 Nights - US $12,859
Villa
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
1345 ft²
- Hot Tub
- Parking
- Pool
- Spa
US $1,589/Night
7 Nights - US $11,124
Condo
9.6Exceptional
(42 Reviews)
3 Bedrooms
3 Baths
10 Guests
2217 ft²
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
US $2,142/Night
7 Nights - US $14,991
Villa
9.2Exceptional
(7 Reviews)
3 Bedrooms
3 Baths
12 Guests
1700 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $3,403/Night
7 Nights - US $23,822
Wheelchair Accessible Vacation Homes in Kaanapali Hillside
Over 4314+ Wheelchair Accessible Vacation Homes in or Near Kaanapali Hillside
Condo
10.0Exceptional
(148 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $1,173/Night
7 Nights - US $8,214
Hotel
8.8Fabulous
(11 Reviews)
4 Baths
1006.43 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $157/Night
7 Nights - US $1,099
Apartment
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $357/Night
7 Nights - US $2,499
Condo
10.0Exceptional
(146 Reviews)
2 Bedrooms
1 Bath
5 Guests
851 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $505/Night
7 Nights - US $3,534
House
3 Bedrooms
3 Baths
8 Guests
10.01 ft²
- Parking
- Pool
- Ocean View
- View
US $2,784/Night
7 Nights - US $19,488
Condo
10.0Exceptional
(112 Reviews)
3 Bedrooms
3 Baths
9 Guests
2050 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $1,212/Night
7 Nights - US $8,485
Condo
10.0Exceptional
(96 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $824/Night
7 Nights - US $5,769
Condo
10.0Exceptional
(94 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $1,190/Night
7 Nights - US $8,332
Condo
10.0Exceptional
(86 Reviews)
1 Bedroom
2 Baths
4 Guests
938 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $483/Night
7 Nights - US $3,384
Kaanapali Hillside Villas and Airbnb Homes Under $200
Over 153+ Kaanapali Hillside Villas and Airbnb Homes Under $200
Condo
9.6Exceptional
(69 Reviews)
1 Bedroom
1 Bath
4 Guests
555 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $197/Night
7 Nights - US $1,377
House
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
10.76 ft²
- Parking
- Pool
- Internet
- Child Friendly
US $193/Night
7 Nights - US $1,351
Condo
9.4Exceptional
(8 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $106/Night
7 Nights - US $745
Condo
9.2Exceptional
(51 Reviews)
1 Bedroom
1 Bath
3 Guests
560 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $187/Night
7 Nights - US $1,309
Apartment
9.5Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Pool
- View
- Internet
US $196/Night
7 Nights - US $1,372
Apartment
1 Bedroom
1 Bath
4 Guests
480 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $189/Night
7 Nights - US $1,326
Condo
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $173/Night
7 Nights - US $1,211
Condo
1 Bedroom
1 Bath
3 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
US $97/Night
7 Nights - US $678
New
Apartment
1 Bedroom
1 Bath
2 Guests
267 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $190/Night
7 Nights - US $1,327
Instantly Bookable Vacation Homes in Kaanapali Hillside
Over 5445+ Instantly Bookable Vacation Homes in or Near Kaanapali Hillside
Condo
10.0Exceptional
(132 Reviews)
2 Bedrooms
2 Baths
8 Guests
2100 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $815/Night
7 Nights - US $5,703
Condo
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $542/Night
7 Nights - US $3,792
Condo
10.0Exceptional
(76 Reviews)
1 Bedroom
2 Baths
4 Guests
1100 ft²
- Parking
- Pool
- Spa
- Ocean View
US $738/Night
7 Nights - US $5,166
Condo
10.0Exceptional
(68 Reviews)
2 Bedrooms
1 Bath
6 Guests
915 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $644/Night
7 Nights - US $4,509
Condo
10.0Exceptional
(62 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $595/Night
7 Nights - US $4,162
Condo
9.8Exceptional
(210 Reviews)
1 Bedroom
1 Bath
4 Guests
509 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $270/Night
7 Nights - US $1,888
New
Condo
9.8Exceptional
(148 Reviews)
2 Bedrooms
2 Baths
6 Guests
900 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $458/Night
7 Nights - US $3,208
Condo
9.8Exceptional
(139 Reviews)
1 Bedroom
1 Bath
2 Guests
900 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $651/Night
7 Nights - US $4,554
Condo
9.8Exceptional
(131 Reviews)
2 Bedrooms
2 Baths
6 Guests
900 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $685/Night
7 Nights - US $4,797
Book a Last Minute Place to Stay in Kaanapali Hillside
About Kaanapali Hillside Vacation Rentals
Explore more than 9169 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 856.07 ft². Prices average US $1,408 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 | 1457 |
| Vacation Homes | 609 |
| Villas | 440 |
| Cottages | 19 |
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 9169 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.
- Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014
- Maui Resort Rentals: Hokulani 605 – Premier 6th-Floor Oceanview Penthouse | Closest 2BR Column to the Ocean!
- 3BD Oceanfront Retreat w/Lanai, Floor-to-Ceiling Views & Modern Kitchen - Honua Kai 825
- 5 Star Oceanview Studio-Honua Kai Resort Konea 437-Beach Access, Pools,
- The Best Ocean View Studio Condo at the Royal Kahana Oceanfront Resort. With A/C
- Beautifully Updated Penthouse Condo with Direct Ocean Views
- Oceanfront Mahana Condo 1BR/1BA Sweeping Views Ac, Pool
- 🏖Gorgeous 2BD/2BA LUXURY CONDO, OVER 200 5 STAR REVIEWS, Updated 🏝🏖
- The Whaler 814, Black Rock, All 5 Stars. Ocean and Beachfront Views
- Maui Kai 306 Oceanfront Condo, Fantastic Ocean Views
How many vacation rentals have private pools in Kaanapali Hillside?
Discover 270 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 Plantation Villa 3-Bedroom Condo with Short Walk to Beach Includes Beach Gear KPL-28
- Ocean View Suite at Royal Kahana
- 4BR Oceanview Estate | Infinity Pool + Pickleball Ct.
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 9169 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.
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