Explore Kaanapali Hillside, HI Vacation Rentals
Condo
10.0Exceptional
(177 Reviews)
1 Bedroom
1 Bath
2 Guests
938 ft²
Private Pool
Oceanfront
Hot Tub
Parking
US $621/Night
7 Nights - US $4,350
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
(22 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Hot Tub
- Parking
- Pool
US $575/Night
7 Nights - US $4,025
Condo
10.0Exceptional
(173 Reviews)
1 Bedroom
1 Bath
4 Guests
938 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $438/Night
7 Nights - US $3,066
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
(172 Reviews)
3 Bedrooms
3 Baths
8 Guests
2700 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $1,022/Night
7 Nights - US $7,156
Condo
10.0Exceptional
(160 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $400/Night
7 Nights - US $2,801
Condo
10.0Exceptional
(155 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $1,176/Night
7 Nights - US $8,229
Cottage
10.0Exceptional
(153 Reviews)
2 Bedrooms
2 Baths
4 Guests
1700 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $507/Night
7 Nights - US $3,551
Luxury Places to Stay in Kaanapali Hillside
Over 9527+ Luxury Places to Stay in or Near Kaanapali Hillside
Condo
10 Bedrooms
10 Baths
28 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
View
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Condo
9 Bedrooms
9 Baths
28 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
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Condo
8 Bedrooms
8 Baths
24 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
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Hotel
6 Baths
Breakfast- Pool
- Balcony/Terrace
Kitchen
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Condo
7 Bedrooms
7 Baths
22 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
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Hotel
2 Baths
- Breakfast
- Pool
- Balcony/Terrace
- Kitchen
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Condo
8 Bedrooms
8 Baths
24 Guests
4693 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
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Condo
8 Bedrooms
8 Baths
24 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
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Villa
10.0Exceptional
(5 Reviews)
9 Bedrooms
9 Baths
24 Guests
6141 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
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Top-Rated Vacation Rentals with a Pool in Kaanapali Hillside
Over 7222+ Top-Rated Vacation Rentals with a Pool in or Near Kaanapali Hillside
Condo
10.0Exceptional
(295 Reviews)
1 Bedroom
1 Bath
2 Guests
938 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $566/Night
7 Nights - US $3,964
Condo
10.0Exceptional
(235 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $1,815/Night
7 Nights - US $12,705
Condo
10.0Exceptional
(231 Reviews)
2 Bedrooms
2 Baths
6 Guests
1150 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $885/Night
7 Nights - US $6,195
Condo
10.0Exceptional
(226 Reviews)
1 Bedroom
1 Bath
4 Guests
600 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $737/Night
7 Nights - US $5,158
Condo
10.0Exceptional
(223 Reviews)
3 Bedrooms
3 Baths
10 Guests
1600 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $1,501/Night
7 Nights - US $10,508
Condo
10.0Exceptional
(219 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $149/Night
7 Nights - US $1,041
Condo
10.0Exceptional
(216 Reviews)
3 Bedrooms
3 Baths
8 Guests
1200 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $983/Night
7 Nights - US $6,879
Condo
10.0Exceptional
(213 Reviews)
1 Bedroom
1 Bath
4 Guests
820 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $993/Night
7 Nights - US $6,951
Condo
10.0Exceptional
(208 Reviews)
2 Bedrooms
2 Baths
6 Guests
1080 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $625/Night
7 Nights - US $4,377
Pet-Friendly Vacation Rentals in Kaanapali Hillside
Over 37+ Pet-Friendly Vacation Rentals in or Near Kaanapali Hillside
Condo
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $802/Night
7 Nights - US $5,612
Apartment
1 Bedroom
1 Bath
3 Guests
538.2 ft²
- Kitchen
Air Conditioner
Internet
Pet Friendly
US $5,572/Night
7 Nights - US $39,004
Condo
9.8Exceptional
(54 Reviews)
1 Bedroom
1 Bath
6 Guests
1001 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $624/Night
7 Nights - US $4,365
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
Apartment
9.6Exceptional
(82 Reviews)
1 Bedroom
1 Bath
4 Guests
507 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $299/Night
7 Nights - US $2,094
Condo
9.2Exceptional
(63 Reviews)
2 Bedrooms
1 Bath
3 Guests
432 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $439/Night
7 Nights - US $3,073
Condo
9.2Exceptional
(23 Reviews)
2 Bedrooms
1 Bath
6 Guests
676 ft²
- Parking
- Pool
- Kitchen
- Internet
US $210/Night
7 Nights - US $1,467
Condo
8.8Fabulous
(5 Reviews)
1 Bedroom
1 Bath
4 Guests
570 ft²
- Parking
- Kitchen
- Internet
- Pet Friendly
US $210/Night
7 Nights - US $1,467
House
5 Bedrooms
5 Baths
8 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $896/Night
7 Nights - US $6,272
Large Vacation Homes & Villas in Kaanapali Hillside
Over 1763+ Large Vacation Homes & Villas in or Near Kaanapali Hillside
House
10.0Exceptional
(66 Reviews)
6 Bedrooms
3 Baths
12 Guests
3500 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $1,846/Night
7 Nights - US $12,925
House
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
12 Guests
2551.05 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $2,518/Night
7 Nights - US $17,624
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
(45 Reviews)
3 Bedrooms
3 Baths
10 Guests
1940 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $3,121/Night
7 Nights - US $21,845
House
10.0Exceptional
(1 Review)
65 Bedrooms
104 Baths
295 Guests
1671.45 ft²
- Parking
- Internet
Child Friendly
Security/Safety
US $1,264/Night
7 Nights - US $8,845
Villa
9.8Exceptional
(61 Reviews)
2 Bedrooms
2 Baths
8 Guests
1200 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $1,048/Night
7 Nights - US $7,338
Villa
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
1345 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $1,557/Night
7 Nights - US $10,901
Condo
9.6Exceptional
(43 Reviews)
3 Bedrooms
3 Baths
10 Guests
2217 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $3,060/Night
7 Nights - US $21,418
Condo
8.8Fabulous
(43 Reviews)
3 Bedrooms
2 Baths
10 Guests
1110 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $578/Night
7 Nights - US $4,049
Wheelchair Accessible Vacation Homes in Kaanapali Hillside
Over 4596+ Wheelchair Accessible Vacation Homes in or Near Kaanapali Hillside
Condo
10.0Exceptional
(152 Reviews)
2 Bedrooms
1 Bath
5 Guests
851 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $373/Night
7 Nights - US $2,610
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
1463.89 ft²
- Hot Tub
- Pool
- View
- Child Friendly
US $365/Night
7 Nights - US $2,552
Apartment
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Parking
- Pool
- Ocean View
US $357/Night
7 Nights - US $2,499
Condo
10.0Exceptional
(150 Reviews)
2 Bedrooms
2 Baths
4 Guests
1150 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $760/Night
7 Nights - US $5,318
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
602.78 ft²
- Pool
- Balcony/Terrace
- View
- Child Friendly
US $424/Night
7 Nights - US $2,968
Condo
10.0Exceptional
(114 Reviews)
3 Bedrooms
3 Baths
9 Guests
2050 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $1,035/Night
7 Nights - US $7,247
Condo
10.0Exceptional
(96 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $930/Night
7 Nights - US $6,509
Condo
10.0Exceptional
(86 Reviews)
1 Bedroom
2 Baths
4 Guests
938 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $503/Night
7 Nights - US $3,518
Condo
10.0Exceptional
(77 Reviews)
1 Bedroom
2 Baths
4 Guests
1100 ft²
- Oceanfront
- Parking
- Pool
Spa
US $668/Night
7 Nights - US $4,676
Kaanapali Hillside Villas and Airbnb Homes Under $200
Over 150+ Kaanapali Hillside Villas and Airbnb Homes Under $200
Condo
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Parking
- Pool
- Ocean View
- View
US $199/Night
7 Nights - US $1,394
Hotel
8.8Fabulous
(11 Reviews)
4 Baths
1006.43 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $157/Night
7 Nights - US $1,099
Condo
9.4Exceptional
(8 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $106/Night
7 Nights - US $745
Condo
9.8Exceptional
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
452 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $176/Night
7 Nights - US $1,229
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
495.14 ft²
- Parking
- Pool
- Air Conditioner
- Internet
US $150/Night
7 Nights - US $1,050
Condo
9.2Exceptional
(7 Reviews)
1 Bedroom
1 Bath
2 Guests
452 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $183/Night
7 Nights - US $1,283
Condo
6.0Good
(1 Review)
1 Bedroom
1 Bath
6 Guests
800 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $190/Night
7 Nights - US $1,332
New
Condo
1 Bedroom
1 Bath
2 Guests
452 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $165/Night
7 Nights - US $1,156
New
Condo
1 Bedroom
1 Bath
2 Guests
452 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $156/Night
7 Nights - US $1,095
Instantly Bookable Vacation Homes in Kaanapali Hillside
Over 5699+ Instantly Bookable Vacation Homes in or Near Kaanapali Hillside
Condo
10.0Exceptional
(133 Reviews)
2 Bedrooms
2 Baths
8 Guests
2100 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $702/Night
7 Nights - US $4,914
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
(69 Reviews)
2 Bedrooms
1 Bath
6 Guests
915 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $602/Night
7 Nights - US $4,213
Condo
10.0Exceptional
(63 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $619/Night
7 Nights - US $4,334
Condo
9.8Exceptional
(214 Reviews)
1 Bedroom
1 Bath
4 Guests
509 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $379/Night
7 Nights - US $2,656
Condo
9.8Exceptional
(151 Reviews)
2 Bedrooms
2 Baths
6 Guests
900 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $393/Night
7 Nights - US $2,749
Condo
9.8Exceptional
(143 Reviews)
1 Bedroom
1 Bath
2 Guests
900 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $799/Night
7 Nights - US $5,592
Condo
9.8Exceptional
(135 Reviews)
2 Bedrooms
2 Baths
6 Guests
900 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $649/Night
7 Nights - US $4,545
Condo
9.8Exceptional
(114 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $458/Night
7 Nights - US $3,203
Book a Last Minute Place to Stay in Kaanapali Hillside
About Kaanapali Hillside Vacation Rentals
Explore more than 9536 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 853.86 ft². Prices average US $1,542 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 | 1507 |
| Vacation Homes | 590 |
| Villas | 449 |
| 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 9536 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!
- Maui Oceanfront Corner Condo - 270° Panoramic Views on Kaanapali Beach
- 5 Star Oceanview Studio-Honua Kai Resort Konea 437-Beach Access, Pools,
- 3BD Oceanfront Retreat w/Lanai, Floor-to-Ceiling Views & Modern Kitchen - Honua Kai 825
- The Best Ocean View Studio Condo at the Royal Kahana Oceanfront Resort. With AC.
- 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 🏝🏖
- Great Rates! Intimate Ocean/Beach Condo, Couple's Paradise!
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 9536 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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