
Kaanapali Hillside Vacation Rentals
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Our top choices for Kaanapali Hillside vacation rentals

1. Aston Maui Kaanapali Villas
Aston Maui Kaanapali Villas
2. Aston Kaanapali Shores
Aston Kaanapali Shores
3. The Whaler Resort Kaanapali Beach
The Whaler Resort Kaanapali Beach
4. Napili Village Hotel
Napili Village Hotel
5. OUTRIGGER Honua Kai Resort & Spa
OUTRIGGER Honua Kai Resort & Spa
6. The Westin Ka'anapali Ocean Resort Villas
The Westin Ka'anapali Ocean Resort Villas
7. Napili Shores Maui by OUTRIGGER
Napili Shores Maui by OUTRIGGER
8. Marriott's Maui Ocean Club - Lahaina & Napili Towers
Marriott's Maui Ocean Club - Lahaina & Napili Towers
9. The Whaler 518 – Remodeled Ocean View Studio on Kāʻanapali Beach
The Whaler 518 – Remodeled Ocean View Studio on Kāʻanapali Beach
10. Kuleana Club - 316
Kuleana Club - 316
11. Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC
Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC
12. Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!
Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!
13. Beautiful Oceanfront Condo at Pikake 20 Feet From the Water A/C Amazing Views
Beautiful Oceanfront Condo at Pikake 20 Feet From the Water A/C Amazing Views
14. Summertime Special Prices!! Book Now!
Summertime Special Prices!! Book Now!
15. Napili Sunset on the Beach
Napili Sunset on the Beach
16. The Westin Nanea Ocean Villas, Ka'anapali
The Westin Nanea Ocean Villas, Ka'anapali
17. Direct Ocean Front~Kaanapali Beach~West Maui Paradise Welcomes You!
Direct Ocean Front~Kaanapali Beach~West Maui Paradise Welcomes You!
18. Spacious Studio Close to Ocean Heated Pool - Kaleialoha 402
Spacious Studio Close to Ocean Heated Pool - Kaleialoha 402
19. Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742
Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742
20. Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!
Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!Find vacation rentals that suit your style
Top Kaanapali Hillside Hotel Reviews

Maui Seaside Hotel
Find out more about Kaanapali Hillside
You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Kaanapali Hillside. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.




































































