Masters at Kaanapali Hillside
50 Puu Anoano St, Lahaina, HI 96761
Masters at Kaanapali Hillside sits above the resort on close to 38 acres of landscaped grounds, built in 1991 around the top of the Royal Kaanapali Golf Course with sweeping ocean and mountain views. With 200 homes spread across 36 low-rise buildings, it was deliberately designed for low density, less than one building per acre, and layouts range from one-bedroom units to spacious three-bedroom homes.
Unlike many of the resort's beachfront towers, Masters is zoned residential and does not permit short-term vacation rental, which keeps it a quieter, more settled community than much of Kaanapali. Long-term rentals are still a normal part of the mix here, since the restriction is on short-term stays specifically. For buyers who want Kaanapali's views and golf-course setting without the turnover of a rental-heavy building, it is worth a look.
The short version
- ✦Hillside community above the Royal Kaanapali Golf Course, built in 1991
- ✦200 homes across 36 low-rise buildings on close to 38 acres
- ✦Deliberately low-density: less than one building per acre
- ✦Zoned residential, no short-term vacation rental permitted
- ✦2 pools, 2 hot tub spas, and 4 tennis/sport courts on site
By the numbers
- Year built
- 1991
- Total units
- 200
- Buildings
- 36 (2-story)
- Acreage
- 38 acres
- Floor plans
- 1 BR, 2 BR, 3 BR
- Unit size
- 901 to 2,156 sq ft
- Pets
- Pet-friendly
Short-term rental status
Masters at Kaanapali Hillside is zoned residential rather than apartment or hotel, and it does not appear on Maui County's currently published short-term occupancy lists. Short-term vacation rental is reported as not permitted here, which is consistent with its reputation as one of Kaanapali's quieter, low-density communities. Long-term rentals remain a normal part of the mix, since the restriction is on short-term stays specifically. Confirm current house rules with Diane if rental flexibility matters to your purchase.
Rules are actively changing as of 2026. Contact Diane for the current status of a specific unit.
On the grounds
Layouts
One bedroom
1 bd · 1 ba · 901 sq ft
One bedroom, larger
1 bd · 1.5 ba · 1,087 sq ft
Two bedroom
2 bd · 2 ba · 1,269 sq ft
Two bedroom, larger
2 bd · 2 ba · 1,728 sq ft
Two bedroom, 2.5 bath
2 bd · 2.5 ba · 1,917 sq ft
Two bedroom, largest
2 bd · 3 ba · 2,156 sq ft
Questions buyers ask
Where is Masters at Kaanapali Hillside located?
It sits at 50 Puu Anoano Street, on the hillside above the Royal Kaanapali Golf Course.
How big is Masters at Kaanapali Hillside?
Built in 1991, it holds 200 homes across 36 low-rise buildings on close to 38 acres, with one to three-bedroom layouts.
Can you short-term rent a condo at Masters at Kaanapali Hillside?
No. It is zoned residential and short-term vacation rental is not permitted, which sets it apart from many of Kaanapali's beachfront rental buildings. Long-term rentals are still possible, since the restriction is on short-term stays specifically.
Current listings at Masters at Kaanapali Hillside
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