Wailea Fairway Villas
3950 Kalai Waa St, Wailea, HI 96753
Wailea Fairway Villas is a quiet, golf-course community built in 1998: one hundred eighteen homes fill twenty-four two-story buildings on over 12 acres, with a mostly two-bedroom mix and a few larger three-bedroom units, plus a pool, hot tub, and exercise room tucked into the greenery along the fairways.
It is also one of a small handful of complexes in Wailea that does not permit short-term vacation rental at all. With 75% owner-occupancy, that keeps it feeling like a residential community rather than a rental play, similar in character to Wailea Town Center and Wailea Palms, though long-term tenants are still part of the normal mix here. For buyers who specifically want to avoid a rotating cast of vacation guests, that is a real point in its favor.
The short version
- ✦Vacation rental not permitted, a residential community
- ✦118 homes in 24 two-story buildings on over 12 acres
- ✦75% owner-occupied
- ✦Mostly 2-bedroom units with a smaller share of larger 3-bedrooms
- ✦Built in 1998 along the golf course
By the numbers
- Year built
- 1998
- Total units
- 118
- Buildings
- 24 (2-story)
- Acreage
- 12.374 acres
- Floor plans
- 2 BR, 3 BR
- Unit size
- 949 to 1,659 sq ft
- Owner-occupied
- 75%
- Pets
- Pet-friendly (confirm current house rules)
Short-term rental status
Available records show vacation rental is not permitted at Wailea Fairway Villas, and the complex does not appear on either of Maui County's officially published short-term rental lists, consistent with a primarily residential community. With 75% owner-occupancy, that lines up with what you would expect day to day. If a quiet, non-transient building matters to you, this is worth a look, though confirm current rules with Diane.
Rules are actively changing as of 2026. Contact Diane for the current status of a specific unit.
On the grounds
Layouts
Two bedroom
2 bd · 2 ba · 949 sq ft
Three bedroom
3 bd · 3 ba · 1,568 sq ft
Where it sits
Wailea Fairway Villas is highlighted below among its Wailea & Makena neighbors, with a small inset showing where Wailea & Makena sits on Maui overall.
Illustrative map, based on real Maui coastline data.
Questions buyers ask
Where is Wailea Fairway Villas located?
Wailea Fairway Villas sits at 3950 Kalai Waa Street, along the golf course in the northern part of Wailea.
How big is Wailea Fairway Villas and when was it built?
Built in 1998, it holds 118 homes across 24 two-story buildings on just over 12 acres.
Is Wailea Fairway Villas set up for short-term rental?
No. Available records show vacation rental is not permitted here, and 75% of units are owner-occupied, making it one of Wailea's more residential communities.
Current listings at Wailea Fairway Villas
Live MLS search, pre-filtered to Wailea Fairway Villas. Press Search inside the box to see current listings.