Sleepy Hollow
1667 S Kihei Rd, Kihei, HI 96753
Sleepy Hollow is an unusual layout for South Kihei Road: instead of one shared building, it is 11 separate single-story structures on a fee-simple parcel, built in 1980. Ten of the eleven units share the same three-bedroom, two-bath, 960-square-foot floor plan, so it reads more like a small cluster of detached homes than a typical condo complex. There is no shared amenity package listed here and the property is not on the water, which fits its inland setting away from the beachfront buildings that line the coast.
Available records describe Sleepy Hollow's zoning as R-2, and both vacation rental and long-term rental are reported as allowed, which is a straightforward, flexible position for a fee-simple property of this size. Because it sits outside the county's apartment- and hotel-zoning categories used to build the Bill 9 phase-out list, Minatoya-list questions don't really apply here the way they do at oceanfront apartment buildings. Still, confirm current rules with Diane before you count on either rental strategy.
The short version
- ✦11 separate single-story structures rather than one shared building
- ✦10 of 11 units share a 3 BR / 2 BA, 960 sq ft floor plan
- ✦Built in 1980 on a fee-simple, R-2 zoned parcel
- ✦Not on the water, set back from Kihei's beachfront buildings
- ✦Both vacation rental and long-term rental reported as allowed
By the numbers
- Year built
- 1980
- Total units
- 11
- Buildings
- 11 (1-story)
- Floor plans
- 3 BR
- Unit size
- 960 sq ft
- Pets
- Pet-friendly
Short-term rental status
Available records describe Sleepy Hollow's zoning as R-2, fee simple, with both vacation rental and long-term rental reported as allowed. Since R-2 sits outside the apartment- and hotel-zoning categories that feed Maui County's Minatoya list and Bill 9 phase-out, those specific restrictions aren't expected to apply here in the same way they do at oceanfront apartment-zoned buildings. Confirm current rules with Diane before counting on rental income.
Rules are actively changing as of 2026. Contact Diane for the current status of a specific unit.
Layouts
Three bedroom
3 bd · 2 ba · 960 sq ft
Questions buyers ask
Where is Sleepy Hollow located?
Sleepy Hollow is at 1667 S Kihei Road, set back from the beachfront buildings that line the coast in this part of Kihei.
What kind of building layout does Sleepy Hollow have?
It's unusual for the area: 11 separate single-story structures rather than one shared building, built in 1980. Ten of the eleven units share the same three-bedroom, two-bath, 960 square foot floor plan.
Can you do short-term rental at Sleepy Hollow?
Records describe R-2, fee-simple zoning with both vacation rental and long-term rental reported as allowed. R-2 sits outside the categories that feed the county's Minatoya list and Bill 9 phase-out, so those specific restrictions aren't expected to apply here, but confirm current rules with Diane before counting on rental income.
Current listings at Sleepy Hollow
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