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Windward · Oahu

Kailua and Waimanalo

Kailua is the largest town on Oahu’s windward side, with beachfront neighborhoods including Lanikai. Waimanalo, to the south, is a smaller rural community along the coast.

Mostly houses4 condo complexesHawaiian Home Lands in this area

About Kailua and Waimanalo

Kailua’s single-family median was $1,735,000 over the 12 months through September 2026, on 269 sales, up 11%. Homes sold in a median of 16 days.

Condos are limited, mostly townhomes and low-rise buildings near Kailua town, with 97 sales at a median of $770,000.

Nearby base: Marine Corps Base Hawaii, Kaneohe Bay.

What homes sell for

Property typeSales, Oct 2025–Sep 202612-month median
Single-family homes269$1.74M
Condos97$770K

Figures are for the MLS Kailua region.

Source: Locations Hawaii analysis of Oahu MLS sales for the 12 months through September 2026 (published October 5, 2026). Oahu figures are 12-month medians by MLS region, which are steadier than single-month numbers. Region boundaries don’t always match neighborhood names exactly.

Can you rent to visitors?

HousesNightly only in resort zonesOn Oahu, renting a house or condo for less than 30 days is illegal outside the resort districts (Waikiki’s resort precinct, Ko Olina and Turtle Bay) unless the property holds a nonconforming use certificate. The city’s 2022 ordinance (Ordinance 22-7) raised the residential minimum to 90 days. A federal court blocked that change for rentals of 30 to 89 days that were already lawfully operating, but anyone starting a rental now should plan on 90 days or more and confirm with the Department of Planning and Permitting.
CondosVaries by buildingIn our directory: 4 90+ days only. Visitor rental rules are set building by building by zoning and house rules. Our directory shows each building’s status. See the Oahu condo directory.

Land, title and what to check

Waimanalo includes a large Department of Hawaiian Home Lands homestead. DHHL awarded 400 project leases for Waimanalo in July 2026.

Hawaiian Home Lands homesteads are leased rather than sold on the open market. Leases run 99 years and are awarded from the Department of Hawaiian Home Lands waiting list to native Hawaiians with at least 50% Hawaiian ancestry. A lease can pass only to a qualified relative or another eligible beneficiary, so these homes don’t appear as regular listings.

Hazards, water and access

Check any address for its FEMA flood zone, tsunami evacuation zone, sea level rise exposure, lava zone and wildfire risk with our Hawaii flood zone lookup.

Public schools

The public high school for most addresses here is Kailua or Kalaheo High School, depending on address. Assignments go by address, so confirm with the Hawaii State Department of Education.

Condo complexes in Kailua and Waimanalo

Units, year built and visitor rental status from our Oahu condo directory.

Hale MakaleiKailua · Kailua24 · 199590+ days onlyHokulani in KailuaKailua · Kailua144 · 198990+ days onlyKa Malanai at KailuaKailua · Kailua153 · 201490+ days onlyWindward PassageKailua · Kailua203 · 197990+ days only

Sources: Locations Hawaii: Oahu residential market, September 2026; Title Guaranty Hawaii monthly Oahu sales reports; Honolulu Ordinance 22-7 court ruling (VRMA); City and County of Honolulu: FEMA flood map update; Skyline (Honolulu rail); DHHL Oahu lease awards, July 2026; HBR: Ordinance 25-44 tax tiers. Checked October 2026. This guide sticks to public facts about prices, rules, land and hazards. It doesn’t rate neighborhoods or describe who lives in them.