Waikiki.

Fee simple means you own the building AND the land underneath it — same as standard residential ownership in most U.S. markets. Leasehold means you own the building (or your unit's share of it) but pay ground rent to the landowner, who continues to own the dirt. In Waikiki, many older buildings (1960s and 1970s towers) sit on land leased from outside owners — Kamehameha Schools, the Queen Liliuokalani Trust, Outrigger Hotels & Resorts, the Kosasa family / ABC Stores, and several private trusts. Lease terms remaining vary wildly. Leasehold units typically sell at a discount to comparable fee simple units, but the discount reflects real underwriting risk — lease term remaining, renegotiable ground rent, exit liquidity in the secondary market.

No — and assuming yes is the most common Waikiki underwriting mistake. Honolulu Bill 41 (passed 2022) tightened short-term rental rules across most of Oahu, requiring 90-day minimum rental terms in most zones. Waikiki's Resort District zoning preserves legal short-term rental in specific resort-zoned buildings — primarily the hotel-condo and resort-zoned residential towers. Apartment-zoned residential Waikiki buildings (and there are many) generally cannot host short-term rental. Always verify the specific building's zoning category and the unit's legal short-term rental eligibility before underwriting on STR cash flow.

Bill 41 is the 2022 Honolulu short-term rental ordinance that tightened rules island-wide. It generally requires 30–90 day minimum stays in most residential zones, preserving short-term rental primarily in resort-zoned areas of Waikiki (and a few other resort-zoned pockets). Bill 41 has been litigated and modified — the current state of enforcement and definitions has evolved since passage. If you're underwriting a Waikiki condo on STR potential, the building's specific zoning + Bill 41 compliance status is the diligence point that matters most.

A condotel (hotel-condo) is a building structured as condominium ownership where the units are managed by a hotel operator in a rental pool. Owners can choose to occupy their units or place them in the rental pool for short-term-rental income managed by the hotel. Hotel-condo examples in Waikiki: Trump International Hotel Waikiki, Aston Waikiki Beach Tower, Ilikai Apartments (Aqua/Marriott pool), Tradewinds. Hotel-condo financing is different from standard residential — many lenders won't finance them with conventional mortgages. Underwriting requires understanding the rental-pool economics (operator split, marketing fees, peak/off-peak occupancy, owner-use restrictions). Different asset class than a standard condo.

Effectively no. Waikiki is zoned almost exclusively for high-rise residential, hotel, mixed-use, and resort uses. If you want a single-family home in this area of Honolulu, look at Diamond Head, Kapahulu, or Kaimuki — adjacent neighborhoods with single-family inventory.

Many beach-block buildings (one block back from Kalakaua Avenue) have ocean views from upper floors. The premium beachfront-direct buildings (Waikiki Shore, Aston Waikiki Beach Tower, Waikiki Beach Tower, Ilikai Apartments) have unobstructed ocean views from most units. Interior Waikiki buildings — those on Kuhio Avenue and toward the Ala Wai Canal — typically have mountain or city views, with ocean views only from higher floors. View clarity is a building-specific question — verify the view from the actual unit before underwriting.

Highly building-dependent. Many older Waikiki buildings (especially leasehold towers) include zero or one parking space per unit. Newer luxury buildings (Ritz-Carlton Residences, Trump Waikiki, Allure) include one space, with second-space availability per unit varying. Some buildings have street parking only. Some have valet. Waikiki street parking is heavily metered and tourist-saturated — relying on it is rarely realistic. Always verify parking allocation per unit before offering.

Depends entirely on which Waikiki condo. A fee simple unit in a legal-STR-zoned building can be a strong investment vehicle with both equity appreciation and short-term-rental cash flow. A leasehold unit in a residential-only zone is a different proposition — limited appreciation runway, no STR income, lease term running down. A fee simple unit in a non-STR zone is a strong long-term hold but a weak income asset. The honest answer: Waikiki investment math has to start with the two structural questions (lease + zoning), not with the building's reputation or the listing photos.