The Great Mahele Impact (1848): The Great Mahele of 1848 divided all Hawaiian lands among King Kamehameha III, the government, and a few ali'i. This historic land division set the foundation for individual ownership and, crucially, established the land tenure patterns that would later create Waikiki's complex leasehold system. Much of Waikiki's land was granted to Princess Bernice Pauahi Bishop, whose estate would become the Bishop Estate/Kamehameha Schools - still the largest private landowner in Hawaii.
Early Tourism Development (1880s-1920s): Hawaii's first hotel opened in Waikiki in 1837, with the famous Moana Hotel (now Moana Surfrider) following in 1901, billing itself as "The First Lady of Waikiki." A pivotal change came in the 1860s when the government expanded the path from Honolulu into a full road, making travel much easier and spurring the release of lots next to Kapiolani Park in 1883.
The Mosquito Solution & Canal Creation (1928): The completion of the Ala Wai Canal in 1928 was transformative, draining the mosquito-infested wetlands and creating developable land. The reclaimed land was divided into 5,000 square foot lots and sold, establishing the Waikiki layout we know today. This artificial boundary also created an enforced separation from neighboring areas, establishing Waikiki's distinct identity.
Zoning Evolution: The Waikiki Special District (WSD)
1960s-1970s Building Boom: The vast majority of Waikiki's condominiums date from the 1960s and 1970s, when the low-rise, single-family landscape was transformed into the forest of high-rises visible today. During this unprecedented build-up, buildings were often massive and bulky, with floorplates extending to property lines, overlooking open spaces and appropriate urban design in favor of maximizing developable floor area.
Creation of the WSD (1976): Community concern over Waikiki's transformation from a laid-back tropical resort to a dense, high-rise urban center led to the creation of the Waikiki Special District in 1976. This unique zoning framework established standards limiting the location of permitted uses and building form (height, density, setbacks, and open space).
Nonconforming Use Legacy: A key characteristic of modern Waikiki is its high degree of nonconformities created by the 1976 zoning:
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- Fully one-half of all hotel establishments in Waikiki are nonconforming uses
- Approximately 52% of buildings have too much floor area
- More than 90% of buildings are nonconforming structures for various reasons
WSD Reforms (1995-2011): Multiple task forces have worked to modernize the WSD, with the Waikiki Improvement Association leading efforts in 2011 for the third round of reforms, rezoning Waikiki for more mixed-use flexibility and relaxing restrictions on small lot development and sidewalk dining.
Short-Term Rental Regulations: A Complex Legal Landscape
Current Legal Framework: The regulation of short-term rentals (STRs) in Waikiki has undergone dramatic changes, creating a complex legal environment that potential investors and residents must navigate carefully.
2019 Foundation (Ordinance 19-18): Bill 89 became law as Ordinance 19-18 in June 2019, establishing that short-term rentals outside resort/resort mixed-use districts are prohibited unless the property has a Non-Conforming Use Certificate (NUC). Only 1,699 owner-occupied, hosted B&Bs were to be permitted outside resort zones.
2022 Stricter Rules (Bill 41/CO 22-7): In April 2022, Mayor Blangiardi signed Bill 41 into law, implementing three significant changes:
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- 90-Day Minimum: Rental terms less than 90 days (formerly 30 days) in residential neighborhoods became illegal
- Registration Requirements: STR properties with rental terms under 90 days must register with a $1,000 initial fee and $500 annual renewal
- Waikiki Exceptions: Waikiki Banyan and Waikiki Sunset units became legal STRs, even without NUCs
Legal Challenge & Current Status: The Hawaii Legal Short-Term Rental Alliance successfully challenged the 90-day minimum. In October 2022, U.S. District Court Judge Derrick K. Watson granted a permanent injunction, allowing existing STRs to continue operating with a 30-day minimum, provided they opened before the 2022 ordinance.
Where STRs Are Legal:
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- Resort-zoned areas: Primarily Waikiki, Ko Olina, and Turtle Bay Resort
- Grandfathered properties: Existing STRs that operated before 2022 ordinance
- Specific exempted buildings: Waikiki Banyan and Waikiki Sunset
Tax Implications: STR operators must navigate complex tax requirements:
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- State and county Transient Accommodations Tax (TAT)
- General Excise Tax (GET)
- Property taxes at Transient Vacation or Hotel & Resort rates
- Platforms like Airbnb cannot collect taxes in Hawaii - operators must handle all obligations
Leasehold vs. Fee Simple: Understanding Land Ownership
The Bishop Estate Legacy: A unique aspect of Waikiki real estate is the prevalence of leasehold properties, where buyers purchase the building but lease the land from Kamehameha Schools (formerly Bishop Estate). Princess Bernice Pauahi Bishop's estate includes ownership of substantial portions of Waikiki, meaning many hotels and condominiums sit on leased land.
Current Leasehold Landscape:
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- About 10% of Oahu condos are leasehold, with many concentrated in Waikiki
- 14 buildings in Waikiki have land leases expiring between 2024 and 2054
- Most leasehold properties are concentrated in Waikiki, Downtown, Makiki, and University areas
- As of 2023, 445 leasehold condos changed hands in one year alone
Leasehold Considerations:
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- Lower Purchase Prices: Often 50% less than equivalent fee simple properties
- Financing Challenges: Banks require lease terms of at least 35 years for 30-year mortgages
- Declining Values: Property values typically decrease as lease expiration approaches
- Lease Rent Changes: Can adjust every 10-20 years depending on lease terms
- Extension Possibilities: Kamehameha Schools often extends leases, particularly for well-maintained properties
Investment Considerations: Leasehold properties may appeal to:
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- Investors seeking lower entry costs and immediate cash flow
- Lifestyle buyers wanting luxury at reduced prices
- Groups purchasing shared vacation properties
- Those seeking short-term Hawaii experiences rather than long-term equity building
Board Structure & Meetings:
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- Meeting Schedule: Second Tuesday of every month at 6:00 PM
- Location: Waikiki Community Center, 310 Paoakalani Avenue
- Composition: 17-member board requiring 9 members for quorum
- Public Access: Meetings broadcast on Olelo Channel 49 and available online
Board Responsibilities:
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- Advisory capacity for state and City & County of Honolulu
- Pass resolutions reflecting community consensus
- Review development projects and liquor licenses
- Address citizen concerns and public events
- Coordinate with city departments and officials
Recent Focus Areas:
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- Transportation management and traffic flow improvements
- Public safety initiatives and street closure policies
- Commercial event impacts on the community
- Beach maintenance and improvement projects
- Short-term rental enforcement and community concerns
Community Involvement: New residents are encouraged to attend meetings to:
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- Understand local issues and development projects
- Voice concerns about neighborhood impacts
- Learn about upcoming public events and street closures
- Connect with longtime residents and community leaders
- Participate in shaping Waikiki's future development
Major Attractions & Amenities
Beaches (8 distinct areas):
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- Fort DeRussy Beach, Duke Kahanamoku Beach, Halekulani Beach
- Royal Hawaiian Beach, Kūhiō Beach, Kapiʻolani Beach
- Queens Beach, and Kaimana Beach
- Nearly 2.8 million cubic feet of sand have been added since 1951
Parks & Recreation:
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- Kapiolani Park: 300-acre park featuring Honolulu Zoo, Waikiki Aquarium, and Waikiki Shell
- Fort DeRussy: Military recreation area with beach access
- Ala Wai Harbor: Yacht harbor and recreational boating
Shopping & Dining:
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- Kalakaua Avenue: Known as the "Pacific's Rodeo Drive" with luxury retailers
- Royal Hawaiian Center: Premier shopping destination
- International Marketplace: Open-air shopping and dining complex
- Hundreds of restaurants representing global cuisines
Transportation & Connectivity
- Downtown Honolulu: 4.5 miles / 10-15 minutes
- Honolulu Airport: 9.8 miles / 20-30 minutes
- Diamond Head: Adjacent / 5 minutes
- Ala Moana Center: 2 miles / 10 minutes
- TheBus: Comprehensive public transit connections
- Waikiki Trolley: Tourist-oriented transportation system
Investment & Living Considerations
Market Characteristics:
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- High-density urban resort environment
- Mix of hotel, residential, and mixed-use properties
- Strong rental demand from both tourists and local workforce
- Complex zoning and land tenure requiring professional guidance
Lifestyle Factors:
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- 24/7 resort atmosphere with constant activity
- Tourist-oriented services and amenities
- Limited parking and high-density living
- Proximity to beaches, shopping, and dining
- Year-round warm weather and ocean activities
Notable Waikiki Properties & Buildings
Understanding the specific buildings and their characteristics is crucial for both residents and investors in Waikiki. Each property offers unique features, price points, and investment opportunities:
Ultra-Luxury Properties
Ka La'i Waikiki Beach (Formerly Trump Tower Waikiki)
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- Address: 223 Saratoga Road
- Built: 2009, 38 floors, 469 units
- Unit Types: Studios to 3-bedroom penthouses ($530,000-$9.98M range)
- Recent Transformation: Now operated by Hilton's LXR Hotels & Resorts
- Amenities: Infinity pool, spa, fitness center, three high-end restaurants, valet parking
- Investment Notes: Building undergoing major renovations (2025-2026) with special assessments; fully furnished units with hotel rental program options
- Unique Features: Most units have ocean views due to architecture and lanai angles; cross-street from Fort DeRussy Beach
The Ritz-Carlton Residences, Waikiki Beach
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- Address: 383 Kalaimoku Street (Two Towers)
- Built: 2016-2018, dual 38-story towers
- Total Units: 552 residences (307 in Ewa Tower, 245 in Diamond Head Tower)
- Unit Types: Studios to 4-bedroom penthouses ($910,000-$20M+ range)
- Amenities: Two infinity pools, full-service spa, fitness center, yoga studio, theater room, valet service, concierge
- Dining: Sushi Sho, La Vie, Dean & DeLuca on-site
- Investment Notes: Fee simple ownership, hotel rental program available, comprehensive hospitality services
- Unique Features: Located adjacent to "Luxury Row" shopping; all ocean-facing residences
Beachfront & Prime Location Properties (Across the street from Waikiki Beach)
Waikiki Shore - ONLY Beachfront Condotel
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- Address: 2161 Kalia Road
- Distinction: ONLY true condominium directly on Waikiki Beach
- Built: 1960 Older low-rise building with unique beachfront positioning the only condo directly on Waikiki Beach with 50 linear feet of frontage
- Amenities: Direct beach access via special gate, beach shower facilities
- Investment Notes: No on-site amenities but benefits from adjacent Fort DeRussy Beach Park facilities
- Unique Features: Built perpendicular to beach for optimal trade wind exposure; '00' stack units are most sought-after oceanfront
- Zoning: X6 Resort Hotel Precinct
Waikiki Beach Tower - Across the Kalakaua rom the beach
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- Address: 2470 Kalakaua Avenue
- Unit Types: All 2-bedroom, 2-bathroom units
- Land Tenure: Mix of fee simple and leasehold (leases expire 2039)
- Amenities: Resort zoning allows vacation rentals, managed by Aston Hotels
- View Considerations: Most units have ocean views; lower floors may have obstructions; '04' stack views open up above 16th-17th floors
- Investment Notes: Four units per floor; can participate in condotel rental pool
- Zoning: X6 Resort Hotel Precinct
Historical & Iconic Properties
Rosalei - The Pioneer (1955) - Not STR Legal
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- Address: 445 Kaiolu Street
- Historical Significance: The first residential coop high-rise in Waikiki, built in 1955 at 12 stories - even before statehood
- Unit Types: Studios (407 sq ft) and 1-bedrooms (456-503 sq ft), $229,000-$325,000 range
- Investment Notes: Secured building with community laundry, swimming pool, maintenance fees include electricity, water/sewer, internet and cable
Kalia - Hidden Garden Sanctuary (1958-1960) - Not STR Legal
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- Address: 425 Kalia Road
- Historical Significance: Built 1958-1960, among earliest high-rise developments alongside Rosalei, representing early development for local working and middle class
- Unit Types: "A residence few probably even know exists, despite its size" with 303 units in three leasehold buildings
- Investment Notes: Leasehold with lease expiring in 2048, $95,000-$168,000 price range
Ilikai Apartment Building - Legal STR
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- Address: 1777 Ala Moana Boulevard
- Historical Significance: Introduced the "condotel" concept to Hawaii in 1964
- Fame: Featured in original "Hawaii Five-O" opening credits
- Unit Types: Studios to 3-bedroom condos
- Amenities: Pool, restaurants, central Waikiki location
- Investment Notes: Iconic status maintains strong rental demand; variety of price points available
- Location Advantage: Close to Ala Moana Beach Park and Ala Moana Center
- Zoning: X6 Resort Hotel Precinct
Waikiki Grand Hotel - Legal STR
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- Address: 134 Kapahulu Ave
- Historical Significance: Built 1963
- Unit Types: 219 units, mostly studios between 195 adn 365 sqft, directly across from Honolulu Zoo
- Amenities: Legal STR with rooftop deck offering ocean views and a pool and features Hula's Bar & Lei Stand on 2nd floor with Kapiolani Park views
- Location Advantage: "Within 134 steps of the famous white sand beach"
- Zoning: X6 Resort Hotel Precinct
Mid-Range Investment Properties - Legal STR
Waikiki Banyan & Waikiki Sunset
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- Address: 201 Ohua Avenue & 229 Paokalani Ave
- Built: Twin towers, 6th floor amenity deck
- Unit Types: Studios to 2-bedroom units
- STR Status: All units now legal for short-term rentals under Bill 41 exemption
- Amenities: Pool, fitness center, BBQ area, 24-hour security
- Current Issues: 6th floor amenity deck closed for spalling repairs; special assessments through December 2025
- Investment Notes: Walking distance to International Market Place and Royal Hawaiian Shopping Center
- Management: Available through Aston Hotel rental program
- Air Conditionaing: Waikiki Banyan has window AC and the Waikiki Sunset has central AC and is a true 1 bedroom
- All have a full kitchen and 1 parking stall unassisgned
- Architect: Maruice Kondo of INK Architects was responsible for 3700 plus units, including The Pearl One and Two, Craigside One and Two, Waikiki Banyan, Waikiki Sunset, Honolulu Tower, Hale Kaheka and the Queen Victoria Residences.
Marine Surf Waikiki
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- Address: 364 Seaside Ave
- Unit Types: Built in 1968 224 Studios on 24 floors 392 sqft, 2 stacksk have 2 lanais. The Penthouse level: 1-bedroom units (772-858 sq ft)
- Price Range: Affordable entry point for Waikiki ownership
- Amenities: Pool, fitness center, hot tub, BBQ area, 24-hour security, on-site restaurant and shops
- STR Legal: Resort zoning allows daily rentals
- Investment Performance: Units generating $50,000+ annually in rental income
- Location: Walking distance to Waikiki Beach, convenient to transportation
- Land Tenure: Fee Simple
- Building Amenities: Pool on property, community laundry, 2 secure elevators, 2 restaurants
- Zoning: X6 Resort Hotel Precinct
- Historical Context: The Marine Surf Waikiki was built during the peak period of Waikiki's high-rise development. The late 1960s was when "the joke about the construction crane being the Hawaii State Bird was first heard," reflecting the massive construction boom occurring in Waikiki at that time. This period saw Waikiki become "unrecognizable" as "the once plentiful houses between the Ala Wai and Kuhio Avenue disappeared almost completely" and "high-rises occupied almost every lot".
Residential-Focused Properties
Quiet East End (Near Kapiolani Park & Zoo)
Parkview
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- Address: 240 Makee Road
- Built: 1967, 13 floors, boutique building
- Unit Types: 1-bedroom units, plus larger penthouse A & B units
- Land Tenure: Mix of fee simple and leasehold (leasehold expires 2045)
- Views: Many units overlook Kapiolani Park with Diamond Head views
- Amenities: Swimming pool, glass railing upgrades for modern look
- Resident Appeal: Quiet location near Honolulu Zoo, several blocks from beach
- Price Range: $425,000-$950,000 depending on floor and land tenure
Liliuokalani Gardens
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- Distinctive Features: Resort-style living with lush tropical grounds
- Amenities: Koi fish swimming through waterways, walking paths over bridges
- Recreation: Swimming pool, spa, cabana, BBQ areas, tennis courts, garden areas
- Unit Types: 1-bedroom options in Queen Tower and other configurations
- Upgrades: Properties with waterproof laminate flooring, granite countertops
- Atmosphere: Tropical resort feel within residential building
Central Waikiki (Mid-Area Living)
Waikiki Park Heights
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- Address: 2440 Kuhio Avenue
- Built: 1974, 24 floors, 268 units
- Unit Types: 1 & 3-bedroom units
- Residential Focus: No short-term vacation renting allowed
- Amenities: Pool, recreation deck, community laundry, on-site manager
- Special Features: Set back from Kuhio Avenue with covered driveway (reduced noise)
- Dining: Hy's Steakhouse at ground level
- Resident Appeal: Security, quiet location despite central positioning
Ala Wai Palms
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- Address: Along Ala Wai Boulevard
- Built: 1961 (first year of condo law in Hawaii)
- Historical Significance: One of Hawaii's earliest condominiums
- Location: Ala Wai Canal frontage
- Character: Older building with historical charm
- Resident Appeal: Canal views, established neighborhood
Seaside Towers Building Details
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- Address: 435 Seaside Avenue, Honolulu, HI 96815
- Year Built: 1962
- Architect: E.L. Bauer & Developer: Sea Side Development Inc
- Building Specifications: 126 units, 15 floors All 1-bedroom/1-bathroom units
- Views: Views of the Ala Wai Canal, golf course, Koolau Mountains, and Waikiki's city lights
- Lanais: Units do not have lanais
- Building Amenities: Swimming pool, BBQ area, surfboard storage, Storage lockers that are deeded to the units
- Character: Lobby features a classic lava rock wall from the 60's
- Special Features: Set back from the street with a garden-lined entry path, just 2½ to 3 blocks from the Royal Hawaiian Hotel's beachfront
Hale Moani
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- Unit Types: 1-bedroom, 1-bathroom condos with wrap-around lanais
- Features: Corner units with expansive lanais, natural light, trade wind exposure
- Views: Partial city and mountain views
- Security: Secured building with fob entry and elevator access
- Parking: Reserved parking stalls included
- Location: Blocks from Waikiki Beach and Ala Wai Canal
West End (Near Ala Wai Canal & Ala Moana)
Marina Towers
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- Address: 1645 Ala Wai Boulevard
- Built: 1967, 15 floors, single tower
- Unit Types: Primarily 2-bedroom, some 3-4 bedroom penthouses on 15th floor
- Modernization: Glass railings added for sleek, modern appearance
- Views: Nice Ala Wai Canal and marina views
- Amenities: Heated saltwater pool, BBQ area
- Parking: Only 1 stall per unit regardless of size
- Resident Appeal: Low maintenance fees, canal views, quieter end of Waikiki
Canterbury Place
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- Address: 1910 Ala Moana Boulevard
- Built: 1978, developed by Bruce Stark
- Complex Ownership: Mix of fee simple, leasehold, and sandwich lease units
- Layout: "A" stacks face ocean, "B-D" stacks face Fort DeRussy
- Amenities: Swimming pool, hot tub, sauna, tennis court, secured building
- Features: Porte cochère for pickup/drop-offs
- Views: Spectacular Diamond Head and ocean views available
- Price Range: $828,000-$1.1M+ depending on floor and view
Residential Living Considerations by Area
East End Benefits (Near Zoo/Park):
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- Quieter, more residential atmosphere
- Close to Kapiolani Park's 300 acres of green space
- Walking distance to Honolulu Zoo and Waikiki Aquarium
- Near trendy Monsarrat Avenue dining and shopping
- Less tourist congestion than central Waikiki
Central Waikiki Benefits:
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- Heart of the action with immediate access to beaches
- Walking distance to major shopping and dining
- Best public transportation connections
- Full resort amenities and services nearby
West End Benefits (Ala Wai Area):
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- Canal and mountain views instead of ocean crowds
- Closer to Ala Moana Center for serious shopping
- More affordable than beachfront locations
- Better parking availability
- Quieter than tourist-heavy areas
Building-Specific Considerations for Residents
Short-Term Rental Policies: Verify building policies - some buildings like Waikiki Park Heights prohibit STRs, creating quieter residential environments
Amenities vs. Fees: Newer luxury buildings have extensive amenities but higher fees; older buildings often have lower fees but fewer amenities
Tourist Impact: Buildings closer to beach and major hotels experience more tourist activity; Ala Wai buildings typically have more resident-focused communities
Parking: Critical consideration - some buildings offer only one stall regardless of unit size; monthly parking nearby ranges $175-250+
Land Tenure: Always verify fee simple vs. leasehold status and remaining lease terms for financing and long-term value considerations
Luxury High-Rise Options
Allure Waikiki
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- Modern high-rise: Contemporary amenities and design
- Unit Types: Studios to multi-bedroom residences
- Amenities: Modern fitness facilities, pool, business center
- Investment Notes: Completed in 2010 with updated building systems
- Address: 1837 Kalakaua Ave, Honolulu, HI 96815
The Watermark Waikiki
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- Modern luxury high-rise: Contemporary amenities and design completed in summer 2008, offering a luxury resort-like experience
- Unit Types: 2-3 bedroom residences, with most condos being 2 bed, 2 bath units, however there are some nice 3 bed units found in the '05 stacks
- Amenities: Infinity Pool, Hot Tub, Gym, Sauna, BBQ Pavilion, 5-BBQ settings, Media Room/Library; heated swimming pool, Jacuzzi, sauna, BBQ area, fitness room, floor to ceiling windows, gourmet kitchens, soaker tubs, concierge, and 24-hour security
- Investment Notes: Built in 2008 by developer Intracorp, 196 units, 38 floors; designed with Guerin Glass Architects, Architects Hawaii, and Philpotts & Associates; spans a 4-acre lot with 60% open space, including a 1-acre landscaped garden with walking paths; short-term vacation renting not allowed
- Address: 1551 Ala Wai Blvd, Honolulu, HI 96815
- Unique Features: Open-air lobby features stone flooring and tropical gardens, staffed by a professional concierge team; most units have lanais attached, with some as big as 225 sq ft
- Views: Corner units have 180 degree views, with East side offering sunrise and Diamond Head views, West side offering Hawaii sunsets over West Oahu
- Setting: 13,800 sq ft public park on Hobron Lane, enhancing the pedestrian experience with deep setbacks (22.5-36 ft) and wide sidewalks
