Short-Term Rentals (STR) Priced Between 2000000-3999999

2 Beds ⋅ 2 Baths ⋅ 202613745 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 DOM ⋅ Waikiki Beach Tower BLDG.

Legal nightly rental in one of Waikiki’s most sought-after towers! This beautifully renovated (2025) 2-bedroom, 2-bathroom fee simple residence at Waikiki Beach Tower spans 1,263 sq ft on the 20th floor — one of only 4 units per floor in this desirable stack — offering breathtaking ocean and coastline views. Enjoy resort-style living steps from world-famous Waikiki Beach, with the flexibility to live in, rent long-term, or operate as a legal short-term rental for maximum investment return. Building amenities include, BBQ Gym, Pool, whirlpool, 24-hr security and valet parking. One assigned covered parking. Convenient Location, right across to world famous Waikiki Beach, shops and restaurants. In the neighborhood, the Honolulu Zoo, Waikiki aquarium, Kuhio Beach, and Kapiolani Park. This is a rare opportunity in a building with limited STR-eligible inventory. Don’t miss this one!

2470 Kalakaua Avenue Unit 2004, Honolulu

$2,300,000

2 Beds ⋅ 2 Baths ⋅ 202612191 MLS ⋅ FS - Fee Simple Tenure ⋅ 28 DOM ⋅ The Ritz-Carlton Residences - 383 Kalaimoku BLDG.

Enjoy luxury living at higher floor, ocean view unit at The Ritz-Carlton Residences Waikiki Beach Tower 1 Hotel/Condo! This 2 Bedrooms comes fully furnished with all linens & kitchenware. Amenities include infinity pool, concierge, valet parking, and a full service spa. Other fee is monthly reserve fund assessment.

383 Kalaimoku Street Unit 3107, Honolulu

$2,750,000

2 Beds ⋅ 2 Baths ⋅ 202612229 MLS ⋅ FS - Fee Simple Tenure ⋅ 35 DOM ⋅ Waikiki Beach Tower BLDG.

Experience true beachfront living at this highly sought after Waikiki Beach Tower '01 stack. This is a legal short term rental building with a great hotel program or ability to Airbnb it yourself. This fully renovated, 2-bedroom, 2-bath unit offers approximately 1,150 sq. ft. of interior living space with a large lanai showcasing breathtaking panoramic ocean and sunset views. Designed for both comfort and convenience, this turn key fully furnished unit features a full kitchen, in unit washer and dryer, and an open layout that seamlessly blends indoor and outdoor island living. With only four units per floor and dual elevators, enjoy enhanced privacy and exclusivity. Located directly across from world-famous Waikiki Beach, this luxury condo hotel offers resort-style amenities including a heated pool, jacuzzi, fitness center, BBQ cabanas, lounge areas, and 24-hour valet and concierge service. Don’t miss this rare opportunity to own a premier oceanfront property in the heart of Waikiki—just steps from sandy beaches, dining, shopping, and entertainment.

2470 Kalakaua Avenue Unit 1101, Honolulu

$2,000,000

2 Beds ⋅ 2 Baths ⋅ 202611918 MLS ⋅ FS - Fee Simple Tenure ⋅ 39 DOM ⋅ Trump Tower Waikiki BLDG.

Experience the pinnacle of coastal sophistication in this rare corner 2 bedroom 2 bathroom, situated on the prestigious 35th-floor Executive Level. Immerse yourself in soaring ceilings and floor-to-ceiling glass walls that frame breathtaking, unobstructed views of the Pacific Ocean, Fort DeRussy Park, and iconic Hawaiian sunsets. Residence features an expansive open-concept layout anchored by a gourmet kitchen that would satisfy any chef, boasting Wolf and Sub-Zero appliances, custom oak cabinetry, and elegant marble countertops, bespoke furnishings, and spa-inspired marble bathrooms. Following a multi-million dollar transformation into the Hilton LXR ultra-luxury brand, enjoy world-class amenities including a 24-hour concierge, infinity pool, sun deck, gym, meeting room, restaurants, cafe and the signature hospitality. This is more than a home, it is Waikiki’s most coveted address.

223 Saratoga Road Unit 3501, Honolulu

$2,650,000

2 Beds ⋅ 2 Baths ⋅ 202611252 MLS ⋅ FS - Fee Simple Tenure ⋅ 49 DOM ⋅ Waikiki Beach Tower BLDG.

Experience elevated island living in the highly sought-after “02” stack residence at the iconic Waikiki Beach Tower. Perfectly positioned along Waikiki’s world-famous shoreline, this fully furnished residence captures breathtaking direct views of the Pacific Ocean, Waikiki Beach, the coastline, and the sparkling city skyline. The spacious private lanai offers seamless indoor-outdoor living, ideal for relaxing or entertaining while enjoying the beauty of Waikiki. The open-concept layout flows effortlessly between the living, dining, and kitchen areas, creating an inviting space designed for comfortable island living. While the unit is not currently operated as a short-term vacation rental, Waikiki Beach Tower is located within resort zoning allowing legal short-term rental opportunities. Owners may choose to join the on-site Aston Hotel Rental Program, utilize an outside vacation rental management company, or simply enjoy the residence as a personal retreat in paradise.Current monthly dues include Maintenance Fees of $2,594.19, Capital Reserve Contributions of $371.34, and Easement Rent of $415.36.

2470 Kalakaua Avenue Unit 3102, Honolulu

$3,375,000

2 Beds ⋅ 2 Baths ⋅ 202611026 MLS ⋅ FS - Fee Simple Tenure ⋅ 52 DOM ⋅ Waikiki Shore BLDG.

Waikiki's ONLY true BEACHFRONT condo with LEGAL Daily Vacation Rentals. This rarely available 2 bdrm 2 bath residence at Waikiki Shore offers unobstructed Ocean, Beach, Sunset views from every room and a 37 ft lanai overlooking the Pacific. Wake up to surfers, Ocean breezes then enjoy front row seats to Waikiki's Friday Night fireworks. Fully furnished. Beautifully Updated. Move In Ready. Washer/Dryer too. Large storage next to unit. 24 /7 Security. Ideal Luxury 2nd home with effortless Lock & Leave ownership. Onsite rental program offers Income Potential. LOW HOA fees. Steps to World class dining, shopping and entertainment yet on the Beach. A Rare opportunity in Waikiki.

2161 Kalia Road Unit 402, Honolulu

$2,300,000

2 Beds ⋅ 2 Baths ⋅ 202610972 MLS ⋅ FS - Fee Simple Tenure ⋅ 54 DOM ⋅ Waikiki Shore BLDG.

Fully furnished corner unit in Waikiki Shore, Waikiki’s only true beachfront condominium and one of the few buildings allowing legal short-term vacation rentals. Extensively remodeled in 2017, this residence is in excellent condition and features a stylish kitchen and updated bathrooms. Split A/C systems, washer/dryer, microwave, oven, refrigerator, and motorized window coverings provide modern comfort and convenience. Living room furniture and kitchen bar stools were newly replaced in June 2026. Open the windows and enjoy refreshing trade winds and expansive views overlooking Fort DeRussy Park. Recent building improvements include new elevators installed in 2023 and a renovated lobby completed in late 2023. Just steps from the sandy beach, with the popular Steak Shack located on the ground floor, and within walking distance of Waikiki’s shopping, dining, and entertainment. Maintenance fee includes building maintenance fee $822.92, reserve contribution $183.25 and cable charge $65.09.

2161 Kalia Road Unit 418, Honolulu

$2,799,000

3 Beds ⋅ 3 Baths ⋅ 202610304 MLS ⋅ FS - Fee Simple Tenure ⋅ 54 DOM ⋅ Beachvillas@Ko Olina BLDG.

Discover "The Power of Beachvillas Vacation Rental". High-End luxury condominium on the beach can perform 6 nights minimum legal vacation rental in West Oahu, Hawaii is now within the reach. One of the largest 3 bedroom + 3 full bathroom unit at Beachvillas@Ko Olina sleeps 8 became available. Two covered parking stalls and a great size of the basement storage come with the unit which can provide the owner a great flexibility. The unit is well maintained and fully furnished perfectly for rental outsourcing or your vacation home. The owner can block it's desired multiple Hawaii vacation dates/weeks as you wish throughout the year as short as one night. Not typical hotel pool, this is very special place where you can manufacture rental weeks your way. The location of the unit is uniquely set on the second floor of the ocean tower facing toward to Ko Olina Lagoon beaches. 2026-2027 rental schedule already on the book is available to share. The high yield rental income performance history is also available upon request. The maintenance fee is truly worth it for a great Beachvilla operation team just like a luxury hotel.

92-104 Waialii Place Unit O215, Kapolei

$2,500,000

202610650 MLS ⋅ FS - Fee Simple Tenure ⋅ 57 DOM ⋅ Aloha Surf Hotel BLDG.

Rarely available 2,295 SF restaurant space in the heart of Waikiki located in the lobby of Aloha Surf Hotel. Also included TMK 1-2-6-021-016-0005 & 1-2-6-021-016-0007, the commercial condo spaces C5, C6, C7. Previous establishment had 150-person capacity, with full Liquor License till 2AM. Lots of window street frontage visibility with individual Restaurant signage on building. Pool-side enclosed lanai with two doors for hotel pool access. Drive up street loading area for delivery. Equipped dining area with tables, chairs, buffet serving station, and more. A block away from the heavily foot traffic, International Market Place. Minutes away from Ala Wai Golf Course and a few blocks away from Waikiki Beach.

444 Kanekapolei Street Unit C5 C6 C7, Honolulu

$3,199,000

3 Beds ⋅ 4 Baths ⋅ 202610457 MLS ⋅ FS - Fee Simple Tenure ⋅ 60 DOM ⋅ Trump Tower Waikiki BLDG.

Price Reduction!!! Experience elevated island living and urban lifestyle at Ka La'i Waikiki. This fully furnished, exceptional, three bedroom, three and a half bath residence offers breath taking, unobstructed views of Diamond Head, the blue Pacific Ocean, Waikiki and Beyond. This luxurious residence blends sophisticated designs with world-class hotel amenities, creating the perfect balance of comfort, elegance and convenience. It is further highlighted by a well appointed hallway, higher ceiling heights, two spacious ensuite bathrooms, remote controlled drapes and a separate laundry room. Resort amenities include a heated pool, whirlpool, fitness center, spa, on site dining, valet parking and concierge service. 5 Star rated hotel/condo providing convenient location, just minutes away from the beach, luxury shopping and an abundance of dining options. Make this your next home or home away from home in Paradise with the renowned service and prestige of Hilton's LXR and Resort brand.

223 Saratoga Road Unit 3710, Honolulu

$3,750,000

2 Beds ⋅ 2 Baths ⋅ 202609798 MLS ⋅ FS - Fee Simple Tenure ⋅ 60 DOM ⋅ Waikiki Shore BLDG.

A rare offering at Waikiki Shore, this residence features a true two-bedroom, two-bathroom layout. Fully enclosed bedrooms provide privacy and enhanced usability for both owners and guests. The unit has been beautifully remodeled with a clean, modern design and is offered as a turnkey opportunity. The layout is efficient and well-proportioned, with seamless flow between the living, dining, and kitchen areas. Waikiki Shore is one of the only beachfront condominiums in Waikiki with legal daily rentals, offering flexibility for personal use and income generation. Direct beach access and immediate proximity to Waikiki’s dining, shopping, and resort corridor support strong year-round demand. A differentiated opportunity in a highly sought-after beachfront location.

2161 Kalia Road Unit 502, Honolulu

$2,200,000

2 Beds ⋅ 2 Baths ⋅ 202608634 MLS ⋅ FS - Fee Simple Tenure ⋅ 77 DOM ⋅ The Ritz-Carlton Residences - 383 Kalaimoku BLDG.

Luxury living at Ritz-Carlton Waikiki. Ewa Tower - 2 bedroom with amazing ocean and city view. Fully furnished with upscale appliances and Washer & Dryer. Watch the sunset and Friday night fireworks. Renovation completed in 2025 so this unit IS ELIGIBLE to join hotel rental! The Seller requests closing date to be after October 1, 2026.

383 Kalaimoku Streets Unit E2903, Honolulu

Short-Term Rentals Priced Between $2,000,000-$3,999,999