This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.

Welcome to your elevated island escape at The Windsor Waikiki, where iconic views of Diamond Head meet sweeping Pacific panoramas — all from the 43rd floor.

This high-floor Waikiki Diamond Head view condo offers rare ocean and mountain views, making it an ideal 2-bedroom Waikiki monthly rental for guests seeking a luxury 30-day stay with parking, pool access, and remote-work-friendly amenities.

As a Hawaii property manager with 20 years of experience, I can tell you: high-floor Diamond Head view homes at The Windsor are rarely available for extended stays.

This beautifully curated two-bedroom, two-bathroom residence delivers the perfect blend of luxury and livability — ideal for extended vacations, couples traveling together, families, or remote workers craving a true work-from-paradise setup.

Perfect for guests searching for a Waikiki long-term stay, Waikiki 30-day rental, or Waikiki remote work rental.
Inside Your Island Retreat

From the moment you walk in, you’ll feel the thoughtful design. Plush pillows, layered blankets, chic décor, and stylish furnishings create a warm, boutique-hotel atmosphere — modern yet inviting.

Living & Dining

-Open living area framed by breathtaking ocean views

-Sofa sleeper for additional guests or cozy movie nights

-Dining area with a view — perfect for sunset dinners

Kitchen

-Fully equipped kitchen with modern appliances

-Everything needed to prepare meals at home

-Bedrooms & Baths

Both bedrooms feature private ensuite bathrooms, offering excellent privacy and comfort. Expect quality linens, soft lighting, and peaceful spaces designed for deep rest after long beach days.

One bedroom also includes a dedicated workspace, creating a quiet and convenient setup for guests seeking a Waikiki condo for remote work.

In-Unit Amenities

-Washer & dryer

-High-speed 1 Gig Wi-Fi

-65” TVs with cable and streaming apps

-Air conditioning in every room

-Bidets in both bathrooms

-Reserved parking stall (a rare Waikiki condo with parking!)

-Resort-Style Amenities

-Enjoy full access to The Windsor’s resident amenities:

-Swimming pool & Jacuzzi

-BBQ area

-Fitness center

Rooftop Sky Terrace with sweeping views of Waikiki — perfect for sunsets and even watching Friday night fireworks from Hilton Hawaiian Village

This Waikiki condo with pool, hot tub, fitness center, elevator access, and rooftop Sky Terrace offers true resort-style living.

Prime Yet Peaceful Location

Situated on the quieter, more residential side of Waikiki, you’ll enjoy peaceful evenings at home — with vibrant Waikiki just minutes away.

Nearby highlights include:

-Ala Moana Beach Park (walkable beach access)

-Ala Moana Center

-Hawaii Convention Center

-Waikiki Beach

-Beaches, world-class dining, shopping, and nightlife

An ideal Waikiki condo near Ala Moana Beach Park for guests seeking a quiet residential area with easy access to Waikiki attractions.

This property is new to our inventory — reviews are on the way! Rest assured, it has been carefully prepared to deliver a wonderful guest experience.

Aliʻi Beach Rentals is a full-service professional vacation rental company with in-house maintenance, dedicated cleaning teams, and experienced property managers right here in Waikiki. Our local office is available 24/7 for emergencies, so you can relax knowing you’re well cared for.

Whether you’re here for ocean views, beach days, glowing sunsets, or a comfortable extended stay in paradise, this high-floor Windsor Waikiki condo promises an unforgettable experience.

We look forward to welcoming you to your Hawaii home away from home.