Oahu Villas & Luxury Vacation Rentals

Luxury Villa Rentals for 2+ people

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Your Guide to Oahu Luxury Villas

Oahu is the third largest island in Hawaii, but it’s also the most populous. And while it’s home to iconic cultural centres like Waikiki and Honolulu on the South Side, it also has a quieter, more laidback North Shore and Leeward Coast, as well as a wilder Windward Coast. No matter where you stay on the island, though, Oahu luxury villas are the best way for groups to experience everything this beautiful part of Hawaii has to offer.

Oahu was first settled by the Polynesians over 1,000 years ago, with communities divided into tribes ruled over by chiefs. It was eventually brought into the Kingdom of Hawai’i by Kamehameha I in 1795, with Honolulu becoming the capital. The US annexed Hawaii in 1898, and it became the 50th state in 1959, leading to a major tourist boom for Oahu.

Today, Oahu remains the political and economic heart of Hawaii, but it’s also the center of the Hawaiian Renaissance, which seeks to revive and embrace native language, music, and culture. It’s also home to a wide variety of cities and communities, each with its own distinct vibe and landscapes.

Rental Escapes makes renting a luxury villa in Oahu easy. First, choose your travel dates. Next, select your party size. From there, your Rental Escapes Villa Specialist will happily present you with the best available Oahu luxury villas for your group. After, your Concierge customizes your trip, including transportation, chef service, excursions, boat charters, and more.

Luxury Villas Oahu

From beachfront estates to hillside retreats, luxury villas in Oahu are as varied as the island itself. They reflect the diversity, beauty, and culture that Oahu is known for, as well as Hawaii’s rich culture.

Oahu luxury villas can be found all across the island, including on the South Shore, near Waikiki and downtown Honolulu; on the Windward Coast, with its white-sand beaches and laid-back atmosphere; on the more rustic North Shore, with its world-famous surf culture; and on the West Side, with its championship golf and resort atmosphere.

No matter where you stay, expect features like private pools, sunset lanais, and tropical landscaping. Villas here focus on perfectly melding indoor and outdoor experiences, letting you enjoy Oahu’s famous landscapes and weather to the fullest.

Luxury Villas in Honolulu

Honolulu offers both a modern energy and a deep dive into Hawaiian history. Luxury villas in Honolulu let you experience this city’s vibrant culture while still having a beautiful retreat surrounded by lush landscapes. They include:

Ocean House: A true designer vision, Ocean House is a modernist masterpiece punctuated by stunning ocean views. It includes three ocean view suites, a downstairs gym, a gated entrance, and an indoor waterfall that adds an incredible ambiance. This is a villa that truly needs to be seen to be believed.

Banyan House: An iconic Hawaii villa at the foot of Diamond Head, Banyan House uses natural materials and a tropical atrium to create an unmatched ambiance. It also includes two lanais, stunning water features, billiards, exercise equipment, and more. A truly unique stay for up to 16 guests.

Oahu Villas on the Beach

Sitting directly on its pristine shores, Oahu villas on the beach offer the ultimate in relaxation. They include:

The Royal Hawaiian Estate: Located on beautiful Waimanalo Beach, where shows like Magnum PI, Hawaii 5-0, and Lost were filmed, the Royal Hawaiian Estate offers a rare chance to enjoy an area that does not allow hotels. Here you can take in spectacular views of both the ocean and the Ko’olau Mountains. There’s also a lush outdoor area with a lava rock waterfall, a large pool, a waterslide, Tiki torches, and more. Easily one of the best stays on the island.

Moana Vista: A waterfront villa nestled between Hauula and Punaluu on Oahu’s Northern Coast, Moana Vista is an elevated take on the traditional beach house. Relaxation abounds with your choice of hammocks, patio chairs, 3 beachfront hot tubs, a Polynesian kayak, and more. It also sits on one of the best snorkeling reefs on the island, and it’s all surrounded by a breathtaking tropical garden.

Oahu Luxury Villas in Waianae

If you’re looking for a more local and authentic part of Hawaii, then these Waianae villas on the Leeward side of the island are perfect:

Ocean Escape: A newly-constructed 3-bedroom villa, Ocean Escape offers both mountain and ocean views. Its open concept design affords a sense of space, and the viewing deck outside allows you to take in the spectacular sunsets.

Makaha Hideaway: Just 10 minutes from the beach, Makaha Hideaway allows you and your guests to connect. It sits on a corner lot, with large windows and plenty of natural light. Fun extras like games and beach gear make this a perfect choice for families.

Makaha Villa: A sunny 4-bedroom family villa, Makaha Villa sits on a cul-de-sac, ensuring a peaceful, quiet stay. Relax and enjoy the mountain views, or take a short drive to a beautiful beach. Plus, there’s a games room that the kids will love.

Oahu Luxury Villas FAQ

How to Travel to Oahu?

Most travelers will fly into Daniel K. Inouye International Airport in Honolulu. It’s Hawaii’s main airport, with plenty of nonstop and international flights. You can then use a rental car or a private transfer to get to your villa.
Your Rental Escapes Concierge can arrange airport transfers, rental cars, and any other transportation needs.

How to Get Around Oahu?

The best way to get around Oahu is by rental car. A rental car will let you see more of the island, providing easy access to beaches, hikes, and towns. That said, do be aware that there can be traffic in Honolulu, and parking in Waikiki can be tricky.
If you’re planning on staying local, then taxis, rideshares, and private drivers should be enough to get you by.
Oahu also has a bus system that runs through the island, including to the North Shore and Windward Coast.
And if you want to see more of the coast, then a boat charter is a great way to visit reef-filled coves, go deep-sea fishing, or check out different coastlines.
Your Concierge can help with rental cars, private drivers, boat charters, and more.

Best Time to Visit Oahu?

Peak season in Oahu is from mid-December to early January and again from June to August. This coincides with the usual vacation time for families. The weather is great, and there are surf competitions in the winter. If you want to visit at this time, book early.
Shoulder season is from mid-April to early June and from September to mid-December. The weather is great at this time, but there are fewer tourists. The surf is also calmer, so it’s a good time for swimming and snorkeling. For many, this is the best time to go.
Off season is from January to March (excluding New Year’s week). There’s more rain and the occasional cool breeze at this time. That said, there’s also great whale watching and big-wave surf in the north. This is a great time to find deals on Oahu luxury villas.

Is Oahu Safe?

Yes, Oahu is considered very safe. Violent crime is rare, and you can walk around most areas safely at night. Most of our Oahu luxury villas are also gated.
That said, the ocean can be unpredictable. Respect warning signs, and be advised that the North Shore surf in the winter can be big. Swim in designated areas only.

Best Things to do in Oahu?

Beach hop on the Windward Coast: Explore the white sands and turquoise water at Lanikai, Waimānalo, and Kailua Beach.
Visit Iolani Palace: Located in Downtown Honolulu, it’s the only royal palace in the US. Pair it with a walk through the historic Capitol District and Chinatown.
Hike Diamond Head Crater: This iconic, short hike offers sweeping views of Waikiki and the south shore. Try to go early to beat the heat.

How’s the Food in Oahu?

Oahu is the culinary heart of Hawaii, with a rich food scene featuring everything from beachside food trucks to high-end tasting menus.
There’s a big farm-to-table dining scene and a big emphasis on fresh seafood. Top local dishes include poke, plate lunch, spam musubi, and loco moco. In terms of seafood, be on the lookout for Ahi, ono, and opakapaka.’
And to drink, be sure to try some mai tais, lilikoi margaritas, kona coffee, or any of Oahu’s craft beers.
Your Concierge can also arrange private chef service and villa pre-stocking on most of our Oahu luxury villas.

How’s the Weather in Oahu?

Spring is warm and mild with gradually decreasing rain. Daytime highs range from 79–84°F (26–29°C) and nighttime lows from 65–70°F (18–21°C). Rainfall drops throughout the season, averaging about 1.5–2.5 inches (38–64 mm) per month. By May, skies are mostly clear and dry.
Summer is hot and dry with long, sunny days. Average daytime temperatures are 85–89°F (29–32°C), with lows between 71–75°F (22–24°C). Rain is minimal, typically 0.5–1.25 inches (13–32 mm) per month. Humidity is moderate, and trade winds help keep the air moving.
Fall stays warm, with a gradual increase in rain later in the season. Highs range from 84–88°F (29–31°C) and lows from 70–74°F (21–23°C). Rainfall averages 1.5–3 inches (38–76 mm) monthly, with November marking the shift into the wetter season.
Winter is the coolest and wettest time of year, though still pleasant by most standards. Daytime temperatures reach 78–82°F (25–28°C), with nighttime lows of 65–70°F (18–21°C). Rainfall is higher, typically 2–4 inches (50–100 mm) per month, especially on the east-facing (windward) coast.

Book an Oahu Luxury Villa with Rental Escapes

If you’re planning a getaway to this beautiful part of Hawaii, Rental Escapes can turn your Oahu villa rental into a true luxury experience.

Our portfolio includes the finest Oahu luxury villas, including beachfront villas, family villas, and more.

Your Rental Escapes Reservations Expert will help you find the perfect villa for your group, while your dedicated Concierge will customize your trip to ensure an unforgettable Oahu villa experience.

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