CURATING
YOUR VILLAS

Oahu Villas & Luxury Vacation Rentals

North America  ·  USA  ·  Hawaii  ·  Oahu

66 Villas found
Paradise Cove Estate
from $ 7000 / nt
14 7 8
Banyan Hale
from $ 9300 / nt
12 7 9
Grand Kailua Beachside Estate
from $ 6000 / nt
14 7 8
Villa Diamond Head
from $ 3000 / nt
10 4 6
Plantation Paradise
from $ 4500 / nt
10 5 6
Royal Hawaiian Beach Estate
from $ 2999 / nt
20 9 7
Palm Tree Estate
from $ 1800 / nt
14 7 7
Kahala Mini Resort
from $ 3500 / nt
14 7 7
Hale Maluhia
from $ 2680 / nt
8 4 4
Lei Ahi
from $ 1500 / nt
8 4 5
Moana Lani
from $ 2675 / nt
10 5 6
Kailua Beachfront Vacation Rental
from $ 1100 / nt
14 5 6
Paradise Beach Estate
from $ 3296 / nt
8 4 5
Diamond Head Tiki Estate
from $ 1625 / nt
8 3 4
Walkers Lanikai Beach House
from $ 1400 / nt
14 5 4
Turtle Point Kailua
from $ 1400 / nt
9 4 4
Honu Heaven
from $ 1575 / nt
10 4 3
Portlock Oasis
from $ 1050 / nt
12 6 5

Oahu

Explore Luxury Vacation Rentals & Private Villas In Oahu

Discover and Enjoy Five Star Experiences In Oahu

When affluent travelers fantasize about luxury vacation experiences surrounded by the sybaritic pleasures of endless summer, Oahu always comes to mind. A one-stop-shop tropical destination, Hawaii’s third largest island offers an unrivaled taste of beachside living to visitors from across the globe. Whether planning your honeymoon or hosting a group retreat, you will find everything you need to enjoy a relaxing and luxurious holiday on Oahu, from white sand beaches and luxury villa rentals to upscale dining destinations and vibrant Hawaiian nightlife scenes. Oahu features a variety of beautiful and private vacation homes strategically located across the country, where you are looking to rent a luxury villa with an ocean view, in walking distance of Waikiki Beach, or nearby the island’s premiere s snorkeling sites and famous volcanic landmarks. Appointed with private pools, expansive beachside terraces, and many other contemporary amenities, affluent travelers enjoy a high standard of living when residing in Oahu’s luxury villa rentals.

Oahu is known as “The Gathering Place,” and for good reason. This Hawaii vacation destination is home to Honolulu, which comprises two-thirds of its population. For travelers to Hawaii pursuing the traditional luxury vacation experience, the capital city of Honolulu is a popular destination for renting private vacation homes or residing in luxury villa rentals. Hawaii’s bustling epicenter offers unrivaled cultural daytime activities, nature-based adventures, and upscale shopping establishments across its sprawling landscape. A walk around downtown Honolulu reveals a taste of Hawaii’s foremost business district, with a collection of high rise buildings comprising banks, offices, and commercial centers. Start your day off at Aloha Tower, a historic and monumental landmark that boasts stunning ocean views from its highest story. After a morning of shopping or grabbing a delectable Hawaiian treat at Aloha Tower’s dining marketplace, head to Chinatown. Here Oahu travelers will enjoy a vibrant arts district filled with eclectic and tantalizing visuals, as well as extravagant Pan-Asian cuisine to please any palette. Affluent travelers who choose to stay in Honolulu’s luxury villa rentals will find it conveniently located nearby Chinatown- a premiere Oahu nightlife hub. Here, all-night clubs and underground bars please tourists seeking the utmost extravagance past the twilight hours. And if Oahu nightlife isn’t on your agenda, a trip to Honolulu offers many other ways to indulge in a luxury vacation experience. For daytime activities focused on shopping, a trip to Ala Moana is a must; as Hawaii’s largest open-air shopping center, well-off travelers can spend hours perusing its offerings before returning to their private vacation homes for well-deserved downtime.

Honolulu’s southern shorelines feature Waikiki - one of Oahu’s most popular vacation destinations for many affluent travelers seeking a paradise retreat. With a famous stretch of gold sand beaches melting into turquoise waters, Waikiki features a plethora of upscale hotels and extravagant resorts for well-off visitors of a traditional beach holiday. But for a quieter take on this premiere Hawaii vacation destination, many travelers choose Waikiki’s luxury villa rentals for a week of ocean side living. Waikiki once attracted nineteenth century island royalty to its paradisiacal beach and sea atmosphere, and this affinity for high-end luxury remains alive and well across its shorelines. If sun tanning and snorkeling aren’t all you seek for a luxury Hawaii holiday, multiple other daytime activities sit in close proximity to Waikiki’s private vacation homes. Vibrant outdoor performances, outrigger canoe races, and hula dancing shows are popular daytime activities for those luxury travelers seeking an enlivened beach retreat. And when the sun goes down, open-air bars and rooftop lounges in Waikiki extend your opportunities to experience the Oahu nightlife.

To witness clear vistas of blue sky and sea, luxury travelers head straight to Makapu’u Point Lighthouse Trail, located in Oahu’s majestic Makapu’u Region. Visit Ko’oalau Mountain to marvel at expansive views from the Nu’uanu Pali Lookout, or tackle the imposing Diamond Head Crater, where the hiking trail ends in a Pacific Ocean vista so beautiful it is well worth the climb. Luxury travelers who seek premiere Oahu snorkeling sites will enjoy the luxury villa rentals nearby Hanauma Bay, where green sea turtles and magnificent coral reefs converge with four hundred species of fish. Meanwhile, surfers seeking incredible waves opt for private vacation homes on Oahu’s coveted North Shore – a world-famous surfing mecca. This renowned Hawaii vacation destination features massive waves for avid surfers looking for exhilarating adventure, in addition to numerous surfing schools for beginners who seek smaller thrills. Every December, the North Shore’s beaches come to life with a series of competitions, considered to be the Triple Crown of Surfing for both men and women’s professional surfing.

And if you grow tired of riding world-famous surf breaks, exploring snorkeling sites, or relaxing beachside by Hawaii’s luxury villa rentals, the island presents a world of historic daytime activities that appeal to affluent travelers exploring Hawaii’s breadth of history. Just some staple landmarks for a historic Oahu vacation experience include Pearl Harbor, the USS Arizona Memorial, the National Memorial Cemetery of the Pacific, and the scenic Valley of the Temples Memorial Park.

Make your holiday to Oahu, Hawaii, even more memorable by staying in one of Villaway’s luxury villa rentals. We have an excellent selection of Oahu private vacation homes prepared for your arrival, the ideal launch pads for travelers ready to launch a luxury vacation experience in Oahu. Choose an Oahu villa rental today through Villaway and get ready for a dream holiday to Hawaii.