36 Villas in "Oahu"

Explore Oahu Villas

Renting an Oahu Villa with Exotic Estates

With Exotic Estates, guests can rent an inspected Oahu vacation home from Honolulu, over to Kailua on the Windward Side, and up to the North Shore. Exotic Estates is a boutique vacation rental agency that only lists homes that meet strict quality standards. Our Oahu vacation villas and estates have been selected for their location and quality. Some homes are true estates, offering opulent lodging in desirable locations, while others have a more family-friendly feel, but each will offer a high-quality vacation home rental experience that meets the tastes and needs of our travelers. From vacation homes in Honolulu and Kailua, to beachfront North Shore homes, they all offer unique charms and are beautiful vacation retreats. 

Oahu's Many Faces - Cosmopolitan & Wild

The Island of Oahu, known as “The Gathering Place,” offers visitors an unrivaled experience of island life with both town and country elements. Oahu is the third largest island in the main Hawaiian chain and it offers the most varied attractions, making it a truly unique vacation destination. During one well-planned day on Oahu, it is possible to watch professional surfers in action on some of the biggest waves in the world at famous North Shore beaches, enjoy a 5-star dinner with ocean views, and see a piano concerto with the Hawaii Symphony Orchestra in Honolulu. Amazing experiences await all visitors with historical expeditions to Iolani Palace, the only royal residence in the United States, the Bishop Museum, Pearl Harbor, and the Honolulu Academy of Arts.

Savor long, relaxing beach days enjoying the crystal-clear blue waters of Kailua Beach and Lanikai. Or, enjoy the cityscape and southern coastline from Waikiki Beach, after a day of shopping at Ala Moana Shopping Center. Visit luxurious spas or just enjoy the laid back vibes of Oahu with a Mai-Tai in hand poolside, from the comfort of your own private vacation home.

Opportunities and advantages are endless on this island, with only you to make a decision about where you want your vacation home to be, and how you’d like your dream vacation in Hawaii to unfold. Let Exotic Estates help you tailor a luxurious, dream vacation on Oahu.

Oahu Town & Country

When you think about Oahu as a destination, it's helpful to look at the island as being divided between town and country. There is even a surf brand that bears the name T&C. What this refers to is the Oahu's dense urban side, anchored by Honolulu, and its more wild side, which includes the Windward coast, the famed North Shore, and the western part of the island.

Honolulu has grown into a major city, with skyscrapers and a bustling business district. The city is startling at first sight for its denseness and scale of its buildings. There is urban sprawl emanating from the epicenter or downtown Honolulu to the East and West. To the East, the tangle of streets and buildings continue and ultimately turn into Waikiki, a city of high-rise hotels and condos ringing the sands of ever-popular Waikiki beach and bookmarked by the proud profile of Diamond Head crater. 

Renting a Vacation Home in Waikiki and Honolulu

There are many gorgeous vacation homes for rent in and around Honolulu in the most desirable areas. Our Waikiki homes are actually located in quiet neighborhoods located at the foot of Diamond Head crater. This area, once referred to as the Beverly Hills of Hawaii, is green and quiet, yet with easy access to Waikiki's restaurants, bars and shops. 

A perk of renting a vacation home in the Diamond Head area is that the stretch of beach located at the foot of Diamond Head crater are quiet and frequented by locals as much as visitors. With the green space of the great Kapiolani Park just across the street, the stretch of beach is known at the Gold Coast. Exotic Estates vacation homes are within walking distance of these beaches and offer access to the park for morning and evening runs.

Kahala is another neighborhood that is popular with regular visitors, located on the other side of Diamond Head. Exotic Estates has several oceanfront vacation home for rent in and around Kahala. One is called Kahala Views Luxury Villa, and it's a family-friendly home that offers privacy, stunning ocean views and lots of room people to spread out!

Honolulu Hillside Vacation Home

Another special Honolulu vacation home is the Manoa Canopy Villa, tucked away on a hillside in the green Manoa Valley, just behind Honolulu. This unique hillside home puts you in the midst of Honolulu's rainforest, surrounded by lush green foliage and the sounds of Hawaiian birds. Complete with an infinity-edge pool, screened in porch and outside BBQ and dining area, the home gives new meaning to the term glamping!

Staying in Kailua and Windward Oahu

Kailua is a gem of a town that sits on Oahu's Windward - or eastern - coast. This is the side of the island that faces the oncoming trade winds. The Windward coast is separated from Honolulu and the southern coast but the towering Koolau Mountains. This stunning range creates a towering wall of green, like something out of King Kong. Thanks to the Pali Highway, getting from one side of the island to another is just a short and unbelievably scenic ride over the Nuuani Pali. 

Kailua sits on the coast and it's biggest draw are its epic beaches. World-famous Kailua Beach Park and Lanikai Beach offer calm waters painted in remarkable shades of blue. You can rent a house in Kailua on the beach or on the hillside overlooking the coast and offering views of the outer islands, referred to locally as the Mokes.

Ultimately, Kailiua is popular with families looking for a quiet town to enjoy together time in a great Hawaiian villa and perfect beach days. The homes here range from charming, renovated plantation style properties to epic modern beachfront houses boasting private theaters and resort-like amenities. Guests find all the comforts of home in Kailua town, from supermarkets to salons, as well as Hawaiian-style eateries. 

North of Kailua is the town of Kaneohe, which sits on the striking waters of Kaneohe Bay. This stretch of coast oozes Polynesia, with its jagged green peaks and blue waters. Kaneohe Bay looks like a location from The Bounty or Blue Lagoon and visitors staying in Kailia can easily join tours that will take you out to the shallow sandbars for swimming. A day out on the Bay is magical and guarantee enviable photos for Facebook or Instagram!

Oahu North Shore Rentals

Many travelers have heard of the North Shore of Oahu, made famous for its world-class surfing. What many do not know, is that the high-surf is seasonal, showing up during the winter months, roughly between November and April. During this time, the North Shore is a hive of surf activity and its truly exciting to be a part of the scene and take in the amazing energy. What makes this big surf area so unique, is that all the action takes place roughly close to share making it easy for visitors to enjoy the show from the comfort of the beach or a vacation home!

Exotic Estates offers a couple luxury vacation homes on the North Shore of Oahu that check all the boxes - beachfront, privacy, luxurious amenities and location, location, location! Check out our North Shore Oahu Vacation Homes!

Oahu Vacation Guide

Please review our Oahu Guide for a handy overview of what to see, do and eat on the Hawaiian island of Oahu!

Exotic Estates is proud to be a Preferred Affiliate of Hawaiian Airlines, which offers award-winning nonstop service to Hawaii from 11 North American gateway cities.   

As a Preferred Affiliate, clients of Exotic Estates are able to save up to 5% on the cost of air travel to Hawaii from the US Mainland.   Read more about the program on our Hawaiian Airlines Preferred Affiliate page.