With Exotic Estates, guests can rent an inspected Oahu vacation rental from Honolulu, over to Kailua on the Windward Side, and up to the North Shore. 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 Kailua vacation rentals to Honolulu, to beachfront North Shore rentals, they all offer unique charms and are beautiful vacation retreats. Please note that there are strict rules on Oahu that require 30 consecutive day rentals in most cases unless the unit is located in a resort area.
Oahu's Many Faces - Cosmopolitan & Country
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.
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 Oahu's dense urban side, anchored by Honolulu, and its more country 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 density and the scale of its buildings. There is urban sprawl emanating from downtown Honolulu to the East and West. To the East, the tangle of streets and buildings continues and ultimately turns 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.
Understanding Oahu's 30-Day Minimum Vacation Rental Rules
Oahu has some of the most strictly enforced vacation rental regulations in Hawaii. Understanding how these rules work is key to planning the right stay so you can manage expectations.
With these regulations in place, choosing the right property and the right location becomes more important than ever. Our team has lived on Oahu and toured homes and areas. We know the Island and the inventory well. We were founded in Hawaii and have been creating fabulous experiences for visitors since 2006.
With Exotic Estates, guests can explore a curated collection of professionally inspected vacation homes across Oahu, from Honolulu to Kailua and up to the North Shore. You are not on your own with Exotic Estates, unlike global rental platforms.
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.
Kahala is another neighborhood that is popular with regular visitors, located on the other side of Diamond Head. Exotic Estates has several oceanfront vacation homes for rent in and around Kahala. One is called Kahala Beachfront Aloha Villa, aand it's a family-friendly home with privacy, stunning ocean views, and plenty of space to spread out!
Staying in Kailua and Windward Oahu
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.
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 Kailua can easily join tours that will take them out to the shallow sandbars for swimming. A day out on the Bay is magical and guarantees 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 from November to April. During this time, the North Shore is a hive of surf activity, and it’s 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 shore, making it easy for visitors to enjoy the show from the comfort of the beach or a vacation home!
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!
