Oahu Vacation Rentals & Villas

Oahu Vacation Rentals & Villas

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Oahu Vacation Homes & Villas

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 rental rules on Oahu that require 30 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 the 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 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. 

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!

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 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!

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!

Top rated rentals — Oahu

Get inspiration based on what other travelers search for
Royal Hawaiian Estate - Monthly Rental
Royal Hawaiian Estate - Monthly Rental
20· 9·Ocean View, Ocean Front, Pool, Hot Tub
Memory I will always cherish!
Standing by the ocean wall with my four year old son watching the waves roll in is a memory I will always cherish. Walking through the yard looking at the majesty of the volcanic ridge towering above the house was breathtaking. At night, doors open to the Lanai, the ocean lulls you to sleep or provides the perfect background for a romantic glass of wine by moonlight. The architectural design is the perfect balance of open spaces and private alcoves. While there are endless endeavors to be explored in Hawaii, the estate and beach provide everything that a family needs to have an authentic Hawaiian experience.
Lawrence N.
2017 Stay
Turtle Bay Villas 210
Turtle Bay Villas 210
8· 3·Ocean View
My family loved staying at the ocean villas and 210!
This was our third time at the ocean villas and first at 210. My family loved staying at the ocean villas and 210. It was a beautiful villa to stay at - plenty of space and great location (pool, beach and right next to turtle bay resort) - kids were able to take surf lessons, go horse back riding, snorkel & play tennis within turtle bay and zipline 10 min away. Food at the resort and plenty of food trucks close by at Kahuku are a treat. Great communication from the hosts.
Rajen S.
2021 Stay
Kahala Beachfront Aloha Villa - TVU#90/TVU-0376
Kahala Beachfront Aloha Villa - TVU#90/TVU-0376
14· 7·Ocean View, Ocean Front, Pool, Hot Tub
Love Kahala
We have been comin to Oahu for years and like Kahala area because it is so close to Waikiki and an easy drive up to Kailua for the beaches. This house was homey and right along the water, with a great pool. We would go out for the day and finish it off by the pool. We loved Waimanalo beach maybe next time we will stary there. Thanks to Bonnie and eveyone who made it such an easy process.
Mary C.
2019 Stay
Pacific White House
Pacific White House
10· 5·Mobility Friendly, Pool, Hot Tub
I Shall Return
Please make sure to name a suite after me! I shall return.
C. Sheen
2018 Stay

Oahu Destination Facts

Did you know...
Town & Country
Honolulu is a vibrant city home to 350,000, but Oahu also has a beautiful rural side called "Country" where old Hawaii still lives on.
Last Capital of the Kingdom of Hawaii
Honolulu is the only American city with a royal palace that was home to the last Hawaiian monarchs.
Warm Water Temps
Oahu's topaz blue waters range from 75F degrees in winter to 85F in summer.