Learn All About Oahu Before Your Next Stay | Ola Properties

Learn All About Oahu Before Your Next Stay

Looking for things to do on Oahu? Whether you're looking for relaxation or adventure, Oahu activities range from surfing to spas and everything in between. Be sure to experience authentic Hawaiian culture with our amazing restaurants on the island or get a local's perspective on sights and history with a guided tour.

A Winter Getaway to Oahu, Hawaii

As the winter months loom in the distance, many are already envisioning the impending cold weather and gray skies. Even when not residing in a cold-weather destination, the winter months can feel long without something to look forward to on the horizon. Whether you’re hoping to escape the snow for a while or are simply dreaming of summer days that slipped away too fast, a vacation to the Hawaiian Islands may be just what you need to add a bright spot to this winter’s calendar. Give yourself something to look forward to and slip away on a winter getaway to Oahu, Hawaii!

Best Winter Activities on Oahu, Hawaii

Because the Hawaiian Islands are blessed with year-round warm weather, the outdoor activities during winter are nearly endless. And with temperatures that drop slightly after sunset, the evenings are cool and comfortable. From wildlife watching to surfing epic waves, winter on Oahu promises endless fun! Be sure to add some of these top winter Oahu activities to your itinerary and enjoy the Oahu winter weather!

Whale Watching

It’s not just human travelers who make their way to Hawaii for the winter. This is also migrating season for humpback whales, who spend the winter months enjoying the warm waters surrounding the Hawaiian Islands. This makes winter a spectacular time for visitors to experience Hawaii’s exciting marine life. Whale spouts can often be seen from the shoreline for those who have a keen eye, but to truly appreciate the vastness of these mammals, travelers should consider a whale watching tour on Oahu. When it comes to whale watching outings, boat excursions can range from the fast, wild ride of a Zodiac to the leisurely cruising pace of a Catamaran. Both options will get you up close and personal with these stunning creatures, and you’re likely to spot dolphins and sea turtles along the way as well. Bring along your camera and capture amazing photos of Hawaii’s whales as well as scenic island views!

Beach Hopping

Of course, one of the best things about visiting Oahu in winter is that nearly every day is perfect for hitting the beach. The west side of Oahu tends to be the sunniest, and this coastline is graced with countless white sand beaches perfect for hitting the beach. The Ko Olina Lagoons are known for their picture-perfect calm waters framed by white sand crescent beaches. Enjoy a leisurely stroll along the beachfront path, lounge in the sand, or enjoy a refreshing swim, snorkel, or stand up paddle boarding excursion in the water. There are also nearby beaches perfect for surfing, whether you’re a complete beginner or you have some experience under your belt. Further up the western coast, the sands of Makaha Beach and seclusion of Yokohama Bay beckon, offering unforgettable beauty and spectacular Hawaiian sunsets. And of course, the famed beaches of Waikiki also await, with their bustling waterfront and abundant activities!

Celebrating the Winter Holidays in Hawaii

A getaway to Oahu over the winter holidays will mean even more potential activity options to add to the itinerary. Whether this is your first time away from home over the holidays or you’re used to a white Christmas, you’ll quickly realize that even on a tropical isle, a festive spirit is in the air. From palm trees strung with lights to shopping for gifts with a peppermint mocha in hand, you’re sure to enjoy the holiday season on Oahu. Be sure to add some of these Oahu holiday activities to your itinerary


Of all the Hawaiian Islands, Oahu tops the charts when it comes to the best shopping experience. From local pop-up markets that feature locally made goods to lavish shopping malls, the Oahu shopping experience will not disappoint. Ala Moana Shopping Center is the largest outdoor mall in the world, and it is located right here on Oahu. Even for reluctant shoppers, Ala Moana provides a pleasant experience with its open-air vibe and beautiful center stage that features entertainment such as Hawaiian music and hula. You’ll find everything from big-name brands to unique local finds at Ala Moana Center, with plenty of options for gift-giving.

Holiday Festivities

Christmas activities on Oahu include everything from watching Santa paddle his outrigger canoe onto the beach to catching a traditional rendition of The Nutcracker on stage. The Polynesian Cultural Center is also known for their Christmas activities, from a live nativity to a special snow day featuring real snow for the kids!

Winter Accommodations on Oahu

Whether you’re getting away for a week or planning to hide away for the entire winter, our Oahu in winter accommodations provide a great place to base your winter retreat. At Ola Properties, we offer upscale accommodations perfect for couples, families, and groups to enjoy an unforgettable winter in Hawaii. Contact our team with any questions you may have!

Best Times to Visit Oahu

With tropical weather year-round, you’ll enjoy a warm-weather getaway to Hawaii no matter what time of year you plan your vacation. Rather than marking the year by the colors of fall and snowfall of winter, there are some other considerations to keep in mind when planning a getaway to Hawaii. Be sure to consider these factors when determining the best times to visit Oahu!

Peak Tourist Seasons

Hawaii is on the bucket list for many travelers, and this can become apparent during peak tourist seasons. Oahu sees the most visitors between the months of December and March as travelers seek to escape the winter to a warm-weather getaway. With many families traveling over summer vacation, tourism picks up again from mid-June to the beginning of September. With a flexible schedule, there’s an advantage to planning your Hawaii getaway during off-peak times, when you’ll find fewer crowds and better deals on flights, accommodations, and car rentals. However, even during peak seasons there is still solace to be found, especially for those who are willing to travel off the beaten path!

Seasonal Advantages

The various festivities that pop up around the holidays make this an appealing time for many to head to the Islands. And between the months of December through March, you’ll also have the advantage of additional wildlife watching opportunities. This is when humpback whales can be spotted off the island’s coast, making it one of the best times to go to Honolulu!

While temperatures are a bit cooler in winter, making it a great time for hiking and other outdoor activities, it is still warm enough to enjoy days at the beach and time in the water. However, the warmest days will fall during summer months, perfect for spending long hours in the water trying out new activities such as surfing, boogie boarding, and snorkeling.

In Hawaii, the seasons dictate where you’ll find the largest swell and calmest waters. During the winter and spring, waves tend to be largest on the north and east shores and calmest on the south and west shores. In contrast, summer and fall bring larger waves to the south and west shores and calmer waters to the north and east. Keeping this in mind can help you plan which beaches will be best to hit during your stay!

Still in search of Oahu accommodations? Our Oahu vacation rentals are available during all the best times to visit Oahu! Contact us today!

Getting Around Oahu

Get away to the Island of Oahu for a Hawaiian vacation! Of all the Hawaiian Islands, Oahu offers the most comprehensive public transportation system. From exploring the shops of Honolulu to exploring the beaches of Waikiki and beyond, many destinations can be reached by public transport. Rental cars are also a popular option for visitors to Oahu due to the flexibility they provide. Here are some factors to consider when deciding the best Oahu transportation options for your trip to Hawaii!


Oahu’s city bus system, simply named TheBus, is an inexpensive way to get around Oahu. With the cost at just $2.75 per ride or $5.50 for a day pass, it’s easy to save on the transportation budget when you utilize the bus system. TheBus is best for shorter trips in and around Honolulu and Waikiki. It also helps to have a flexible schedule if opting to use TheBus. With traffic and frequent stops, this option tends to take a bit more time than the others.

Waikiki Trolley

When visiting popular tourist sites in Waikiki, the Waikiki Trolley can be a fun Oahu transportation option. Ticket prices vary depending on the line selected. Most of the trolley options are well-suited for a tour-like experience, taking visitors to popular Oahu sites such as Sea Life Park, Diamondhead, the Arts District, and Ala Moana Shopping Center.

Taxi & Rideshare

When you have a specific destination in mind and don’t want to deal with the extra time required to take the bus, a taxi or rideshare app such as Uber and Lyft are convenient options. While you can’t hail a taxi from the street as in many other big cities, taxi stands can be found at the airport as well as at many shopping malls and the business district. Rides can also be booked via your hotel concierge or by phone. Rideshare apps such as Uber and Lyft tend to be more economical, while taxis are generally the most expensive option for single trips around the island.

Car Rental

Renting a car provides the most flexibility for your trip to Oahu and is sensible if you plan to visit many sites around the island. However, car rentals can also be pricy and need to be booked in advance. For travelers who plan to spend most of their time relaxing around the hotel or resort with long sightseeing trips few and far between, this may be an unnecessary luxury.

Oahu Accommodations

Situated within a short drive from the Honolulu Airport, our Oahu vacation rentals are easy to reach and are located near beautiful white sand beaches. Browse our listings today after figuring out how you are getting around Oahu!

Our Top Oahu Travel Tips

When looking for a tropical travel destination within the US that offers world class beaches, cultural activities, historic sights, and activities, you can’t beat the Hawaiian Island of Oahu. Whether you’ll be spending your entire Hawaii vacation on Oahu, or you plan on doing some island hopping, these top Oahu travel tips will ensure you get all that’s desired out of your Hawaii vacation!

Travel During Off-Season

To get the best deals and avoid the crowds, consider planning your Hawaii vacation during the off-season. Hawaii’s peak travel season begins just before the winter holidays in December and extends through spring break in April. It picks up again from June to September with summer travel. If possible, head to Oahu and stay in one of our Hawaii winter rentals during the off-season from mid-September to mid-December or mid-April to mid-June in order to find emptier beaches and better deals.

Balance the Itinerary

It’s easy to go to extremes when traveling and either slip completely into vacation mode by lounging on the beach daily or packing the itinerary with memorable activities. In Hawaii, it’s best to balance the itinerary with a little bit of both. The Island of Oahu offers a wide range of activities, from historic and cultural sites to shopping and dining, golfing, hiking, land-based adventure activities, and water activities. While it’s tempting to try to squeeze it all in, you’ll miss the tranquil beauty that is characteristic of Hawaii without taking time to slow down and soak it all in. At the same time, lounging on the beach full-time means you’ll miss out on many of the things that make Oahu unique. On Oahu, it’s best to find the ideal balance between relaxation and adventuring to make the most of your stay!

Book Ahead

Especially if you’re traveling during peak tourist seasons, be sure to book things like a rental car far in advance. Rental cars and popular island activities tend to sell out quickly, leaving travelers scrambling for alternatives on arrival. For any of the activities that top your interest list, be sure to schedule those into the itinerary in advance!

Plan Your Beach Days

Set aside some time for lounging on Oahu’s world class beaches, keeping desired water activities in mind before selecting a beach. Oahu’s beaches all have their own atmosphere and personality, and while some may be great for surfing, others are best for lounging. Planning your beach days will help you know whether to bring along your favorite read or water toys such as surf and boogie boards!

If these top Oahu travel tips have you ready to book an island vacation, be sure to check out our Oahu vacation rentals here!

Planning Your Oahu Hawaii Vacation

If you’re fortunate enough to vacation on the tropical island of Oahu, Hawaii, it will serve you well to do some advance planning to make the most of your stay. Especially if you’ll be traveling during peak tourist seasons, which mostly fall during winter and summer months, advance planning will ensure you get your top choices when it comes to accommodations and activities. Consider some of these important factors when planning your Oahu Hawaii vacation!

When to Go

The weather in Hawaii is pleasant year-round, so there truly is no bad time to vacation in the islands. To avoid the crowds, consider traveling during the off-seasons between mid-April to mid-June or mid-September to mid-December. The dry season falls between April and October, so this is when you’re guaranteed the most sunshine. However, even during the months of rainy season there are normally long intervals of sunshine throughout the day.

Where to Stay

While Oahu is in large part known for the beaches and activities of Waikiki, it can serve travelers well to escape outside these busier areas to experience the tranquility and beauty that characterize island life. The western side of each island tends to have the driest, sunniest weather, making these areas ideal vacation destinations. West Oahu is dotted with spectacular white sand beaches and easy access to island activities. Here you’ll find everything from oceanfront condos to lavish private homes in gated palm tree-lined communities.

What to Do

There are beaches aplenty on Oahu, along with all the water activities that come with life along the coast, such as surfing, boogie boarding, stand up paddle boarding, swimming, and snorkeling, among others. In addition to days spent along the shoreline, Oahu’s interior is home to spectacular hiking trails, waterfalls, and adventure activities. Cultural and historic sights, shopping, and top-notch dining are all readily available on Oahu.


Of all the Hawaiian Islands, Oahu boasts the most efficient public transportation network, with buses that will transport you to most destinations across the island. However, if you plan on traveling to many island sites beyond Honolulu, travelers should continue renting a car for maximum convenience. Rental cars book up quickly, so this is an item that should be taken care of at the beginning stages of vacation planning.

Contact Us to Plan your Vacation to Oahu

Need more assistance in planning your dream vacation to Oahu? Contact us at Ola Properties, where our team is happy to help!

The History of Oahu

Long before the Islands of Hawaii became a top tourist destination, these lush oases were inhabited by Native Hawaiians. Although the exact date is unknown, these original inhabitants reached Hawaii from Polynesia by following the stars and birds via outrigger canoe. Each island became its own separate kingdom ruled by ali’i, or chiefs. While today the Islands are comprised of approximately 10 percent Native Hawaiians, the culture still permeates much of society. And with nearly 40% of the population being people with Asian origin, Hawaii has become a unique melting pot of cultures, forming a complex Oahu history.

Oahu was first spotted by western explorers in 1778 on Captain James Cook’s third Pacific expedition, and the first landing occurred in 1779 by Captain Clerke. Following this landing, an influx of whaling ships and missionaries had a drastic impact on the lives of Native Hawaiians. Hawaii continued to be reigned by monarchy until 1893, when Queen Liliuokalani was imprisoned in her palace, marking the end of the Hawaiian Monarchy and the beginning of annexation. ʻIolani Palace, the final royal residence of Hawaii’s rulers during its monarch days, can still be visited today in Honolulu, Oahu. It wasn’t until 1959 that Hawaii became the 50th state of the United States of America.

Sugar plantations became a major industry in the Hawaiian Islands in the 1800s, which brought in an influx of immigrants from China, Japan, Korea, the Philippines, and Puerto Rico to work on the plantations. The sugar industry played a large part in Hawaii’s economy until recent years, when the final plantation closed in 2016.

Though tourism began on the Big Island with the draw of the Kilauea Volcano, it quickly spread to Oahu soon after in the early 1900s with tourists arriving via steamships from California to the beaches of Waikiki. The arrival of jet liners in 1959 began the true tourism boom of Hawaii as we know it today.

Today, Oahu is well known for the historic site of Pearl Harbor, the location of the Japanese bombing that entered the United States into World War II. The beaches of Waikiki are still a top draw, both for the beauty of its beaches and the cosmopolitan vibe of the businesses and hotels along the oceanfront streets. Oahu’s North Shore is also famed for its big wave surfing, which brings in pro surfers worldwide during winter swells. With approximately 75% of the state’s population living on Oahu, this welcoming island has become dubbed The Gathering Place.

Offering a rich Oahu history, melting pot of cultures, and world class beaches, the Island of Oahu remains a special place to visit to this day. Check out our Hawaii vacation rentals in Oahu and come see for yourself!

Top Reasons to Visit Oahu

If a trip to Hawaii has been lingering on your travel bucket list, it may be time to make those dreams come true. The Hawaiian Island of Oahu is the most versatile of all the islands, making it a great destination option for families or groups whose members have a variety of interests. Whether you’re sneaking away on a getaway with a special someone or you’re trying to find a destination everyone from toddler to teen will enjoy, Oahu offers it all. These top reasons to visit Honolulu will leave you island dreaming and ready to pack your bags!

World-Class Beaches

The beaches of Waikiki are some of the most well-known in the world, offering beauty and a wealth of activities throughout the length of its shoreline. But Oahu’s coastline has even more to offer than the famed Waikiki stretch. From the big wave surfing beaches of Oahu’s North Shore to the quiet, picturesque coves of Ko Olina, it’s easy to immerse yourself in Oahu’s miles of world class beaches. Whether your idea of the perfect beach day includes lounging in the sun or trying out a new water sport, you’ll find plenty of postcard-perfect beaches to choose from on Oahu.

Shopping & Dining

While Oahu offers its share of natural beauty, you’ll also find many sites and activities that will keep everyone entertained when you’re ready for a break from the beach. Of all the Hawaiian Islands, Oahu offers the most extensive shopping and dining experiences. In fact, it is home to Ala Moana Center, the largest open-air shopping mall in the world. Among Oahu’s shops, you’ll find a broad mixture of everything from locally crafted goods to beachwear to high end fashion brands. And on the dining front, you’ll discover both hidden local eats and lavish oceanfront restaurants meant for celebrating a special evening out.

Adventure Activities

Though you can certainly opt to lounge away your days on a postcard-perfect beach, Oahu has much to offer beyond its shoreline. Adventure activities abound, from diving with sharks to seeing the sights from a doors-off helicopter tour. Hiking, exploring waterfalls, ziplining, surfing, snorkeling, and kayaking are just a few of the adventurous ways you can explore the island. Whether seeking a land-based or water-based adventure, Oahu is an outdoor playground!

Top Accommodations

Oahu is also home to a wide variety of accommodation options, from budget-friendly to luxurious. Browse these Oahu accommodations based on the island’s picturesque western coast and start envisioning your visit to Oahu! Contact us today!

Top Things you May Not Know about Honolulu and Oahu

While most visitors to Oahu have heard of famed locations such as Honolulu, Waikiki, and Pearl Harbor, many find there is much more to discover upon arrival to the island. Offering so much more than just these well-known locales, Oahu surprises visitors at every turn. With geographic features that range from waterfalls to mountain spires and a community rich with history and culture, an exciting dynamic awaits on Oahu. Before taking flight, delve a little deeper into your vacation destination by learning these top things you may not know about Honolulu and Oahu!

Site of Hawaii’s Final Reigning Monarchy

Before Hawaii was overtaken, it was ruled by a Native Hawaiian Monarchy. The final reigning monarchy resided in the Iolani Palace, which is located in what is today Honolulu, Oahu. This National Historic Landmark was built in 1882 and has been carefully restored. This is the only Royal Palace in the United States, making it a unique site to visit. Today, visitors can embark on either a guided tour or self-led audio tour, complete with special gallery exhibits.

A Destination with Over 125 Beaches

While it’s no secret that Oahu is a top beach destination (this is a well-known fact about Oahu), many visitors’ knowledge of beaches ends with the well-known stretches of Waikiki and the beaches along North Shore, which have made a name for themselves in the surfing circuit. However, this small island is actually home to over 125 beaches. So, while you may be tempted to spend your days lounging along a pristine stretch of sand, you may want to add some beach hopping to the itinerary to discover some of Oahu’s best beaches!

Home to Monster Surfing Waves

Hawaii is well known as the birth place of surfing. Specifically on the Island of Oahu, the North Shore is a top destination for surfers from around the world when it’s being hit with its large winter swells. Until recent years when larger waves have been surfed off Portugal’s coast, Oahu was home to the largest wave ever surfed – an 85-foot monster taken on by Ken Bradshaw. This 1998 feat took place at the surf location known as Outer Log Cabins. While you’ll want to keep your distance from any such sizeable swells, there are also plenty of surf spots on Oahu that are ideal for beginner and intermediate surfers, as well as many options for surf lessons on Oahu.

Still in search of your Oahu accommodations? Browse our listings at Ola Properties!