Seasonal Rentals in Oahu | Oahu Condominium Rentals | Ola Properties

With ideal weather year-round, any season is pleasant for a getaway to the Hawaiian Islands. Activities such as swimming, surfing, stand-up paddleboarding, boating, hiking, and fishing can be enjoyed no matter which month you’re planning your stay at our Oahu condominium rentals . And of course, if you’re hoping to stake your claim on the most ideal stretch of pristine white sand, you will find it whether it’s winter, spring, summer, or fall.

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A Tropical Winter on Oahu

The season you choose for your retreat to Oahu may depend on what you’re hoping to do during your stay. For those with sights set on the whale watching aboard one of the many boat excursions available, the winter months are most ideal. From mid-December to mid-April, humpback whales migrate from frigid Alaskan waters to the warmth of Hawaii’s waters, where winter remains balmy. When you book a stay in one of our Ko Olina seasonal rentals, you can enjoy easy access to boat excursions that will get you out on the water viewing these magnificent creatures from a closer vantage point. Ko Olina Ocean Adventures and Ocean Joy Cruises Hawaii are both based out of the Ko Olina Marina, offering proximity and convenience for some of the island’s most exciting water activities. In addition to whale watching, ocean adventures such as snorkeling among tropical fish and dolphins, shark dives, sunset sails, dinner cruises, and more are all available from the Ko Olina Marina. Though whales can only be viewed during winter and early spring, any season is great for any of the other boating activities!

Winter also brings large surf to the island’s north shore, where world-renowned surfers flock to the island to catch record-breaking waves. While anyone unfamiliar with large wave surfing in this area will want to save their surf session for another time and place, it is still fascinating to head to some of the famed North Shore beaches to watch local surfers take on the waves like pros. Waimea Bay, Banzai Pipeline, and Sunset Beach are all renowned for their large winter waves, which can reach 25-30 feet, so be sure to choose a viewing spot that allows for plenty of room between you and the ocean. Chun’s Reef, Inside Hale’iwa, and Pua’ena Point are North Shore beaches that are better suited for beginners and intermediate surfers.

Low Season on Oahu

If your schedule is flexible, there are many perks to traveling to Oahu during seasons where peak tourism is low to take advantage of discounted airfare, activities, and accommodations. The busiest tourism windows tend to fall in line with school holidays, especially during Christmas break, spring break, and throughout the summer months. Traveling outside of those windows during the low season comes with its advantages. During low tourism seasons, you’ll find more beaches to yourself and less competition for booking activities to fill your Oahu vacation itinerary. And with Oahu’s consistently warm weather and perpetually sunny western coast, it is easy to enjoy a stay on the island during any season.

Features of Our Oahu Seasonal Vacation Rentals

Whether your getaway is for one week or one month, pamper yourself with seasonal rentals on Oahu that will bring all of your island’s dreams to fruition. Our seasonal rentals at Ko Olina and Makaha are located along Oahu’s sunny west coast, home to some of the island’s most stunning white-sand beaches and azure blue waters. The tranquil swimming lagoons fronting the Ko Olina seasonal rentals offer idyllic swimming and snorkeling conditions. Strung together by a 1.5-mile paved path lined with swaying palms, this is oceanfront living at its finest.

From romantic hideaways to luxurious 3-bedroom, 3-bathroom villas, there is something for every type of traveler at Ko Olina. Our Makaha seasonal rentals on Oahu are situated further north along the west coast, nestled between the dramatic Makaha Valley and the vast Pacific. Many of our Makaha seasonal rentals offer oceanfront living at a budget-friendly price. These vacation homes enjoy convenient access to the beautiful white sands of Makaha Beach Park, offering excellent swimming and snorkeling conditions. Browse our seasonal Oahu condominium rentals today to book your island getaway!

Contact Us for Our Rentals on Oahu

At Ola Properties, we specialize in luxurious Oahu condominium rentals in the oceanfront resort areas of Ko Olina Resort and Makaha. We have a large variety of beach villas, condos, and townhomes available for rent, many of which provide breathtaking ocean views or relaxing views of the golf green. Whether you’re planning a holiday trip, summer vacation, or long-term stay, we have the vacation rental you need. Our rentals are in perfect proximity for enjoying all of the best beaches and activities that west Oahu has to offer. Please contact us at (888) 737-4188 or (808) 726-2878, or via email at to book your vacation rental or to ask about our Oahu vacation rental services and to start planning your Hawaiian getaway! Check your calendar, pick a season, and come spend it with us on the sunny isle of Oahu!