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Hawaii Getaways: Oahu, Big Island, and Beyond

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When it comes to vacation destinations, Hawaii offers plenty of options.

Composed of eight main islands, resplendent like green jewels in the middle of the Pacific Ocean’s sapphire waters, Hawaii is steeped in culture, history and beauty, with each island unique in its topography, history, attractions, and personality.

Thus, Hawaii is, and always will be, a destination people will want to return to again and again.  Luxury villas & exclusive rental residences also abound in Hawaii, which helps to explain the 10 million visitors the islands get each year.

Hawaii’s main islands are so distinctive, they have been given their own nicknames:

  1. Hawaii is the Big Island
  2. Kahoolawe is the Target Isle (not open to the public) 
  3. Kauai is the Garden Isle
  4. Lanai is the Pineapple Isle
  5. Maui is the Valley Isle
  6. Molokai is the Friendly Isle
  7. Niihau is the Forbidden Isle (not open to the public) 
  8. Oahu is the Gathering Place

While most can be explored, two islands have restricted access: Kahoolawe, which was once used by the US military during World War II, and Niihau, the Forbidden Isle, which has been privately owned by the Robinson family since 1864.

But there are many other islands you can check out with fabulous selections of oceanfront vacation rentals, cottages, and other luxury accommodations. Give in to what could possibly be once-in-a-lifetime experiences such as helicopter cruises or indulge in the exquisite offerings of upscale restaurants. You’ll never run out of choices on islands like Oahu, Big Island and Maui.

Luxury rentals on these and many other islands come with everything guests need to make the most of their Hawaii getaway. There are accommodations to suit personal preferences, a mix of restaurants that offer everything from local cuisine to Michelin-star concoctions, state-of-the-art outdoor sports facilities and gyms, and spas and wellness centers that offer the best in relaxation and pampering.

If you want to visit Hawaii, here are some things to consider.



Given the abundance of accommodations in Hawaii, it is important that you choose the right destination when planning a luxury Hawaii vacation.

At present, tourists have several options when it comes to accommodations, such as luxury resorts, private villas, and exclusive rentals, with each one having its own pros and cons.

Private villas on Oahu, the Big Island, and more

Luxury villas are another popular option for Hawaii’s visitors, especially those who prefer to travel in groups of up to 10 people. This is because unlike hotels, which rent out rooms individually, villas are booked in their entirety, which allows costs to be shared among guests.

This also means that guests have exclusive use of the property’s facilities such as gyms and pools without having to share them with strangers or having to wait their turn. In addition, guests also have the freedom to create their own itineraries, allowing them to fully personalize their vacation.

ON THE BIG ISLAND.Luxury villas in Hawaii include  Puako Paradise. Located on the sunny Kohala Coast, Puako Paradise has ​​over 4,000 square feet of living space composed of three luxurious master suites and a detached apartment, which means it can accommodate up to 10 people comfortably. Rented as a complete home, the villa boasts several essential features, such as private entryways, soaking tubs, covered outdoor showers for each of the suites, access to incredible ocean views, and a solar-heated pool and spa.

ON OAHU.One other notable luxury villa is Orchid House. Offering magical views of the Mokulua Islands from every room, this 3-bedroom, 4-bath custom home comes with top-shelf features such as solid hardwood floors, leathered granite countertops, slate stone flooring, a gourmet kitchen with modern appliances, skylights, and air-conditioned rooms. In addition, this single-level property also has a huge tree-shaded lanai, as well as a large, heated tropical pool featuring a waterfall, a lovely sun deck, and a cabana.

ON MAUI. Pililani is an exclusive villa that has 5 bedrooms and enough space to host a maximum of 10 guests. Taking architectural cues from Thailand, this luxury villa is just brimming with top-notch features and amenities, such as a 40-foot pool, a hot tub and sauna, a pool cabana equipped with a fridge and sink, patio tables and chairs, sun loungers, a custom outdoor shower, and even a full-size tennis court. Another property you can check out is  Pinnacle, one of the most stunning luxury villas in the area. Boasting 3,100 square feet of interior space, Pinnacle has four spacious bedrooms, with each one having its own ensuite bath. Moreover, the hilltop property has a spacious lanai and infinity pool, which allows guests to soak in the beauty of the island from sunrise to sunset.

Exclusive rentals on Oahu, the Big Island, and Maui

For visitors and holiday-goers looking to experience an intimate luxury Hawaii vacation, the archipelago’s exclusive rentals are an excellent choice.

Like luxury villas, these properties offer the utmost privacy and security, with the smaller square footage perfectly tailored for their target market, which is mostly couples and small groups of friends.

These rentals typically consist of compact luxury homes, condos, and cottage-style properties, which, despite their size, don’t skimp on top-tier amenities.

ON OAHU.One such exclusive rental is Naupaka Hale, an idyllic Hawaiian-style vacation beachfront home. A 3-bedroom property, Naupaka Hale offers breathtaking views of Lanikai Beach, the Mokulua Islands, and the area’s majestic mountains. Moreover, the property also has a large saltwater swimming pool in a private inner courtyard.

ON THE BIG ISLAND.Another property that visitors can check out is Hale Ohana. This 2,200-square-foot home has 4 bedrooms and 4 bathrooms. There’s a private dipping pool and a 1,000-square-foot covered lanai with lounge chairs, a dining table, a service area with a sink, and incredible views of the ocean.

ON MAUI.Located on the beautiful North Shore of Maui, Sugar Cove is a group of 18 townhomes sharing a landscaped 4-acre beachfront. Designed as a private retreat and a unique tropical vacation home, this particular townhome has 3 bedrooms, each with a private ensuite bathroom. Located just a mile down the beach from Paia town, or a few miles in the opposite direction to Kahului, this rental provides travelers peace and serenity throughout their stay. In terms of amenities, this property has a swimming pool, a tennis court, and launch access for activities such as windsurfing, kiting, paddle boarding, and boogie boarding.

Browse vacation rentals onOahu, theBig Island, andMaui



While Hawaii is predominantly known for its beaches and mountain trails, this gorgeous archipelago is also known for its slate of luxury destinations and attractions.

Eat well

No luxury Hawaii vacation is complete without sampling the best culinary delights – both high-end and casual – that the islands have to offer.

ON OAHU. Senia is considered to be among Oahu’s most refined dining destinations. Located in Honolulu and helmed by Anthony Rush, Senia’s menu features regional American favorites with a more modern twist. The braised beef cheeks, duck three ways, and triple-smoked salmon are must-tries. Another Oahu favorite that visitors should check out is Fête Hawaii. Led by James Beard award winner, Chef Robynne Maii, Fête Hawaii’s menu features unique dishes with French, Italian, Korean, and island influences. Their bestsellers include carbonara with Portuguese sausage, and rose veal schnitzel sauced with Hawaiian liliko‘i, along with specials that focus on the freshest Hawaiian seafood and produce.

ON THE BIG ISLAND. Here, holiday-goers looking to indulge in casual yet high-quality gastronomic delights can drop by Canoe House. The oceanfront restaurant serving Japanese-inspired dishes has become a beloved institution since it first opened its doors in 1989, delighting generations of diners. Today, executive chef Mark Libunao has reimagined the menu of this iconic dining destination while continuing its legacy. Open for dinner, the Canoe House encourages diners to share an array of small delectable dishes for a full flavorsome experience. View their men here

ON MAUI.If you ever find yourself in Maui, don’t forget to pencil in NUKA. Located in a small town on Maui’s North Shore, the 50-seat izakaya and sushi bar serves a selection of top-quality rolls and sashimi made under the supervision of Sushi Chef Hiro Takanashi. For a more casual dining experience, visit Nalu’s South Shore Grill. Open for breakfast, lunch, and dinner – plus happy hour – Nalu’s South Shore Grill serves classic All-American dishes with a Hawaiian twist, such as island-style ribs, crab cakes, and chicken and waffles.

Go on a wellness retreat

You can’t say you’ve been on a luxury Hawaii vacation if you haven’t given any of the archipelago’s selection of spas and wellness centers a try.

ON THE BIG ISLAND. Pay a visit to Hale Ho‘ōla Ma‘i Me Kapule, whose name roughly translates to the “house of faithful healing.” Located near the Kilauea summit, Hale Ho‘ōla Ma‘i Me Kapule is especially beloved for its spiritual approach to wellness, with spa packages designed to make visitors feel pampered, refreshed, and rejuvenated.

Another Big Island spa that visitors can visit is Kohala Spa in Waikoloa, a favorite among locals and tourists. The spa offers full body and area-focused treatments with unique features like a lava rock whirlpool and wet and dry spa treatment facilities, which can help bring relaxation and healing to guests. 

ON OAHU.Visitors in need of pampering will do well to check out  Moana Lani Spa. This facility is known for its impressive services, such as deep tissue massages and facial treatments. 

ON MAUI.Maui also has no shortage of top-quality spas and wellness centers, one of which is Ho’omana Spa Maui. An award-winning day spa, Ho’omana Spa Maui offers services such as sea clay purifying baths, sugar scrubs, and body masks, which they then finish off with traditional lomi lomi massages. In addition, Ho’omana Spa Maui also sells organic wellness products such as mists, body polishes, body butter, and bath salts – all of which are made in-house and only in small, limited batches. 


Deciding on where to have your luxury Hawaii vacation is not an overnight thing, given the number of luxury destinations that can be found all over Hawaii’s main islands which can make it difficult to decide on a place to stay. You will also have to carefully consider several things to make sure your accommodations fit the itinerary you’ve planned out to avoid logistical problems or small inconveniences during your trip.

To decide on the place you want to stay for your getaway, consider the following:

  • Location matters: Finding the ideal setting 

    It goes without saying that the location of your luxury villa or exclusive rental is of paramount importance. The location of your accommodations can make or break your vacation, after all. Before booking a luxury rental, make it a point to identify the places you want to visit and the activities you want to experience, as this can help you shortlist the places that will allow you to do all of those things.

    For instance, a vacation rental close to the city center is perfect for those who prefer being close to the best restaurants, theaters, and shopping centers. For seekers of peace and quiet, a more secluded retreat is in order. You’ll also have to factor in the distance to major highways and airports if you’re keen on convenience, especially if you’re traveling with kids, older adults, and people with special needs.

  • Luxury amenities: Discovering must-have features

    Another important thing that you have to consider when choosing a luxury villa or rental is the range of amenities they offer. The point, after all, of a vacation is getting the chance to spoil yourself with creature comforts and the comfy feel of being your home away from home.

    For that, you might want your luxury rental to have a plush resort feel, with a full complement of the softest towels and linens and a climate-controlled environment. You might also look for a full and functioning kitchen to enjoy the option of whipping up a quick snack or meal as your mood dictates. Because you’ll be on the beach a lot, or traveling with kids, a washer/dryer is a perk that comes in handy. Unless you truly want to disconnect, look for a luxury rental with a strong internet connection. To ensure a truly customized experience, check out the staggering array of vacation rental options and the amenities they offer on this link.

Browse vacation rentals onOahutheBig Island, andMaui


If you’re looking forward to a luxury Hawaii vacation, make sure to give Hawaiian Villa Rentals a call.

Part of Trinity Properties Hawaii, Hawaiian Villa Rentals provides a one-stop solution for visitors seeking perfect accommodations for their island getaway. Trinity Properties Hawaii has been in the industry for over 35 years, providing guests with long and short-term rentals that fit both budget and lifestyle.

One of the most valued real estate professionals in the state, the Hawaiian Villa Rentals team takes great pride in their ability to provide top-caliber, white-glove service to all of their clients. This includes talking to clients directly – no automated reply systems here! – and giving them the information that they need to find the perfect beachfront property that suits their needs.

Ready to make your luxury Hawaii vacation a reality? Give Hawaiian Villa Rentals a call today at 808.247.7521. You can also send a message here to get started.

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