Oahu

Oahu welcomes cultural diversity not just in spirit, but in its neighborhoods. Each area of the island offers its own blend of scenery, lifestyle and pace—whether you’re drawn to luxury condos near nightlife or a secluded beach villa with direct access to the ocean.

Below, discover ten of Oahu’s most beloved destinations and find the perfect location for your next luxury vacation rental.

Ala Moana

Ala Moana is a vibrant coastal district where city life meets beachside leisure. It’s home to the world’s largest open-air shopping center and offers easy access to jogging trails, scenic parks and oceanfront views.

Many vacation home rentals in Ala Moana combine modern comfort with beach access and proximity to cultural spots—making this area a favorite among those seeking both relaxation and activity on the island of Oahu.

Diamond Head

Often called Hawaii’s Gold Coast, Diamond Head is one of the island’s most prestigious neighborhoods. With upscale condos and luxury vacation rentals lining the shoreline, it offers breathtaking views of the Pacific and access to the iconic crater trail.

Nearby parks and event venues like Kapiolani Park and Waikiki Shell enhance the area’s appeal. Travelers staying in this refined neighborhood enjoy a blend of nature and sophistication—hallmarks of many of Oahu’s most luxurious rentals.

Hawaii Kai

On Oahu’s southeast coast, Hawaii Kai blends quiet marina life with resort-style living. Originally developed by Henry J. Kaiser, this upscale suburb offers a peaceful retreat with scenic views and lush surroundings.

Just 12 miles from downtown Honolulu, Villa Leticia provides a tranquil escape close to city energy—ideal for guests seeking a luxury vacation rental away from the busyness but with easy access to urban highlights.

Kailua

Nestled along the island’s eastern shore beneath the Ko‘olau mountains, Kailua is a laid-back community celebrated for its natural beauty and outdoor spirit. Kayaking, kite surfing, and sunrise walks are part of everyday life here.

Set along the soft sands of Lanikai Beach, Villa Ariadne is one of the area’s most breathtaking beachfront vacation homes—perfect for families or couples craving space, serenity and direct beach access.

Kapahulu

Just outside Waikiki, Kapahulu offers a relaxed local vibe and an iconic culinary scene, from Leonard’s Bakery to the beloved Rainbow Drive-In. The neighborhood also features green spaces and easy access to the Honolulu Zoo and Ala Wai Golf Course.

Travelers can stay in cozy vacation homes or condos here, soaking in the charm of everyday life in Oahu while remaining close to beaches and urban energy.

Lanikai

Lanikai is one of Oahu’s most scenic oceanfront resort areas. Known for its calm waters and panoramic views of the Mokulua Islands, it’s ideal for swimming, kayaking and sunrise strolls.

The cluster of businesses in the middle of Lanikai includes restaurants in every variety and price range and small boutiques, only a 30-minute drive from Honolulu.

Manoa

Manoa Valley is a peaceful residential enclave rich in greenery and heritage. Boutique shops, family-run restaurants, and the Manoa Valley Theatre all add to its charm.

Vacation homes in Manoa provide a quiet escape surrounded by nature, placing guests near Manoa Falls and cultural sites that honor the traditions of the native Hawaiian community.

North Shore

The North Shore is a world-renowned surfer haven with legendary beaches stretching more than seven miles. Winter brings towering waves and global competitions like the Vans Triple Crown, while summer invites swimmers and snorkelers.

Luxury vacation rentals in this area—many right along the coast—deliver spectacular views of the ocean and a laid-back atmosphere, making the North Shore ideal for both thrill-seekers and relaxation lovers alike.

Waikiki

Waikiki is Oahu’s most iconic destination, famed for its golden beaches, vibrant nightlife, and walkable charm. The area blends high-rise energy with shoreline serenity, offering something for every type of traveler.

Stay at Banyan House, a stunning eight-bedroom villa just steps from the beach, perfect for groups seeking comfort, privacy and access to the best of Honolulu and Waikiki’s attractions.

Waimanalo

Waimanalo is a quiet community between the Ko‘olau mountain range and the sea, home to family farms, low-key eateries and some of the island’s most beautiful white-sand beaches.

For those seeking a slower pace and direct oceanfront access, Villa Tiarabelle offers a grand and serene stay—perfect for families traveling with children or anyone wishing to enjoy Oahu’s windward side in peace.

Oahu’s culinary scene is as rich and diverse as its landscapes, blending fresh island flavors with global influences. From elevated beachfront dining in Waikiki to hidden gems in the heart of Honolulu, these standout restaurants bring together atmosphere, innovation and ingredients rooted in Hawaii’s land and sea.

Whether you're staying in a luxury vacation home in West Oahu or a beach villa near Ko Olina, these dining destinations are never far away.

Azure

Located on the sands of Waikiki Beach, Azure is one of Oahu’s finest upscale restaurants. Known for pristine table settings and candlelit elegance, this oceanfront dining experience is perfect for guests enjoying a romantic Hawaii vacation.

Ideal for those staying in nearby Oahu villas or Waikiki vacation home rentals, Azure offers expertly prepared seafood and wine pairings in a setting that mirrors the luxury of the island itself—with unforgettable views of the ocean.

The Beach House

Blending Hawaiian hospitality with Pacific Rim cuisine, The Beach House is a local favorite known for its exceptional seafood dishes. Their world-class signature linguini with fresh fish and Kaua’i shrimp delights the senses with bold, buttery flavors.

Set near the coast, this restaurant is perfect for guests staying in oceanfront resort areas or beach villas with easy access to dining. It’s a great choice for families or couples seeking laid-back refinement in West Oahu.

Istanbul Hawaii

Get a taste of Turkish and Ottoman cuisine in Istanbul, Hawaii. Chef Ahu Hettema says the idea was to create the restaurant like a modern Turkish house.

The restaurant’s recipes have been in Chef Hettema’s family for generations. Try the Iskender Doner, Turkish spiced shaved lamb on Turkish saffron pilaf, Ho farm tomato reduction, Coban Salata, and tzatziki. Save room for the 40-layer homemade Baklava made with rare Hawaiian honey.

Located near luxury vacation rentals in Honolulu, Istanbul Hawaii provides a truly distinctive culinary experience for those looking to explore the cultural diversity that makes the island of Oahu so special.

La Mer

Consistently ranked among the best fine dining experiences in Hawaii, La Mer offers French-inspired haute cuisine in a beachfront setting.

Dinner starts with a flute of Champagne and an amuse bouche, two complimentary amenities that set the tone for a memorable and romantic repast. The menu offers an indulgent array of flavors, from seared duck foie gras and poached lobster with squid ink gnocchi to roasted lamb and duck breast.

For guests in luxury Oahu vacation rentals or Waikiki villas, La Mer is a quintessential destination—elevating your Hawaiian getaway with elegance, artistry and unparalleled ocean views.

La Vie

Perched on the eighth floor of The Ritz-Carlton Residences in Waikiki, La Vie serves modern French cuisine with an island sensibility. Dishes like truffled squab and sauce périgueux reflect the restaurant’s elevated style.

Whether celebrating or simply savoring a sunset meal, La Vie is a refined escape in the heart of Waikiki.

Merriman’s Honolulu

Known for pioneering Hawaii Regional Cuisine, Merriman’s blends a farm-to-table ethos with exceptional local ingredients. Its intimate setting and consistently fresh seafood have earned it accolades for over a decade.

Just minutes from many luxury Oahu vacation rentals and condos in Honolulu, Merriman’s is a must-visit for food lovers seeking a genuine taste of Hawaii in a relaxed, elegant environment.

Pai Honolulu

PAI offers flexible, seasonal dining that ranges from shareable bites to curated tasting menus. With its location across from the Aloha Tower, it draws locals and travelers alike for both casual lunches and celebratory dinners.

This spot is especially convenient for those staying in nearby vacation homes or villas in the heart of Honolulu, offering the perfect mix of urban flair and island flavor.

Roy’s Waikiki

Roy’s Waikiki has long been a cornerstone of the Hawaiian fusion movement. Located near Fort DeRussy, just a block from the beach, it serves flavorful dishes like Misoyaki Butterfish in an energetic and welcoming setting.

With easy access from condos, villas, and rentals in Waikiki, Roy’s is a go-to destination for guests seeking bold flavors and the island’s signature culinary style.

53 By the Sea

From its grand staircase to its minimalist dining room, 53 By the Sea impresses before the first bite. Floor-to-ceiling windows frame iconic views of the ocean and Diamond Head, setting the stage for contemporary American fare with Hawaiian touches. Contemporary American cuisine features fresh local seafood and a 32-ounce Tomahawk ribeye.

Located near some of Oahu’s most luxurious rentals, it’s ideal for special occasions, private dinners, or simply enjoying the artistry of food in a show-stopping setting on the coast.

The island of Oahu is the heart of Hawaii’s artistic and cultural expression. From royal history to contemporary exhibitions, these inspiring venues celebrate both the traditions of the native Hawaiian people and the global influences that shape the island today.

Hawaii State Art Museum

Located in downtown Honolulu, the Hawaii State Art Museum (HiSAM) showcases contemporary works by local artists in a bright, welcoming setting. Rotating exhibitions keep the experience fresh, while the sculpture garden offers a peaceful retreat filled with greenery and modern forms.

After viewing the art, enjoy a coffee at the on-site artisanal café or explore the museum shop for locally made keepsakes.

Honolulu Museum of Art

The Honolulu Museum of Art (HoMA) is the island’s premier art institution, with over 50,000 pieces spanning global traditions and centuries of artistic achievement. The museum opened in 1922 thanks in part to Anna Rice Cooke, the daughter of missionaries.

From Japanese woodblock prints to Impressionist painting, Hawaiian textiles and traditional pieces from Africa, Oceania and the Americas, the collection invites thoughtful exploration.

ʻIolani Palace

ʻIolani Palace is a rare treasure—the only royal residence on U.S. soil. Once home to Hawaii’s monarchs, this historic site offers a deeply moving look at the Kingdom of Hawaii’s final years and its lasting legacy.

The exclusive White Glove Tour adds an intimate layer, guiding visitors through the palace’s private archives. For those staying in luxury vacation homes near downtown Honolulu, a visit here provides a deeper understanding of the island’s royal roots and cultural identity.

Shangri La Museum of Islamic Art, Culture & Design

Tucked near Diamond Head, Shangri La is an oceanfront estate turned museum. It was once the private home of philanthropist Doris Duke. Her passion for Islamic art and architecture is reflected in every handcrafted tile, carved arch and vibrant textile.

This serene estate is just a short drive from many Oahu villas and luxury rentals near Waikiki and Diamond Head. A visit to Shangri La offers a striking contrast to island life—inviting guests into a world shaped by beauty, curiosity and global connection.

Oahu’s nightlife is as varied as its landscapes—ranging from relaxed lounges and oceanfront resort bars to energetic clubs in the heart of Honolulu. Whether you’re staying in one of the Hawaii villas near Ko Olina or a beachside rental in Waikiki, there’s always something after dark worth discovering.

From sunset hula beneath swaying palms to dancing the night away under strobe lights, these five venues reflect the island’s eclectic after-hours energy and charm.

House Without a Key

Set in the historic Halekulani Hotel, House Without a Key offers one of the most romantic settings in all of Oahu. A live Hawaiian steel guitar, traditional hula at sunset, and arguably the best mai tais in the world create an atmosphere steeped in nostalgia and island beauty.

Guests staying in oceanfront resort areas of Ko Olina or Honolulu villas will find this venue an ideal way to end the day, especially with late-night jazz continuing at Lewers Lounge until 2 a.m.

Mai Tai’s

For classic aloha vibes and panoramic views of Diamond Head, Mai Tai’s delivers a relaxing yet lively escape. Known for tropical drinks and local entertainment, this bar brings together visitors and locals for weekends filled with live bands and laughter.

O Bar

O Bar at the ‘Alohilani Resort is more than a lobby lounge—it’s a showcase of ambiance. The bar features craft beers, handcrafted cocktails, brown spirits, focused wines, and a farm-to-table menu featuring Makaweli Ranch beef; from the island of Kauai, and Waikiki.

With a 280,000 gallon, three-story saltwater Oceanarium, watching the aquarium sea life is a grandiose way to enjoy a signature beverage or two.

Rumfire

Located at the Sheraton Waikiki, Rumfire offers spectacular views of the ocean and Waikiki Beach. Signature cocktails, vintage rums and live DJ sets give this sleek venue an upscale energy that attracts a stylish crowd.

Ideal for guests staying in villas in Oahu with proximity to the beach, Rumfire is a great group outing option, especially during its vibrant happy hour events.

Zanzibar

Zanzibar blends exotic design with high-energy nightlife. Lavish decor, cutting-edge lighting, and a music mix from salsa to techno ensure something for every taste. Located in the heart of Waikiki, it offers comedy, dance nights and other lively happenings.

A favorite among travelers in oceanfront resort rentals or Waikiki condos available for rent, Zanzibar is a go-to for guests craving a cosmopolitan night on the town.

Whether it’s surf, art or flowers, Oahu knows how to celebrate. The island’s cultural calendar is packed year-round with events that honor heritage, highlight global creativity and bring the community together in joyful ways.

From the flower-laced elegance of Lei Day to high-octane surf competitions on North Shore beaches, these signature festivals reflect the essence of the Oahu destination.

Aloha Festivals

The largest Hawaiian cultural celebration in the U.S., Aloha Festivals brings music, dance, and aloha spirit to the forefront. What began in 1946 as Aloha Week is now a month-long statewide tribute to the traditions of the native Hawaiian people.

Whether staying near Kailua Beach or in one of the vacation rentals in the oceanfront neighborhoods of Honolulu, attending one of these vibrant events is a wonderful way to connect with local culture.

Hawaii Food and Wine Festival

Since its 2011 launch, HFWF has donated more than $3 million to community organizations supporting sustainability, culinary programs and agriculture.

This major culinary event draws over 100 international chefs, winemakers and mixologists for tastings, workshops and curated dinners. Spanning multiple islands, including Oahu, it celebrates Hawaii’s agricultural bounty and global flavor.

The Honolulu Festival

This annual gathering celebrates cultural harmony across the Pacific Rim. With performances from Japan, Tahiti, South Korea and Hawaii, it blends music, dance and art into one unforgettable weekend.

The event culminates in a colorful parade through central Honolulu—just minutes from many villas Oahu offers for rent in the heart of the city.

Honolulu Marathon

The Honolulu Marathon is the fourth largest in the U.S. This 26.2-mile event attracts runners from around the globe. The course winds past iconic sites, from downtown to Diamond Head, and along the island’s beautiful coast.

Whether you're a participant or cheering from the sidelines of your Oahu luxury villa near the best beaches and activities, the Honolulu Marathon is a dynamic highlight of winter in paradise.

The King Kamehameha Floral Parade

Held in honor of Hawaii’s unifier and first monarch, this parade showcases elaborate floats, marching bands, and costumed riders representing each island. The horseback procession through Honolulu is a colorful expression of Hawaiian history; dressed in 19th century riding gowns with colorful lei for riders and horses alike, the women represent princesses from Hawaii’s eight main islands.

Many guests staying in beach villas or oceanfront rentals in Honolulu plan their trips around this beautiful and symbolic annual event.

The Lei Day Celebration

Each May 1st, Hawaii celebrates Lei Day with pageantry, music and a stunning lei competition that showcases local floral artistry. Locals and visitors alike gather to honor this fragrant symbol of aloha.

From West Oahu to Waikiki, guests enjoy easy access to these charming cultural festivities, often held in open-air parks and community centers.

Pow!Wow! Hawaii

Held in Honolulu’s Kaka’ako district, Pow!Wow! transforms the city into a living canvas. Street artists from around the world collaborate on large-scale murals, while live music, workshops and pop-up markets create a citywide buzz.

Visitors staying near downtown Honolulu can explore the ever-changing art walk, making this one of the most interactive events the island has to offer.

Vans Triple Crown of Surfing

This king of all surfing competitions brings the world’s best wave riders to Oahu’s North Shore. On the right day, the swells of the North Shore winter are monstrous and captivating. These high-stakes waves truly separate the cream of the crop riders from the amateurs. With a total purse of more than $1 million, the Vans Triple Crown is set up as three separate surfing events held at various venues along the North Shore’s famed seven-mile miracle stretch: the Hawaiian Pro, Vans World Cup of Surfing, and Billabong Pipe Masters.

Adventure awaits on every shore of Oahu, whether you’re hiking volcanic ridges, exploring sacred valleys, or learning to surf. From cultural immersion to adrenaline-fueled fun, these activities show off the very best Oahu has to offer.

Best of all, many are located within a short drive from the island’s most luxurious vacation homes, oceanfront rentals, or villas in the resort areas of Ko Olina and Makaha.

Hiking to Diamond Head Crater

Diamond Head Trail is one of Oahu’s most iconic hikes. It’s a moderately short trek with major payoff—panoramic views over Waikiki, the Pacific and even parts of West Oahu.

Perfect for early risers staying in nearby vacation rentals, this hike offers a fresh perspective of the island and sets the tone for a day of exploration and beauty.

Kualoa Ranch

Known for its cinematic scenery, Kualoa Ranch offers horseback riding, ATV tours, and ziplining across lush valleys and ancient fishponds. It’s where films like Jurassic Park and Lost were brought to life.

This immersive experience is ideal for families staying in Hawaii villas near the windward coast or vacation homes looking for the best beaches and activities combined with cultural history.

Pearl Harbor Visit

A visit to Pearl Harbor is a powerful and educational experience. Explore the USS Arizona Memorial, the Battleship Missouri, and learn about the events that changed history.

Guests staying in villas in Oahu or in rentals in the oceanfront resort neighborhoods of Honolulu can easily make this meaningful excursion part of their itinerary.

Pearl Harbor Aviation Museum

Housed in two historic hangars, this museum brings WWII aviation history to life with rare aircraft, artifacts, and immersive exhibits. It’s a great stop for both history enthusiasts and curious travelers.

Vacationers based in the central or western areas of Oahu will find it an engaging activity just a short distance from many homes available for rent.

Polynesian Cultural Center

Located on Oahu’s North Shore, this center celebrates the culture, traditions, and food of the Pacific Islands. Hands-on exhibits, performances, and luaus bring this educational theme park to life.

Many guests staying in North Shore villas or homes near Kailua Beach find this one of the most enriching and family-friendly day trips on the island.

Private Surfing Lessons at Waikiki or North Shore

Whether it’s your first time on a board or you’re refining your skills, Oahu’s beaches offer ideal surf conditions for all levels. Professional instructors tailor the experience to your needs.

If you're staying near Kailua Beach or in oceanfront resort areas of Ko Olina, surf lessons are an iconic part of your perfect Oahu vacation—and boards are always provided.

Oahu’s luxury villas are designed to elevate your island experience, blending tropical beauty with elevated comfort. Whether you're staying in a beachfront estate along the North Shore or a secluded hideaway in the resort areas of Ko Olina, these vacation homes deliver thoughtful features tailored to relaxation, entertainment and privacy.

Here are some of the most sought-after amenities available in luxury vacation rentals across Oahu:

• Private pools with ocean or mountain views
• Direct beach access to white sand shores and calm lagoons
• Expansive lanais for outdoor dining and sunset lounging
• Gourmet kitchens with top-tier appliances and local design touches
• Spa-style bathrooms with soaking tubs, rain showers and natural materials
• Media rooms or home theaters for relaxed evenings in
• Fitness spaces or private yoga decks surrounded by nature
• Dedicated workspaces with high-speed internet for extended stays
• Concierge and housekeeping services for a seamless island stay
• Gated estates offering enhanced privacy and security

From the oceanfront resort areas of Ko Olina to the breezy North Shore, these villas offer more than just a place to stay—they offer space to unwind, reconnect and fully embrace the rhythm of island life.