Tips on Finding Hawaii Vacation Deals
Save time and money by booking your rental car, hotel room, and airfare together and make planning your vacation easier.
How to Find the Cheapest Vacation Packages
Dreaming of a Hawaiian getaway that doesn’t break the bank? You’re not alone. The good news is that with a little savvy travel planning and timing, visiting paradise can be surprisingly affordable. Whether you’re keen on island-hopping or planning a longer stay on one island, here’s how to score the best vacation deals without sacrificing the magic of the Aloha spirit.
Traveling Smart: Understand Hawaii’s Seasons
Understanding Hawaii’s travel seasons is the key to unlocking savings. Peak travel times—summer (June through August) and winter (mid-December through March)—are the most popular meaning they’re higher priced. During these seasons, flights, hotels, and excursions can spike significantly.
But here’s your golden window: the shoulder seasons in spring (April to early June) and fall (September to mid-December). During these off-peak months:
- Prices for airfare and accommodations drop.
- Beaches and attractions are less crowded.
- The weather? Still dreamy, with warm temps and fewer showers.
Insider tip: Sign up for fare alerts through travel sites like Hopper or Google Flights. These tools track trends and let you know when prices dip.
Should You Book an All-Inclusive Package?
Planning a trip is, what we call in Hawaii slang “humbug.” It’s a bother, a nuisance—even stressful. But it doesn’t have to be. All-inclusive packages simplify things and often offer great value, bundling flights, hotels, and rental cars into one discounted price.
Some benefits of all-inclusive packages:
- Easier budgeting with one upfront cost
- Lower per-person cost than à la carte bookings
- Bonus perks like resort credits or free breakfasts
Pro tip: Search on trusted platforms like Expedia, Costco Travel, or Hawaii.com’s vacation deals to compare package options.
Best Areas to Stay on Each Island
Each island has its splurge-worthy resorts, but there are also affordable gems perfect for budget-conscious travelers. Here’s a breakdown of where to find great deals without sacrificing location or comfort:
- Oʻahu – Waikīkī: This iconic beach neighborhood offers a mix of high-end resorts and budget-friendly hotels, all within walking distance of shopping, dining, and world-famous Waikīkī Beach. Plus, public transportation makes it easy to get around without renting a car.
- Maui – Kāʻanapali: Known for its golden beaches and walkable beachfront resorts, Kāʻanapali combines luxury and convenience. Look for off-season hotel deals and vacation rentals with kitchenettes to save on dining.
- Kauaʻi – Poʻipū or Hanalei: Whether you want sunny shores or lush jungle vibes, Kauaʻi delivers. Poʻipū offers reliable sunshine and family-friendly condos, while Hanalei gives you access to the stunning North Shore without resort-level prices.
- Big Island – Kailua-Kona or Hilo: Kona’s sunny coast is home to affordable condos and seaside hotels, while Hilo offers a more laid-back, rain-forest atmosphere with easy access to waterfalls and volcano hikes.
The Top 3 Hotels and Resorts on Each Island
While scoring a great deal is important for travel planning and budgeting, it’s also important to know which hotels deliver an exceptional experience every time. These resorts continually top lists in hospitality, amenities, and charm based on customer reviews, industry accolades, location, and overall value for travelers. Whether you’re booking an all-inclusive package or building your trip à la carte, these properties will ensure your trip to Hawaii is one for the books.
Oahu
Hilton Hawaiian Village Waikīkī Beach Resort
Nestled on the widest stretch of Waikīkī Beach, this iconic resort offers five pools, a saltwater lagoon, nightly entertainment, and direct beach access—all just steps from world-class shopping and dining. Perfect for families, couples, and first-time visitors, it’s the ultimate home base for exploring Honolulu. With its blend of island luxury and endless activities, it’s no wonder this is one of Hawaiʻi’s most booked resorts. Book Now
The Ritz-Carlton Residences, Waikīkī Beach
This ultra-luxury resort blends high-end living with five-star service, offering spacious residential-style suites, gourmet dining, and two infinity pools overlooking the Pacific. Located just steps from Waikīkī’s best beaches and boutiques, it’s a sanctuary for travelers who crave sophistication and serenity that frequently tops the list of Honolulu’s most sought-after stays. Book Now
Halekulani Hotel
A timeless icon of Hawaiian hospitality, Halekulani offers refined oceanfront rooms, serene courtyards, and exceptional dining—including the legendary House Without a Key. Just moments from Waikīkī Beach yet worlds away in ambiance, it’s a favorite for discerning travelers seeking elegance, relaxation, and impeccable service. Book Now
Maui
Four Seasons Resort Maui at Wailea
Set along golden Wailea Beach, this world-renowned resort features three oceanview pools, award-winning restaurants, and spacious suites designed for ultimate comfort and privacy. With unmatched service, curated cultural experiences, and a prime location for sunsets and stargazing, it’s a dream destination for honeymooners, families, and luxury travelers alike. Book Now
Wailea Beach Resort – Marriott, Maui
Blending modern luxury with Hawaiian charm, this oceanfront resort boasts multiple infinity pools (including one with a waterslide), serene tropical gardens, and panoramic views of the Pacific. With its unbeatable location between Wailea and Ulua beaches, plus spacious rooms and cultural programming, it’s one of Maui’s most bookable stays for both families and couples. Book Now
Maui’s only all-suite and villa luxury resort, Fairmont Kea Lani offers oceanfront elegance with oversized lanais, tropical gardens, and three sparkling pools—including an adults-only retreat. Located on sun-kissed Polo Beach, it’s a top pick for travelers seeking a peaceful escape with the comforts of home and the indulgence of five-star service. Book Now
Kauai
Perched above Kauaʻi’s breathtaking North Shore, this eco-luxury retreat redefines wellness travel with nature-inspired design, organic dining, and immersive spa experiences. Surrounded by lush cliffs and cascading waterfalls, it’s the ultimate sanctuary for those seeking rejuvenation and island serenity. Book Now
Set on the golden sands of Poʻipū Beach, this welcoming resort features oceanfront dining, lush garden paths, and nightly sunset rituals that celebrate local culture. Whether you’re snorkeling steps from your room or sipping mai tais poolside, it offers the perfect mix of island adventure and laid-back luxury. Book Now
Grand Hyatt Kauai Resort & Spa
Nestled along the sunny shores of Poʻipū, this grand oceanfront resort blends Hawaiian elegance with lush gardens, saltwater lagoons, and a sprawling pool complex complete with waterfalls and a lazy river. With a world-class spa, cultural activities, and incredible dining, it’s a luxurious oasis for both adventure and serenity seekers. Book Now
Hawaiʻi Island (Big Island)
A timeless icon on the Kohala Coast, this mid-century modern gem sits on one of Hawaiʻi’s most beautiful white-sand beaches. With championship golf, curated art collections, and elegant oceanview rooms, it offers classic island luxury that keeps guests returning generation after generation. Book Now
Tucked along the serene Kohala Coast, Fairmont Orchid blends tropical luxury with Hawaiian tradition, offering oceanfront dining, a world-class spa, and a protected white-sand beach perfect for snorkeling. From sunset canoe paddles to lush garden paths, it’s a tranquil escape that invites you to unwind in style. Book Now
A hidden gem on Hawaiʻi Island’s lush Hāmākua Coast, every oceanfront room includes a private lanai, curated tastings, and unforgettable cliffside views. With just eight luxurious suites, a resort-style infinity pool, and a coastal trail that leads straight to the sea, this tropical retreat blends serenity, storytelling, and exclusivity. Book Now
Best Value Hotels and Resorts on Each Island
Dreaming of paradise doesn’t have to mean splurging on luxury resorts. Across Hawai‘i’s six main islands, there are hidden gems that offer comfort, charm, and unbeatable value. Whether you’re a budget-savvy traveler or simply want more aloha for your dollar, we’ve rounded up the best places to stay—from beachside inns to boutique hotels—that prove an unforgettable Hawaiian vacation doesn’t have to break the bank.
Oʻahu
VIVE Hotel Waikīkī
Chic, smart, and just minutes from the sand, VIVE Hotel offers a stylish boutique stay with modern rooms, complimentary breakfast, and warm aloha hospitality. It’s a favorite for savvy travelers who want comfort and convenience in the heart of Waikīkī. Book Now
Coconut Waikīkī Hotel
Bright, breezy, and full of personality, Coconut Waikīkī Hotel offers colorful island-inspired rooms, a heated pool, and complimentary breakfast—all just steps from the Ala Wai Canal and Waikīkī’s bustling shops and restaurants. A cheerful, budget-friendly base for exploring Honolulu. Book Now
White Sands Hotel
A retro-chic hideaway in the middle of Waikīkī, White Sands Hotel blends vintage Hawaiian vibes with modern flair—complete with a tropical courtyard, poolside bar, and swinging lounge chairs. It’s a nostalgic escape just minutes from the beach, perfect for laid-back travelers with a love for design and charm. Book Now
Maui
Maui Beach Hotel
Conveniently located in Kahului near the airport, Maui Beach Hotel is a practical and affordable home base for exploring the island and Maui’s central attractions. With spacious rooms, an outdoor pool, and proximity to shopping and dining, it’s a solid choice for travelers who want comfort and convenience without the resort price tag. Book Now
Set on 11 tropical acres along Kāʻanapali Beach, this laid-back resort offers spacious studios and suites with full kitchens, two pools, and a beachfront restaurant. It’s a peaceful haven with old-school Maui charm—perfect for families, couples, or anyone craving a slower pace just steps from the ocean. Book Now
Royal Lahaina Resort & Bungalows
Tucked along the golden sands of Kāʻanapali Beach, this classic Maui resort offers oceanview rooms, three pools, and charming beachside bungalows surrounded by swaying palms. With nightly lūʻau, on-site dining, and a relaxed island vibe, it’s a beloved favorite for travelers seeking both comfort and aloha. Book Now
Kauaʻi
Outrigger Kaanapali Beach Hotel
Often called “Hawaiʻi’s Most Hawaiian Hotel,” The Outrigger Kāʻanapali Beach Hotel blends cultural immersion with genuine aloha spirit—offering hula lessons, lei making, and storytelling in a relaxed beachfront setting. With its lush gardens, central Kāʻanapali location, and heartfelt hospitality, it’s a treasured favorite for those seeking an authentic Maui stay. Book Now
This laid-back, oceanfront boutique hotel in Kapaʻa offers sunrise views, complimentary bikes and yoga, and an inviting pool just steps from the sea. With retro-chic vibes and easy access to Kauaʻi’s east coast adventures, it’s a favorite for travelers seeking value, charm, and relaxation. Book Now
Bright, breezy, and right on the beach, this colorful Kapaʻa retreat features modern island-style rooms, two pools, and the popular Lava Lava Beach Club just steps from your door. It’s a laid-back, affordable base for exploring Kauaʻi’s lush east coast and soaking up the sunrise. Book Now
Hawaiʻi Island (Big Island)
Tucked away on 42 private acres near Hilo, The Inn at Kulaniapia Falls offers a peaceful retreat centered around its breathtaking namesake waterfall. This eco-friendly boutique inn features Asian-inspired rooms, farm-to-table breakfasts with unique experiences like bamboo cooking classes and waterfall rappelling nearby. Book Now
Castle Hilo Hawaiian Hotel
With sweeping views of Hilo Bay and majestic Mauna Kea, this full-service hotel offers spacious rooms, an oceanfront pool, and on-site dining—all just steps from the peaceful Liliʻuokalani Gardens. It’s a top choice for travelers seeking comfort, convenience, and classic Big Island charm. Book Now
Hilo Reeds Bay Hotel
An affordable oceanfront gem, Hilo Reeds Bay Hotel offers basic rooms with private lanais and views of the bay, just minutes from Hilo’s farmers markets, beaches, and downtown. It’s a quiet, convenient base for exploring the lush east side of Hawaiʻi Island. Book Now
Which Hawaii Island is Best for You?
Kauai’s picturesque Na Pali Coast.
Kauaʻi – The Garden Isle
For nature lovers and adventure seekers, Kauaʻi is a verdant escape filled with dramatic cliffs, lush rainforests, and hidden beaches. Hike through the Nā Pali Coast, kayak the Wailua River, or explore botanical gardens that feel like scenes from a dream. This island is perfect for those craving solitude, scenic beauty, and untamed wildness.
Sunrise over Na Mokulua islands from Lanikai Beach on Oahu.
Oahu – The Gathering Place
Where most people fly into, Oʻahu strikes a perfect balance between modern conveniences and island adventure. From surfing in Waikīkī to hiking Diamond Head or exploring historic Pearl Harbor, there’s something for everyone. It’s especially great for families, offering a wide array of kid-friendly (keiki) activities, shopping, dining, and nightlife—all with a backdrop of golden beaches and towering green peaks.
Waianapanapa State Park, Maui.
Maui – The Valley Isle
Maui is a romantic’s paradise, filled with luxury resorts, stunning beaches, and unforgettable experiences. Watch the sunrise from Haleakalā, drive the winding Road to Hāna, or snorkel with sea turtles at Molokini Crater. It’s ideal for couples, honeymooners, and travelers looking for equal parts relaxation and exploration. The vibe here is upscale, but never rushed.
Waipio Valley Lookout on the Big Island of Hawai’i
Hawaiʻi Island – The Big Island
If you’re drawn to raw natural power and diversity, the Big Island delivers. From lava flows and black sand beaches to snow-capped Maunakea, this island feels like five ecosystems in one. Adventure awaits in Hawaiʻi Volcanoes National Park, coffee country in Kona, and lush waterfalls around Hilo. It’s perfect for travelers who want space to roam, cultural richness, and geologic wonders at every turn.
Hawaii Travel Tips
You’ll want to hit the ground running—presumably to the beach!—once you’ve landed. Also be sure to pack a few jackets or hoodies along with your beachwear, as the islands typically has “passing showers” from time to time due to its tropical climate. Another major travel tip to remember is that, unless you’re staying on Oahu, you will absolutely need to rent a car to fully enjoy the best of each island, as public transportation options are limited on the out islands.
More Ways to Save – Insider Tips
- Book mid-week flights (Tuesday or Wednesday) for better fares.
- Travel with a group to split lodging and rental car costs.
- Use loyalty points or credit card rewards to offset airfare or hotel costs.
- Consider hostels, vacation rentals, or condos for more budget-friendly stays.
- Skip the rental car if you’re staying in walkable areas like Waikīkī or Lāhainā.
Affordable Island Adventures
Some of the best things to do in Hawaiʻi are totally free—or just a few bucks:
- Hike to the summit of Diamond Head (Oʻahu)
- Catch the sunrise atop Haleakalā (Maui)
- Explore the colorful cliffs of Waimea Canyon (Kauaʻi)
- Watch lava glow at Hawaiʻi Volcanoes National Park (Big Island)
Your Island Adventure Awaits
Finding cheap vacation packages to Hawaii is all about timing, flexibility, and knowing where to look. With a few insider strategies and a bit of planning, you can enjoy the aloha spirit without overspending.
So pack your sunscreen, your sense of adventure, and your aloha spirit—Hawaii is calling.