Kailua Vacation Packages

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Your Kailua Vacation

From its highlights to its hidden delights, this city is best experienced with a Kailua vacation package. Find a place to stay in Waikiki, which is great for nightlife, coastal beaches and cafes. If taking in sights is part of the program during your trip to Kailua, check out major attractions like Kailua Beach, Lanikai Beach and Waimanalo Beach. Expedia is here to help you escape your routine. Tailor your vacation to Kailua to suit your travel style, whatever that may look like.

Top Kailua Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Paradise Bay Resort

Paradise Bay Resort

Kahaluʻu
Save 100% on your flight
CA $1,495
per person
Dec 2 - Dec 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Honolulu (HNL)
8.8/10 Excellent! (1,007 reviews)
We booked a mountain view studio with a kitchenette for three nights. The photos on the website make the rooms look so much nicer than in person. The rooms are dated and, with just a little bit of investment, could be so much nicer... and could possibly live up to the 4 star rating. The view from the harbor view rooms is truly lovely. Our mountain view room had minimal mountain, but when I sat on the balcony with my morning coffee, I could see a bit of the bay. And the view from the lobby and reception area was great. Each morning, there was coffee, fruit, and banana bread, and one can sit there and look at the bay, the mountains, and the chickens! Or bring your coffee to the floating dock and enjoy the bay from there. The service was good, requests for a couple of things were quickly met, while a request for towels took a bit of time. The kitchenette was simply, but adequately, stocked. We were on the go during our stay on Oahu, so did not use the amenities, but would have loved to kayak on the calm waters. I would recommend this hotel, for the location and the views. Our expectations on a 'resort room' were higher than they should have been, but as long as you know, then you will not be disappointed. Aloha and mahalo.

Reviewed on Oct 11, 2026

Ilikai by Luana Hawaii Vacation Rentals

Ilikai by Luana Hawaii Vacation Rentals

Waikiki
CA $1,807
per person
Dec 4 - Dec 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Honolulu (HNL)
8.8/10 Excellent! (61 reviews)
We had 3 adults staying there. It was advertised for 3 adults, however, the futon foldout was only big enough for a kid. We took pictures of our adult kids and their heads went over the futon. However. After complaining, the owners dropped off a double/queen blow up mattress, about the 3 day into the stay, meanwhile one of the kids had to move into our room. So, bad news, the room was not set up for 3 adults, but good news after days of complaining, the bed was corrected.

Reviewed on Aug 27, 2026

Ala Moana Hotelcondo by Luana Vacation Rental

Ala Moana Hotelcondo by Luana Vacation Rental

Ala Moana
Save 100% on your flight
CA $2,174
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Honolulu (HNL)
7.6/10 Good! (258 reviews)
@ Marbella Lane - Paradise Point Close to Beaches

@ Marbella Lane - Paradise Point Close to Beaches

Save 100% on your flight
CA $10,746
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Honolulu (HNL)
10/10 Exceptional! (1 review)
Everything was perfect! Thank you to the Marbella Team, our stay was excellent. We enjoyed everything Mākaha valley had to offer. Especially the amazing sunsets! 10/10 would recommend

Reviewed on Dec 24, 2025

Sheraton Waikiki Beach Resort

Sheraton Waikiki Beach Resort

Waikiki
Save 100% on your flight
CA $3,400
per person
Dec 19 - Dec 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Honolulu (HNL)
9.2/10 Wonderful! (3,624 reviews)

Where to stay in Kailua

Find the best Kailua areas and neighborhoods for the activities you enjoy most. Learn more about Kailua
A tropical beach with clear turquoise waters, two small islands, and a dense palm tree line.

Lanikai

1 out of top 10 points of interest in this area

While Lanikai isn't home to many top sights, Lanikai Beach and Kailua Beach are some notable places to visit nearby.

Find hotels in Lanikai
A coastal town with a clear view of the ocean, a hilly landscape, and a distant mountain range.

Beachside

1 out of top 10 points of interest in this area

Though Beachside might not have many top sights, you can venture to the surrounding area to see attractions like Kailua Beach and Lanikai Beach.

Find hotels in Beachside
A beach at sunset with two prominent rock formations in the distance and a vibrant sky.

Enchanted Lake

When in Enchanted Lake, you can plan a visit to Kailua Beach and Lanikai Beach, some noteworthy sights in the nearby area.

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A beach at night with a cloudy sky, palm trees, and distant mountains.

Kalama Tract

2 out of top 10 points of interest in this area

While Kalama Tract might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Kailua Bay Beach and Kailua Beach.

Find hotels in Kalama Tract
A couple walking on a beach with two prominent mountains in the background.

Coconut Grove

1 out of top 10 points of interest in this area

While Coconut Grove isn't home to many top sights, Kailua Bay Beach and Kailua Beach are some notable places to visit nearby.

Find hotels in Coconut Grove

Things to do in and around Kailua

Kailua is perfect for a family beach vacation, offering a range of outdoor activities. Enjoy exploring the vibrant shopping mall centre, or take on the excitement of a zipline ropes course. Don't miss the stunning Kailua Beach for a memorable beach experience, and consider a day trip to soak in the sun and surf. This lovely destination promises a blend of relaxation and adventure for all visitors.

Shopping

In Kailua, enjoy shopping at Windward Mall, just 6.4km away, offering a family-friendly atmosphere. You can also visit the Kapi'olani Community College Farmers' Market, located 16.1km away, for local produce and crafts. If you're up for a drive, Kahala Mall, 14.5km away, features entertainment and shopping options.

Recreation

Experience a round of golf at Pali Golf Course, just 4.8km from Kailua, offering lush landscapes and a vibrant outdoor atmosphere. Alternatively, unwind at Kaiona Beach Park, located 9.7km away, where wellness and relaxation await amidst stunning coastal views. Don't miss the scenic Ko'olau Golf Club, 6.4km from Kailua.

Adventure

Experience the thrill of the Olomana Three Peaks Trail, where breathtaking views await. Hike the Lanikai Pillboxes Trailhead for stunning coastal scenery. For a more secluded adventure, trek to Lulumahu Waterfall, located 9.7km from Kailua, and immerse yourself in the lush Hawaiian landscape.

Nightlife

Kailua's nightlife offers a relaxed vibe with beachside bars and local eateries. Enjoy craft cocktails at Haleiwa Joe's or unwind at Buzz's Lanikai. For live music, check out the nearby venues that showcase local talent, creating a vibrant atmosphere perfect for a memorable evening.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Kailua

Kailua, located in Honolulu County, Hawaii, is perfect for outdoor and family beach vacations. Visitors can enjoy beautiful spots like Kailua Beach Park and the stunning Kailua Beach, while exploring attractions such as Kailua Town and the picturesque sand beaches. With its emphasis on outdoor activities and scenic experiences, Kailua offers something for every traveller seeking a memorable getaway.

  • Lanikai Beach: Renowned for its breathtaking beauty, Lanikai Beach boasts powdery white sands and crystal-clear waters. The serene atmosphere makes it perfect for sunbathing, swimming, and kayaking, offering an idyllic beach vibe that feels like a slice of paradise.
  • University of Hawaii at Manoa: This vibrant campus, located 14.5km from Kailua, showcases modern architecture and rich cultural diversity. With its lush landscapes and engaging academic environment, it offers a unique city vibe, inviting visitors to explore its gardens and museums.
  • Kaneohe Bay: Just 4.8km from Kailua, Kaneohe Bay captivates with stunning scenery and outdoor activities. Enjoy kayaking, paddleboarding, or simply relaxing by the water while taking in the panoramic views of the surrounding mountains and islands.

Best time to go to Kailua

The best time to visit Kailua is dependent on what kind of holiday you are seeking. September is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with no rain. February is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January73.4°F (23.0°C)No RainMostly SunnyAverageAverage
February72.7°F (22.6°C)No RainMostly SunnyAverageAverage
March72.9°F (22.7°C)Light RainMostly SunnySlightly HighAverage
April74.1°F (23.4°C)No RainMostly SunnySlightly HighAverage
May75.6°F (24.2°C)No RainMostly SunnyAverageSlightly Low
June77.0°F (25.0°C)No RainMostly SunnyAverageAverage
July77.9°F (25.5°C)No RainMostly SunnySlightly HighSlightly High
August78.4°F (25.8°C)No RainMostly SunnyAverageSlightly High
September78.8°F (26.0°C)No RainMostly SunnyAverageAverage
October78.3°F (25.7°C)No RainMostly SunnySlightly LowSlightly Low
November76.5°F (24.7°C)No RainMostly SunnySlightly LowSlightly Low
December74.5°F (23.6°C)Light RainMostly SunnySlightly LowSlightly High

Tips to save on your trip to Kailua

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Kailua.
  • Consider traveling during the off-peak season (typically May and October to November) for more affordable package holidays to Kailua.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Kailua Beach Vacation

Kick back on the shoreline as you admire the sunlight flickering across the water during your Kailua vacation. If you're looking for a full beach experience, a trip to Kailua will deliver. You've probably heard about Lanikai Beach (3 kilometres away). We suggest organizing your accommodations nearby. However, many sightseers also go for Kailua packages that are closer to Kailua Bay Beach or Kalama Beach Park, two other great nearby options.

Ready to book your vacation to Kailua?

Choose your dates

Kailua Hotel Deals

Hilton Hawaiian Village Waikiki Beach Resort

Hilton Hawaiian Village Waikiki Beach Resort

2005 Kalia Rd Honolulu HI
Fully refundableReserve now, pay when you stay
CA $338
CA $494 total
Oct 29 - Oct 30
includes taxes & fees
8.4/10 Very good! (10,028 reviews)
"Room was outdated. Property and amenities were good"

Reviewed on Oct 12, 2026

Hilton Hawaiian Village Waikiki Beach Resort
Hyatt Regency Waikiki Beach Resort & Spa

Hyatt Regency Waikiki Beach Resort & Spa

2424 Kalakaua Ave Honolulu HI
Fully refundableReserve now, pay when you stay
CA $384
CA $548 total
Oct 13 - Oct 14
includes taxes & fees
Hyatt Regency Waikiki Beach Resort & Spa
Sheraton Waikiki Beach Resort

Sheraton Waikiki Beach Resort

2255 Kalakaua Ave Honolulu HI
Fully refundableReserve now, pay when you stay
CA $348
CA $501 total
Oct 29 - Oct 30
includes taxes & fees
Sheraton Waikiki Beach Resort
See all 5,744 properties in Kailua
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Kailua attractions

A beach with clear turquoise water, a sandy shore, and several boats lined up on the right.

Lanikai Beach

9.2/10 (3,293 reviews)
Why not spend a carefree afternoon at Lanikai Beach during your travels in Kailua? You can seek out the snorkeling spots while in the area.
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A coastal town with houses, palm trees, and two prominent islands in the ocean.

Kailua Beach

9.2/10 (4,483 reviews)
With just-right waves and refreshing breezes, this is one of the best beaches on O’ahu to learn how to windsurf or kitesurf.
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A coastal walkway lined with palm trees, a rocky shoreline, and a clear view of the ocean.

Kalama Beach Park

9.2/10 (5 reviews)
Kalama Beach Park is just one of the places to see in Kailua, so why not enjoy the other things to explore during your travels? Wander the parks and beaches while you're in the area.
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A golf course with a view of the ocean and mountains in the background.

Kaneohe Klipper Golf Course

6.0/10 (1 review)
Enjoy a round of golf in Marine Corps Base Hawaii at Kaneohe Klipper Golf Course. Visit the area's shops or amble around its beautiful beaches.
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A coastal town with clear blue waters, two small islands, and a dense cluster of houses and palm trees.

Lanikai Pillboxes Trailhead

9.4/10 (6 reviews)
You can take time to visit Lanikai Pillboxes Trailhead during your travels to Kailua. Stroll along the area's seaside, or simply savor its top-notch restaurants.
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A beach with clear turquoise water, a sandy shore, and two small islands in the distance during sunset.

Kalama Beach

Why not spend a lazy afternoon at Kalama Beach during your trip to Kailua?
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Mokapu Point

10.0/10 (2 reviews)
Commune with nature and explore the great outdoors at Mokapu Point during your travels in Marine Corps Base Hawaii. Wander the beautiful beaches in this relaxing area.
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Kawainui Park

After visiting Kawainui Park, make a plan to see the other sights and activities in Kailua. Add the area's shops or temples to your travel plans.
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What to do in Kailua

Cruise Ship at sea in Oahu

Sunset Dinner Cruise with Polynesian Show

CA $146
per adult
86% of travellers recommend
Sunset Dinner Cruise with Polynesian Show
Turtle near reef in Oahu

Turtle Canyon Snorkel Catamaran Cruise from Hilton Hawaiian Village Pier

CA $154
per adult
88% of travellers recommend
Turtle Canyon Snorkel Catamaran Cruise from Hilton Hawaiian Village Pier
Ultimate Pearl Harbor Circle Island

Ultimate Circle Island Tour with Pearl Harbor Dole Plantation & USS Arizona

CA $183
per adult
92% of travellers recommend
Ultimate Circle Island Tour with Pearl Harbor Dole Plantation & USS Arizona
See all activities in Kailua

Frequently asked questions

How much does a Kailua vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,495 on Expedia. But how much your vacation to Kailua costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Kailua?
April, June and November are great times to search for cheap Kailua vacation packages. Travelling in quieter months means you can generally find reduced prices on accommodations and flights.
How many days is enough for Kailua?
Kailua vacations can be short or long, but to get a true feel for this place, we'd suggest 6 days is a good ballpark. This will mean you can visit top attractions like Waimanalo Beach and Kaneohe Bay and track down some hidden gems. Don't skip cool areas such as Lanikai and Kalama Tract either. If you're clever with your time, you may even be able to take a day trip outside of Kailua too.
Is it worth booking a vacation package to Kailua?
Kailua has everything you need for the perfect getaway — distilleries and craft breweries, golfing and hiking are just the start. Whether you want to check out attractions like Lanikai Beach and Kailua Beach, or take the road less travelled, you'll have plenty to do on your Kailua vacation.
How to find the best Kailua package deals?
Finding a cheap Kailua package deal is a breeze with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply some filters and browse what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Kailua package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Kailua vacation as a package?
You can enjoy significant savings on your Kailua escape by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to view some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Kailua?
If you're considering a spur-of-the-moment Kailua vacation, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Kailua?
  1. Choose when to get away: Check your diary and get your bags packed. Your favourite time of year and the activities on offer will also help you decide when to visit Kailua.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and meals to experiences and flights. Your accommodations will probably be the largest expense during your trip to Kailua.
  3. Decide how long to go away for: Now that you know more about Kailua, you can figure out the ideal length of your break. Create a rough plan and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Kailua vacation package.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.