Kailua Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Kailua

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

Paradise Bay Resort

Kahaluʻu
Save 100% on your flight
€980
per person
10 Dec - 16 Dec
found 1 day ago
Return flight included
San Francisco (SFO) to Honolulu (HNL)
8.8/10 Excellent! (1,006 reviews)
This place is gorgeous! I am a native to Oahu and wanted to staycation for my anniversary. Didn't want to do the Waikiki stay, and I've always seen this resort but they never have availability! Just so happen, the dates worked and I was in awe from the moment I got here. Everything is so open and connected to nature. The room was perfect, with a full kitchen and dishes / cookware are all included! Resort fee includes free rentals of snorkeling equipment, kayaks (single & double), paddle boards, and on Saturday from 10am-2pm they offer a ride out to the sandbar on their boat! The pool and jacuzzi were amazing! The banana bread and coffee in the main area were really yummy. Ice machine right outside our room, next to our car that we parked literally feet from the front door to our room. Gorgeous nature scenery in every direction! Unit 61 is a corner unit on the top floor overlooking the pool and the canal that leads to the ocean. Kayaking out to the little island was cute but water was a bit choppy today. The little waterfalls that they have stationed all.over the property make everything sound so serene. We will.definitely be back for future staycations!

Reviewed on 20 Sept 2026

Stay Hotel Waikiki

Stay Hotel Waikiki

Waikiki
Save 100% on your flight
€1,092
per person
10 Dec - 16 Dec
found 1 day ago
Return flight included
San Francisco (SFO) to Honolulu (HNL)
8.2/10 Very good! (1,994 reviews)
We had the loveliest stay. The staff were kind and accommodating. The rooms were modest but fulfilled exactly what we needed in a fantastic location. A great little room at a great price that made our trip so easy!

Reviewed on 22 Sept 2026

OUTRIGGER Waikiki Beach Resort

OUTRIGGER Waikiki Beach Resort

Waikiki
Save 100% on your flight
€1,474
per person
10 Dec - 16 Dec
found 1 day ago
Return flight included
San Francisco (SFO) to Honolulu (HNL)
9/10 Wonderful! (3,544 reviews)
After a long trip that had to be changed from going to Kauai at the last minute, the outrigger beach resort gave us the best alternate vacation. The staff was so friendly and accommodating, the property is right on the beach pool side service on point and great food was had at Dukes and the Hula grill. Prime location on Waikiki.

Reviewed on 22 Sept 2026

Luana Waikiki Hotel & Suites

Luana Waikiki Hotel & Suites

Waikiki
Save 100% on your flight
€1,272
per person
10 Dec - 16 Dec
found 1 day ago
Return flight included
San Francisco (SFO) to Honolulu (HNL)
8.8/10 Excellent! (1,679 reviews)
Due to the recent storm come by Waikīkī , the property has minor damage and could use a little tune up. Furniture could also need to be update to 2026. Staffing was awesome and helpful.

Reviewed on 22 Sept 2026

OUTRIGGER Reef Waikiki Beach Resort

OUTRIGGER Reef Waikiki Beach Resort

Waikiki
Save 100% on your flight
€1,327
per person
10 Dec - 16 Dec
found 1 day ago
Return flight included
San Francisco (SFO) to Honolulu (HNL)
9.4/10 Exceptional! (3,166 reviews)
Great stay....clean, comfy relaxing

Reviewed on 22 Sept 2026

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 may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lanikai Beach and Lanikai Pillboxes Trailhead.

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

While there might not be top attractions in Beachside, you can explore the larger area and discover places like Kailua Beach and Lanikai Pillboxes Trailhead.

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

Enchanted Lake

While Enchanted Lake may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lanikai Pillboxes Trailhead and Kailua Beach.

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

When in Kalama Tract, you can plan a visit to Kailua Bay Beach and Kailua Beach, some noteworthy sights in the nearby area.

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.

Things to do in and around Kailua

Kailua is ideal for outdoor family holidays, offering a variety of activities such as exploring the area, kayaking, and kite surfing. Visitors can also enjoy the local shopping mall and a thrilling zipline ropes course. With its stunning scenery and numerous sports activities, Kailua provides a perfect blend of adventure and relaxation for an unforgettable Hawaiian experience.

Shopping

Kailua offers a delightful shopping experience with Windward Mall, just 6.4km away, featuring a variety of shops and family-friendly vibes. If you're up for a drive, Kahala Mall, located 14.5km away, provides a vibrant mix of entertainment and city atmosphere, while Kapi'olani Community College Farmers' Market is also worth visiting at 16.1km away.

Recreation

At Kaiona Beach Park, enjoy tranquil beach walks and serene picnics amid nature's beauty, only 9.7km from Kailua. Olomana Golf, just 4.8km away, offers invigorating rounds of golf with picturesque views. Kawaikui Beach Park, 14.5km distant, provides a peaceful retreat for relaxation and rejuvenation.

Adventure

Embark on the Olomana Three Peaks Trail for stunning views and thrilling hikes. Explore the Lanikai Pillboxes Trailhead, where scenic landscapes await. For a refreshing adventure, trek to Lulumahu Waterfall, located 9.7km from Kailua, and immerse yourself in nature's beauty.

Nightlife

Kailua's nightlife is relaxed yet vibrant, featuring beachside bars and intimate venues. Enjoy cocktails at the Buzz's Lanikai, or catch live music at the Kailua Town Pub. For a laid-back evening, stroll along the shore, soaking in the tropical atmosphere under the stars.

*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 is an ideal destination for outdoor and family beach holidays, offering a delightful mix of attractions. Visitors can enjoy the stunning Kailua Beach, explore the scenic Kailua Bay Beach, and engage in surfing activities at Oahu's renowned spots. With its focus on beach, outdoor experiences, and cultural encounters, Kailua promises a memorable getaway for all types of travellers seeking relaxation and adventure by the sea.

  • Lanikai Beach: Renowned for its soft, powdery sands and crystal-clear waters, Lanikai Beach offers a quintessential Hawaiian beach experience. The tranquil atmosphere is perfect for sunbathing, swimming, and kayaking, making it a favourite among locals and tourists alike. The stunning views of the Mokulua Islands add to its charm, providing a picturesque backdrop for relaxation.
  • Hanauma Bay Nature Preserve: A marine sanctuary famed for its vibrant coral reefs and diverse marine life, Hanauma Bay is the ideal spot for snorkelling enthusiasts. The friendly vibe of the area is complemented by educational programmes that promote conservation, allowing visitors to connect with nature while enjoying its beauty.
  • Mokapu Point: Offering breathtaking panoramic views, Mokapu Point is a captivating cape perfect for sightseeing. Visitors can enjoy scenic walks along the coastline while taking in the surrounding beaches and lush landscapes, making it a tranquil escape within Kailua.

Best time to go to Kailua

The best time to visit Kailua can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Kailua falls in September, when visitor numbers are average and weather is mostly sunny with no rain. The coolest average temperature in Kailua falls in February, 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 SunnyAverageSlightly High
July77.9°F (25.5°C)No RainMostly SunnySlightly HighSlightly High
August78.4°F (25.8°C)No RainMostly SunnyAverageAverage
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 to Kailua during the low season (May and October to November) for more affordable options.
  • 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 Holiday

Kick back on the shoreline as you admire the sunlight flickering across the water during your Kailua holiday. 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 organising your accommodation 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.

Top hotels in Kailua

Hilton Hawaiian Village Waikiki Beach Resort

Hilton Hawaiian Village Waikiki Beach Resort

2005 Kalia Rd Honolulu HI
Fully refundableReserve now, pay when you stay
€302
1 Oct - 2 Oct
includes taxes & fees
8.4/10 Very good! (9,876 reviews)
"We stayed in the diamond head tower-it is outdated the bath towels were stained and the bed sheets seemed worn. It needs to be a microwave in the suites at least and a shower curtain up in the bathroom. I was not impressed with the room amenities at all. The overall appearance of the resort was ..."

Reviewed on 22 Sept 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
€325
23 Sept - 24 Sept
includes taxes & fees
9/10 Wonderful! (5,423 reviews)
"This place was everything! It was so beautiful, so clean, the staff was wonderful, and everything was right there at the hotel. Including an amazing tattoo shop. We will be staying here from now on."

Reviewed on 21 Sept 2026

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
€306
27 Sept - 28 Sept
includes taxes & fees
9.2/10 Wonderful! (3,577 reviews)
"This place is located right on the right location, their Staff is very professional and friendly. The rooms are clean and kept well organized. The pool Staff were very attentive, kept an eye around the pools to keep all of us saved. They were super friendly, one day I stayed away from the pool and ..."

Reviewed on 22 Sept 2026

Sheraton Waikiki Beach Resort
See all 5,739 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.

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)
Lanikai Beach captivates with powdery white sand and crystal-clear turquoise waters framing the iconic Mokulua Islands. Arrive early for the breathtaking sunrise on this serene stretch of paradise.
See properties
Two people kayaking on turquoise waters with clear skies and two small islands in the background.
Photo by Hawaii Visitors and Convention Bureau

Kailua Beach

9.2/10 (4,483 reviews)
Kailua Beach enchants with its powdery white sand and crystal-clear turquoise waters perfect for swimming. Rent a kayak to paddle out to the picturesque Mokulua Islands for an unforgettable adventure.
See properties
A beach with clear turquoise water, people swimming and sunbathing, and lush green hills in the background.

Kailua Bay Beach

9.8/10 (9 reviews)
Kailua Beach captivates with powdery white sand and crystalline turquoise waters ideal for water sports. Kayak to the nearby Mokulua Islands or try windsurfing in the steady trade winds.
See properties
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 offers gentle waves perfect for beginner surfers and bodyboarders in a tranquil setting. Enjoy the shady spots under native trees while watching kiteboarders harness the favourable winds.
See properties
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)
This historic WWII trail offers breathtaking 360-degree views of Lanikai Beach and the Mokulua Islands. Arrive at sunrise to witness golden light illuminating the Ko'olau Mountains from the pillbox vantage points.
See properties
A golf course with a view of the ocean and mountains in the background.

Kaneohe Klipper Golf Course

6.0/10 (1 review)
This oceanfront military golf course winds along Oahu's coastline with stunning Pacific and Ko'olau Mountain views. Play challenging holes right at the water's edge while enjoying one of Hawaii's most scenic courses.
See properties
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?
See properties

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.
See properties

What to do in Kailua

Waikiki Trolley Pass All Line Hop-On Hop-Off

Waikiki Trolley Pass All Line Hop-On Hop-Off

€15
per adult
94% of travellers recommend
Waikiki Trolley Pass All Line Hop-On Hop-Off
Cruise Ship at sea in Oahu

Sunset Dinner Cruise with Polynesian Show

€90
per adult
86% of travellers recommend
Sunset Dinner Cruise with Polynesian Show
Ultimate Pearl Harbor Circle Island

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

€113
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 holiday package cost?
You'll find cheap prices from €980 on Expedia for your Kailua break. However, a range of factors like the season, choice of hotel and length of stay will determine how much your holiday to Kailua costs.
What are the cheapest months to go to Kailua?
If you'd like to score a cheap Kailua holiday package, consider visiting in April, June and November. You'll usually find lower prices on flights and hotels during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Kailua?
We'd recommend booking a Kailua holiday for a minimum of 6 days. This gives you plenty of time to check off popular sights such as Kailua Bay Beach and Kalama Beach Park, as well as explore neighbourhoods like Lanikai and Kalama Tract. You could even fit in a day trip (or two) from Kailua.
Is it worth booking a holiday package to Kailua?
Kailua has all the ingredients you need for an awesome trip — distilleries and craft breweries, golfing and hiking are just the start. Whether you'd like to check out attractions like Lanikai Beach and Kailua Beach, or venture off the beaten track, there's plenty to explore on your Kailua holiday.
How to find the best Kailua package deals?
Begin your search for a Kailua package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Kailua package deal straight away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Kailua getaway off to a flying start.
Is it cheaper to book a Kailua holiday as a package?
You can enjoy significant savings on your Kailua escape by booking a tailored holiday package. Click on the "Package" heading, then enter your destination and travel dates to browse some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Kailua?
If you're considering a spur-of-the-moment Kailua trip, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Kailua?
  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Kailua.
  2. Plan your budget wisely: In addition to the cost of your accommodation, you should consider other expenses too. These include food, transportation and flights. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Kailua.
  3. Decide how long to go away for: Now that you're more familiar with Kailua, you can work out the perfect length of your break. Pull together a rough plan and give yourself enough time to cover everything you want to do.
  4. Bundle your airfare and accommodation: After you've nailed down your trip dates and duration, lock in the ideal Kailua holiday package for you.

Explore a world of travel with Expedia

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