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Kailua Vacations

Pack those stellar shades. We have Kailua vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Kailua – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Kailua vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Kailua

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Kailua vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Kailua well.

Kailua Flight + Hotel packages

Top Hotel Deals

See all 519 Hotels in Kailua
Maui Seaside Hotel

Maui Seaside Hotel

100 W Kaahumanu Ave, Kahului
    2.5 out of 5.0
     
     

    Across from Kaahumanu Center, the hotel is within 3 miles of the airport, downtown Kahului, and Wailuku, and within 7 miles of Kihei beaches. The hotel is also ...

    Maui Seaside Hotel$169

    Maui Seaside Hotel$169
    Luana Kai Resort

    Luana Kai Resort

    940 S. Kihei Road, Kihei
      3.0 out of 5.0
       
       

      Offering direct access to the beach, this Kihei condo building is within a 10-minute walk of Waipuilani Park and Kalepolepo. Maui Nui Golf Club and Kihei Regional ...

      CRH- Sugar Beach Resort

      CRH- Sugar Beach Resort

      145 N. Kihei Road, Kihei
        3.0 out of 5.0
         
         

        Nestled on the beach, this Kihei condo building is within 2 mi (3 km) of Kealia Pond National Wildlife Refuge, Maalaea Beach, and Kalepolepo. Waipuilani Park ...

        Maui Beach Hotel

        Maui Beach Hotel

        170 Kaahumanu Avenue, Kahului
          2.5 out of 5.0
           
           

          Tikis dot the lawn of this Maui hotel, right on the harbor in Kahului, Hawaii, 2 miles from Kahana Beach Park, and 5 miles from Iao Valley State Park. Kahului ...

          Maui Beach Hotel$119

          Maui Beach Hotel$119
          Courtyard Maui Kahului Airport

          Courtyard Maui Kahului Airport

          532 Keolani Place, Kahului
            3.5 out of 5.0
             
             

            Situated near the airport, this hotel is within 3 mi (5 km) of Kanaha Beach Park, Maui Arts and Cultural Center, and Maui Nui Botanical Gardens. Alexander and ...

            Courtyard Maui Kahului Airport$259

            Courtyard Maui Kahului Airport$259
            Maui Schooner Resort

            Maui Schooner Resort

            980 S Kihei Rd, Kihei
              3.5 out of 5.0
               
               

              Nestled on the beach, this Kihei condo building is within a 10-minute walk of Kalepolepo and Waipuilani Park. Maui Nui Golf Club and Kihei Regional Park are ...

              Lumeria Maui an Educational Experience

              Lumeria Maui an Educational Experience

              1813 Baldwin Ave, Makawao
                3.5 out of 5.0
                 
                 

                Located in the heart of Makawao, this spa hotel is within 6 mi (10 km) of Lower Paia Park, Hookipa Beach Park, and H.A. Baldwin Beach State Park. Maui Arts and ...

                Lumeria Maui an Educational Experience$269

                Lumeria Maui an Educational Experience$269
                The Old Wailuku Inn at Ulupono

                The Old Wailuku Inn at Ulupono

                2199 Kaho'okele Street, Wailuku
                  3.0 out of 5.0
                   
                   

                  Situated in Wailuku, this bed & breakfast is 0.5 mi (0.8 km) from Bailey House Museum and within 3 mi (5 km) of Maui Nui Botanical Gardens and Maui Arts and ...

                  Travaasa Hana, Maui

                  Travaasa Hana, Maui

                  5031 Hana Hwy, Hana
                    4.0 out of 5.0
                     
                     

                    Set amid the picturesque oceanfront community of "Heavenly Hana" on Maui's secluded eastern shore, this resort is close to Hamoa Beach.

                    Travaasa Hana, Maui$525

                    Travaasa Hana, Maui$525
                    Maui Sunset

                    Maui Sunset

                    1032 S Kihei Rd, Kihei
                      3.5 out of 5.0
                       
                       

                      Nestled on the beach, this Kihei condo building is within a 15-minute walk of Waipuilani Park and Kalepolepo. Maui Nui Golf Club and Kihei Regional Park are ...

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.