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Olowalu Vacations

Pack those stellar shades. We have Olowalu 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 Olowalu – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Olowalu 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 Olowalu

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 Olowalu 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 Olowalu well.

Olowalu Flight + Hotel packages

Top Hotel Deals

See all 3,150 Hotels in Olowalu
Royal Lahaina Resort

Royal Lahaina Resort

2780 Kekaa Dr, Lahaina
    3.5 out of 5.0
     
     

    Royal Lahaina Resort is set on 27 acres and arrayed along 2 championship golf courses. The resort faces a scenic stretch of West Maui's famed Kaanapali Beach; ...

    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
      Four Seasons Resort Maui at Wailea

      Four Seasons Resort Maui at Wailea

      3900 Wailea Alanui Drive, Kihei
        5.0 out of 5.0
         
         

        Located on Maui's sunny south shore, this resort faces the wide, crescent curve of Wailea Beach, with its sugar sands and calm waters. The Wailea Blue golf course ...

        Four Seasons Resort Maui at Wailea$559

        Four Seasons Resort Maui at Wailea$559
        Aston Kaanapali Shores

        Aston Kaanapali Shores

        3445 Lower Honoapiilani Hwy, Lahaina
          3.5 out of 5.0
           
           

          Aston Kaanapali Shores is located on Maui's sunny west shore in north Kaanapali, 4 miles from historic Lahaina and within 5 miles of the championship golf courses ...

          Aston Kaanapali Shores$225

          Aston Kaanapali Shores$225
          Maui Coast Hotel

          Maui Coast Hotel

          2259 S Kihei Rd, Kihei
            3.5 out of 5.0
             
             

            Surrounded by shops and restaurants, this seven-story hotel is across the street from Kamaole Beach Park I, 3 miles from upscale Wailea, and 7 miles from Maui ...

            Maui Coast Hotel$141

            Maui Coast Hotel$141
            Kaanapali Beach Hotel

            Kaanapali Beach Hotel

            2525 Kaanapali Parkway, Lahaina
              3.0 out of 5.0
               
               

              Called Hawaii's "Most Hawaiian Hotel," the 11-acre beachfront Kaanapali Beach Hotel is a quarter-mile from Whalers Village, a half-mile from Kaanapali Golf Course, ...

              Kaanapali Beach Hotel$207

              Kaanapali Beach Hotel$207
              Wailea Beach Resort - Marriott, Maui

              Wailea Beach Resort - Marriott, Maui

              3700 Wailea Alanui Dr, Kihei
                4.5 out of 5.0
                 
                 

                Cradled against an oceanfront hillside, this expansive, low-rise Maui hotel lies a minute's walk from beaches and a quarter-mile from the Shops at Wailea; 3 ...

                Wailea Beach Resort - Marriott, Maui$351

                Wailea Beach Resort - Marriott, Maui$351
                Aston Maui Kaanapali Villas

                Aston Maui Kaanapali Villas

                45 Kai Ala Dr, Lahaina
                  3.0 out of 5.0
                   
                   

                  Directly on one of the finest stretches of Kaanapali Beach, the Aston Maui Kaanapali Villas is set on 11 acres of exotic tropical gardens in the Kaanapali Resort ...

                  Aston Maui Kaanapali Villas$239

                  Aston Maui Kaanapali Villas$239
                  Hyatt Regency Maui Resort & Spa

                  Hyatt Regency Maui Resort & Spa

                  200 Nohea Kai Dr, Lahaina
                    4.0 out of 5.0
                     
                     

                    Situated on 40 lush, beachfront acres, Hyatt Regency Maui Resort & Spa is across from Kaanapali's 2 championship golf courses, a half-mile from Whalers Village ...

                    Hyatt Regency Maui Resort & Spa$299

                    Hyatt Regency Maui Resort & Spa$299
                    Fairmont Kea Lani Maui

                    Fairmont Kea Lani Maui

                    4100 Wailea Alanui Dr, Kihei
                      4.5 out of 5.0
                       
                       

                      Set amid waterfall gardens, pools, and Polo Beach, this 22-acre oceanfront resort borders Wailea's 3 championship golf courses and is 1 mile (1.6 kilometers) ...

                      Top Flight Deals

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