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North Side Vacations

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

Hotwire can help you find your travel bliss with North Side 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 North Side

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 North Side 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 North Side well.

Top Hotel Deals

See all 135 Properties in North Side
Ocean Paradise

Ocean Paradise

1234 Rum Point Road, North Side
    4.0 out of 5.0
     
     

    Offering direct access to the beach, this North Side vacation home is in the city center, 0.1 mi (0.1 km) from North Sound, and 1.9 mi (3 km) from Rum Point. ...

    Cayman Dream by Grand Cayman Villas & Condos

    Cayman Dream by Grand Cayman Villas & Condos

    1224 Rum Point Drive, North Side
      3.5 out of 5.0
       
       

      Situated in North Side, this villa is 0.1 mi (0.1 km) from North Sound and 1.9 mi (3 km) from Rum Point. Star Fish Point is 3 mi (4.9 km) away.

      Fantasea by Grand Cayman Villas & Condos

      Fantasea by Grand Cayman Villas & Condos

      288 Water Cay Road, North Side
        3.5 out of 5.0
         
         

        Nestled on the beach, this North Side villa is within a 15-minute walk of North Sound and Rum Point. Star Fish Point and Starfish Beach are also within 1 mi ...

        Casuarina Cove by Grand Cayman Villas & Condos

        Casuarina Cove by Grand Cayman Villas & Condos

        254 Sand Point Road, North Side
          3.5 out of 5.0
           
           

          Nestled on the beach, this North Side villa is just steps from North Sound and Rum Point. Star Fish Point and Starfish Beach are also within 2 mi (3 km).

          Hilltime by Grand Cayman Villas & Condos

          Hilltime by Grand Cayman Villas & Condos

          1738 Rum Point Drive, North Side
            4.0 out of 5.0
             
             

            Nestled on the beach, this North Side villa is within 1 mi (2 km) of North Sound and Rum Point. Star Fish Point and Starfish Beach are also within 3 mi (5 ...

            Heritage House by Grand Cayman Villas & Condos

            Heritage House by Grand Cayman Villas & Condos

            2062 Rum Point Drive, North Side
              3.5 out of 5.0
               
               

              Nestled on the beach, this North Side villa is within a 5-minute walk of North Sound and Rum Point. Star Fish Point and Starfish Beach are also within 2 mi (3 ...

              Kai Zen

              Kai Zen

              442 Water Cay Road, North Side
                3.5 out of 5.0
                 
                 

                Nestled on the beach, this North Side villa is within 1 mi (2 km) of North Sound and Rum Point. Star Fish Point and Starfish Beach are also within 15 ...

                Moon Glow by Grand Cayman Villas & Condos

                Moon Glow by Grand Cayman Villas & Condos

                2090 Rum Point Drive, North Side
                  3.5 out of 5.0
                   
                   

                  Nestled on the beach, this North Side villa is within a 5-minute walk of North Sound and Rum Point. Star Fish Point and Starfish Beach are also within 2 mi (3 ...

                  Coral Cottage Pink by Grand Cayman Villas & Condos

                  Coral Cottage Pink by Grand Cayman Villas & Condos

                  325B Old Robin Road, North Side
                    3.5 out of 5.0
                     
                     

                    This Old Man Bay villa is on the beach, 2.1 mi (3.4 km) from Mastic Trail North Trailhead, and within 6 mi (10 km) of Queen Elizabeth II Botanic Park and North ...

                    Pools of the Kai 6 by Grand Cayman Villas & Condos

                    Pools of the Kai 6 by Grand Cayman Villas & Condos

                    6 Kaibo Crescent, North Side
                      3.5 out of 5.0
                       
                       

                      Situated near the beach, this villa is 0.1 mi (0.1 km) from North Sound and 1.4 mi (2.2 km) from Rum Point. Star Fish Point and Starfish Beach are also within ...

                      Top Flight Deals

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