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Pico Island Vacations

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

Hotwire can help you find your travel bliss with Pico Island 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 Pico Island

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 Pico Island 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 Pico Island well.

Top Hotel Deals

See all 93 Properties in Pico Island
Aldeia das Adegas

Aldeia das Adegas

Rua das Adegas 3A, Sao Roque do Pico
    4.0 out of 5.0
     
     

    Situated near the beach, this apartment building is within 1 mi (2 km) of Convent of Sao Roque do Pico and Sao Roque Church. Caiado Lagoon and Museu do Vinho ...

    Aldeia das Adegas$133

    Aldeia das Adegas$133
    Sara Village

    Sara Village

    Estrada Regional Nº1 Nº20, Sao Roque do Pico
      3.0 out of 5.0
       
       

      Situated in Sao Roque do Pico, this country house is 0.4 mi (0.7 km) from Sao Roque Church and 1.5 mi (2.4 km) from Convent of Sao Roque do Pico. Caiado Lagoon ...

      Sara Village$87

      Sara Village$87
      AL-NovaVista

      AL-NovaVista

      Rua Nova n 8, Madalena
        3.0 out of 5.0
         
         

        Situated in Madalena, this aparthotel is 1 mi (1.6 km) from Pico Island Vineyard Culture and within 3 mi (5 km) of Gruta das Torres and Museu do Vinho. Horta ...

        AL-NovaVista$100

        AL-NovaVista$100
        Casa das Barcas

        Casa das Barcas

        Rua Do Cais, Sao Roque do Pico
          3.0 out of 5.0
           
           

          Situated in Sao Roque do Pico, this bed & breakfast is within 1 mi (2 km) of Convent of Sao Roque do Pico and Sao Roque Church. Caiado Lagoon and Museu do Vinho ...

          Casa do Comendador

          Casa do Comendador

          Rua de Baixo, No 17 S.Miguel Arcanjo, Sao Roque do Pico
            4.0 out of 5.0
             
             

            Situated by the ocean, this guesthouse is 1.2 mi (1.9 km) from Sao Roque Church and 2.4 mi (3.8 km) from Convent of Sao Roque do Pico. Caiado Lagoon is 11.3 ...

            Casa do Comendador$96

            Casa do Comendador$96
            Aldeia da Fonte Hotel-Apartamentos

            Aldeia da Fonte Hotel-Apartamentos

            Caminho Da Fonte Silveira, Lajes do Pico
              4.0 out of 5.0
               
               

              Situated by the ocean, this eco-friendly hotel is 2.5 mi (4 km) from Lajes Whaling Museum and 9.4 mi (15.2 km) from Caiado Lagoon. Convent of Sao Roque do Pico ...

              Aldeia da Fonte Hotel-Apartamentos$87

              Aldeia da Fonte Hotel-Apartamentos$87
              Aldeia dos Caldeirões

              Aldeia dos Caldeirões

              Rua dos Caldeirões, Madalena
                 
                 

                Situated in the mountains, this vacation home is within 9 mi (15 km) of Gruta das Torres, Pico Island Vineyard Culture, and Museu do Vinho. Mount Pico is 9.2 ...

                Aldeia dos Caldeirões$113

                Aldeia dos Caldeirões$113
                Hotel Caravelas

                Hotel Caravelas

                Rua Conselheiro Terra Pinheiro, 3, Madalena
                  4.0 out of 5.0
                   
                   

                  Situated on the boardwalk, this hotel is 0.7 mi (1.2 km) from Museu do Vinho and 2 mi (3.1 km) from Pico Island Vineyard Culture. Gruta das Torres and Horta ...

                  Hotel Caravelas$86

                  Hotel Caravelas$86
                  A Casa do Ouvidor

                  A Casa do Ouvidor

                  Estrada Regional, 22, Sao Roque do Pico
                    4.0 out of 5.0
                     
                     

                    This family-friendly Sao Roque do Pico villa is located near the beach, within 2 mi (3 km) of Sao Roque Church and Convent of Sao Roque do Pico. Caiado Lagoon ...

                    Adegas do Pico

                    Adegas do Pico

                    Rua do Ramal, 14, Sao Roque do Pico
                      4.0 out of 5.0
                       
                       

                      Situated by the ocean, this romantic country house is within 12 mi (20 km) of Sao Roque Church, Convent of Sao Roque do Pico, and Caiado Lagoon. Lajes Whaling ...

                      Adegas do Pico$93

                      Adegas do Pico$93