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Fifth Avenue South Vacations

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

Hotwire can help you find your travel bliss with Fifth Avenue South 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 Fifth Avenue South

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 Fifth Avenue South 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 Fifth Avenue South well.

Fifth Avenue South Flight + Hotel packages

Top Hotel Deals

See all 1,092 Properties in Fifth Avenue South
The Inn on Fifth

The Inn on Fifth

699 5th Ave S, Naples
    4.0 out of 5.0
     
     

    Set in picturesque Old Naples, this smoke-free hotel is adjacent to galleries, designer shops, and restaurants; 5 blocks from the Gulf of Mexico; and a half-mile ...

    The Inn on Fifth$169

    The Inn on Fifth$169
    Naples Bay Resort

    Naples Bay Resort

    1500 Fifth Ave S, Naples
      4.0 out of 5.0
       
       

      Located on Naples Bay, this Naples hotel is 0.5 miles (0.8 kilometers) from the Tin City Shops and within 2 miles (3.2 kilometers) of Naples Pier. Naples Municipal ...

      Naples Bay Resort$144

      Naples Bay Resort$144
      Bayfront Inn Fifth Avenue

      Bayfront Inn Fifth Avenue

      1221 5th Ave S, Naples
        3.5 out of 5.0
         
         

        Located in waterside downtown Naples on 5th Avenue, this Caribbean-inspired hotel rests on Naples Bay; an island-themed restaurant provides waterfront ...

        Bayfront Inn Fifth Avenue$94

        Bayfront Inn Fifth Avenue$94
        Hyatt House Naples/5th Avenue

        Hyatt House Naples/5th Avenue

        1345 5th Avenue South, Naples
          3.5 out of 5.0
           
           

          Situated by the ocean, this hotel is 0.1 mi (0.1 km) from Fifth Avenue South and within 3 mi (5 km) of Naples Pier and Naples Zoo at Caribbean Gardens. Tin City ...

          Hyatt House Naples/5th Avenue$119

          Hyatt House Naples/5th Avenue$119
          Club Level Suites at Inn On Fifth

          Club Level Suites at Inn On Fifth

          699B 5th avenue South, Naples
            4.5 out of 5.0
             
             

            Located in Old Naples, this luxury hotel is within 1 mi (2 km) of Fifth Avenue South and Naples Pier. Naples Zoo at Caribbean Gardens is 2.3 mi (3.6 km) ...

            Club Level Suites at Inn On Fifth$329

            Club Level Suites at Inn On Fifth$329
            The Escalante

            The Escalante

            290 5th Ave S, Naples
              3.5 out of 5.0
               
               

              Located in Old Naples, this spa hotel is within 1 mi (2 km) of Fifth Avenue South and Naples Pier. Naples Zoo at Caribbean Gardens is 2.6 mi (4.3 km) away.

              The Escalante$245

              The Escalante$245
              La Quinta Inn & Suites Naples Downtown

              La Quinta Inn & Suites Naples Downtown

              1555 5th Ave S, Naples
                2.5 out of 5.0
                 
                 

                Located in the heart of Naples, this hotel is 0.1 mi (0.1 km) from Fifth Avenue South and within 3 mi (5 km) of Naples Pier and Naples Zoo at Caribbean Gardens. ...

                5th South #105 Condo 480 by RedAwning

                5th South #105 Condo 480 by RedAwning

                480 5th St S, Naples
                  3.0 out of 5.0
                   
                   

                  Located in Old Naples, this condo building is within 1 mi (2 km) of Fifth Avenue South and Naples Pier. Naples Zoo at Caribbean Gardens is 2.4 mi (3.8 km) ...

                  5th South #201 Condo 480 by RedAwning

                  5th South #201 Condo 480 by RedAwning

                  480 5th St S, Naples
                    3.0 out of 5.0
                     
                     

                    Located in Old Naples, this condo building is within 1 mi (2 km) of Fifth Avenue South and Naples Pier. Naples Zoo at Caribbean Gardens is 2.4 mi (3.8 km) ...

                    JW Marriott Marco Island Beach Resort

                    JW Marriott Marco Island Beach Resort

                    400 S Collier Blvd, Marco Island
                      4.0 out of 5.0
                       
                       

                      With the Gulf of Mexico at its door, this 11-story white-sand beachfront resort sits on the southwest tip of the island within 20 miles of Naples and 40 miles ...

                      JW Marriott Marco Island Beach Resort$314

                      JW Marriott Marco Island Beach Resort$314

                      Top Flight Deals

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