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Fleming Island Vacations

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

Hotwire can help you find your travel bliss with Fleming 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 Fleming 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 Fleming 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 Fleming Island well.

Fleming Island Flight + Hotel packages

Top Hotel Deals

See all 145 Hotels in Fleming Island
Holiday Inn Express & Suites Fleming Island

Holiday Inn Express & Suites Fleming Island

1815 East West Pkwy., Fleming Island
    2.5 out of 5.0
     
     

    Located in the heart of Fleming Island, this hotel is 2.6 mi (4.2 km) from The Golf Club At Fleming Island and within 9 mi (15 km) of Jacksonville Naval Air ...

    Holiday Inn Express & Suites Fleming Island$110

    Holiday Inn Express & Suites Fleming Island$110
    Omni Jacksonville Hotel

    Omni Jacksonville Hotel

    245 Water St, Jacksonville
      4.0 out of 5.0
       
       

      The Omni Jacksonville Hotel is downtown, in the cultural and business districts. The hotel is opposite the Times-Union Center for the Performing Arts, one block ...

      Omni Jacksonville Hotel$119

      Omni Jacksonville Hotel$119
      Hyatt Regency Jacksonville

      Hyatt Regency Jacksonville

      225 E Coastline Dr, Jacksonville
        4.0 out of 5.0
         
         

        This downtown riverfront hotel is in the city's business and retail district next to Jacksonville shopping, dining, and entertainment venues.

        Hyatt Regency Jacksonville$109

        Hyatt Regency Jacksonville$109
        Best Western Southside Hotel & Suites

        Best Western Southside Hotel & Suites

        4580 Collins Rd, Orange Park
          2.5 out of 5.0
           
           

          Situated in the business district, this hotel is 1.2 mi (1.9 km) from bestbet Orange Park and 2.4 mi (3.8 km) from Jacksonville Naval Air Station. Westside Regional ...

          Best Western Southside Hotel & Suites$71

          Best Western Southside Hotel & Suites$71
          Lexington Hotel & Conference Center - Jacksonville Riverwalk

          Lexington Hotel & Conference Center - Jacksonville Riverwalk

          1515 Prudential Dr, Jacksonville
            3.5 out of 5.0
             
             

            The Lexington Hotel & Conference Center – Jacksonville Riverwalk is located across from Jacksonville Landing, on the south bank of the river, 1 mile (1.6 kilometers) ...

            Lexington Hotel & Conference Center - Jacksonville Riverwalk$83

            Lexington Hotel & Conference Center - Jacksonville Riverwalk$83
            Baymont by Wyndham Jacksonville/Butler Blvd

            Baymont by Wyndham Jacksonville/Butler Blvd

            7030 Bonneval Road, Jacksonville
              2.5 out of 5.0
               
               

              Located in Southpoint, this hotel is within 6 mi (10 km) of Dog Wood Park of Jacksonville, St. Johns Town Center, and The Avenues. Crabtree Park and Hands on ...

              Baymont by Wyndham Jacksonville/Butler Blvd$72

              Baymont by Wyndham Jacksonville/Butler Blvd$72
              Country Inn & Suites by Radisson, Jacksonville, FL

              Country Inn & Suites by Radisson, Jacksonville, FL

              5945 Youngerman Cir E, Jacksonville
                3.0 out of 5.0
                 
                 

                Situated in Jacksonville, this hotel is 1.3 mi (2 km) from Orange Park Mall and 2.8 mi (4.6 km) from Orange Park Medical Center. Jacksonville Naval Air Station ...

                Country Inn & Suites by Radisson, Jacksonville, FL$87

                Country Inn & Suites by Radisson, Jacksonville, FL$87
                Stars Rest Inn

                Stars Rest Inn

                510 Lane Avenue S, Jacksonville
                  2.0 out of 5.0
                   
                   

                  Located in Jacksonville, this family-friendly motel is 2.8 mi (4.5 km) from Hyde Park Golf Club, and within 6 mi (10 km) of Sally Corporation and Cummer Museum ...

                  Stars Rest Inn$45

                  Stars Rest Inn$45
                  Ramada Hotel & Conf Cntr by Wyndham Jacksonville/Baymeadows

                  Ramada Hotel & Conf Cntr by Wyndham Jacksonville/Baymeadows

                  9150 Baymeadows Road, Jacksonville
                    3.0 out of 5.0
                     
                     

                    Situated in Jacksonville, this hotel is within 6 mi (10 km) of Dog Wood Park of Jacksonville, The Avenues, and St. Johns Town Center. University of North Florida ...

                    Ramada Hotel & Conf Cntr by Wyndham Jacksonville/Baymeadows$79

                    Ramada Hotel & Conf Cntr by Wyndham Jacksonville/Baymeadows$79
                    Extended Stay America - Jacksonville - Deerwood Park

                    Extended Stay America - Jacksonville - Deerwood Park

                    8801 Perimeter Park Blvd, Jacksonville
                      2.5 out of 5.0
                       
                       

                      Located in Southpoint-Butler Blvd, this hotel is 2.5 mi (4 km) from St. Johns Town Center and 2.9 mi (4.7 km) from Hands on Children's Museum. University of ...

                      Extended Stay America - Jacksonville - Deerwood Park$66

                      Extended Stay America - Jacksonville - Deerwood Park$66

                      Top Flight Deals

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