HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar

Make a holiday rental property or villa to rent in the Upper Florida Keys your home away from home

Upper Florida Keys holidays are a hive of activity, where blazing sunshine, refreshing tropical breezes and the gleaming colours of white sand, lush vegetation and azure skies for the backdrop of every photograph. The Upper Florida Keys are known worldwide for their deep sea fishing and scuba diving credentials, but there is far more to discover from an Upper Florida Keys villa for rent, from the amazing wildlife to the lively bars and restaurants. Whatever you end up doing on your Florida Keys holiday, you cannot fail to completely unwind, relax and return home with a new zest for life.

Things to do on holiday in the Upper Florida Keys

The snorkelling and scuba diving from an Upper Florida Keys villa for rent are absolutely sensational. There are a good number of underwater national parks, including the Pennekamo State Park, which protects the only living barrier reef in the USA, with divers flocking from around the world to discover its watery treasures. The Key Largo Undersea Park is also a wonderful place to snorkel and dive, and the USS Spiegel Grove Shipwreck is one of the finest wreck dives you can do.

The Upper Florida Keys deep sea fishing is hugely popular with both visitors and locals alike. The warm waters which surround the Keys are perfect for many species of game fish, and vast tarpon, marlin and tuna are often returned to shore with the glee of the fisherman clear for all to see!

On land, there are plenty of places to relax. The stunning white sand beaches would be the main attraction of most resorts around the world, such are the attractions of the Upper Florida Keys, they only get a brief mention in most guides! However, you can spend many days stretched out on the powder soft white sands of the Florida Keys, just letting the world drift by in glorious silence. There are also a great range of lively bars and atmospheric restaurants in which to get some refreshment, Florida style.

Places to stay on holiday in the Upper Florida Keys

The village of Islamorada still maintains its wonderfully laid back atmosphere, providing a perfect escape from the break-neck pace of life you leave behind. You cannot help but to relax from a Florida Keys villa for rent in Islamorada, and if you are hoping to go deep sea fishing in the Florida Keys or simply sail in the warm waters of the Gulf, you cannot beat a villa for rent in Islamorada. Huge sailfish, marlin and tuna are regularly caught off the shores here, and chartered fishing trips are readily available for visitors,

Key Largo is the northernmost of the Florida Keys islands. The interior of the island is a remarkable mix of tropical hardwood forests, sleepy creeks and stunning corals. Key Largo is one of the finest scuba diving destinations in America, sandwiched between the Everglades National Park to the west and America’s only living coral reef to the east. Diving the wreck of the Spiegel Grove is an absolutely unforgettable experience, but if you wish to stay above the surface of the seas, there are some sensational places to kayak, and the Florida Keys deep sea fishing from here is remarkably good.

Weather in the Upper Florida Keys

The climate of the Florida Keys is quite exceptional. Average monthly temperatures remain between 22°C and 32°C throughout the year, with January, whilst being the coldest month, still offering a stunning climate from which to escape the British winter.

Travel to the Upper Florida Keys

The closest international airport receiving direct flights from the UK is Miami International (MIA).Virgin Atlantic and British Airways both provide a range of flights to Miami, and from there you can either drive or get a short hop flight to Key West (NQX).

Cancel Clear Filters Apply Filters

Property Type

Popular Searches

Payment Options

Facilities

Managed By

Local Area

Property Details

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!
  • 1 - 50 of 1,170
    • 2 BR
    • 2 BA
    • Sleeps 8
    25
      • 1 BR
      • 1 BA
      • Sleeps 4
      10
        • 2 BR
        • 2 BA
        • Sleeps 6
        24
          • 2 BR
          • 2 BA
          • Separate Toilet
          • Sleeps 6
          41
            • 2 BR
            • 2 BA
            • Separate Toilet
            • Sleeps 4
            30
              • 2 BR
              • 2 BA
              • Separate Toilet
              • Sleeps 6
              36
                • 2 BR
                • 2 BA
                • Separate Toilet
                • Sleeps 6
                31
                  • 2 BR
                  • 2 BA
                  • Sleeps 6
                  64
                    • 4 BR
                    • 4 BA
                    • Sleeps 10
                    9
                      • 2 BR
                      • 2 BA
                      • Separate Toilet
                      • Sleeps 6
                      4
                        • 3 BR
                        • 2 BA
                        • Sleeps 7
                        19
                          • 5 BR
                          • 5 BA
                          • Separate Toilets
                          • Sleeps 12
                          20
                            • 3 BR
                            • 3 BA
                            • Sleeps 6
                            28
                              • 2 BR
                              • 2 BA
                              • Sleeps 7
                              95
                                • 3 BR
                                • 2 BA
                                • Sleeps 8
                                20
                                  • 2 BR
                                  • 2 BA
                                  • Separate Toilet
                                  • Sleeps 6
                                  8
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 5
                                    21
                                      • 4 BR
                                      • 2 BA
                                      • Separate Toilet
                                      • Sleeps 15
                                      25
                                        • 4 BR
                                        • 3 BA
                                        • Sleeps 8
                                        5
                                          • 6 BR
                                          • 5 BA
                                          • Sleeps 15
                                          23
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 10
                                            15
                                              • 3 BR
                                              • 2 BA
                                              • Separate Toilet
                                              • Sleeps 6
                                              5
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 6
                                                3
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  5
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    6
                                                      • 5 BR
                                                      • 4 BA
                                                      • Separate Toilet
                                                      • Sleeps 10
                                                      1 Review
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        35
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          20
                                                            • 2 BR
                                                            • 1 BA
                                                            • Separate Toilet
                                                            • Sleeps 6
                                                            4
                                                              • 4 BR
                                                              • 4 BA
                                                              • Sleeps 12
                                                              29
                                                                • 4 BR
                                                                • 3 BA
                                                                • Separate Toilet
                                                                • Sleeps 14
                                                                5
                                                                  • 4 BR
                                                                  • 3 BA
                                                                  • Sleeps 8
                                                                  15
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    24
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Separate Toilet
                                                                      • Sleeps 6
                                                                      10
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        22
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          21
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                            5
                                                                              • 3 BR
                                                                              • 3 BA
                                                                              • Sleeps 7
                                                                              2 Reviews
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 8
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Separate Toilet
                                                                                  • Sleeps 6
                                                                                  4
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    1 Review
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Separate Toilet
                                                                                      • Sleeps 6
                                                                                      7
                                                                                        • 5 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 10
                                                                                        1 Review
                                                                                          • 10 BR
                                                                                          • 8 BA
                                                                                          • Sleeps 20
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 10
                                                                                            27
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              28
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Separate Toilet
                                                                                                • Sleeps 6
                                                                                                8
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  21
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Separate Toilet
                                                                                                    • Sleeps 6
                                                                                                    15
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 5
                                                                                                      16
                                                                                                      • 1 - 50 of 1,170
                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      Beautiful place to stay.

                                                                                                      5 of 5
                                                                                                      We really loved to stay here. Jorge was very attentive. We met him when we arrived and when we left. The property is well kept, kitchen well equipped, mattresses very comfortable. We had everything we needed to feel at home. We loved the view at the lagoon, the iguanas crossing our way every day, the two pools....everything. We highly recommend Jorge's place.
                                                                                                      • Review Submitted: 14-Aug-2016
                                                                                                      • Date of Stay: Aug 2016

                                                                                                      What a fantastic place to stay!

                                                                                                      5 of 5
                                                                                                      This condo has it all! It's one of the best situated in the Upper Keys area and the views from the balcony of the Gulf AND Atlantic Ocean were fantastic. It has all the comforts of home, is beautifully furnished with keysy colours. The whole apartment is very clean, light and refreshing. The grounds are nicely maintained and include a beautiful swimming pool that is larger than most and 2 tennis courts. Just a real nice place to be for relaxation, swimming in the pool, fishing in the Marina and snorkelling from the beach area. Lots of fine dining close by, cooked on the gas BBQ on the balcony a few nights! Brill!!. My wife and I totally enjoyed our stay at Susan and Richards condo. Decided to rent a boat for a few days and even had a dock provided for us by Susan. The owners could not have been more accommodating and genuinely friendly. No more small hotel rooms for us! we saved a lot of money and had every conceivable amenity (even an electric kettle!!) We highly recommend this apartment and are already planning our next trip there! Can't wait!!
                                                                                                      • Review Submitted: 09-Sep-2008
                                                                                                      • Date of Stay: Aug 2008