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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).

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Upper Florida Keys Holiday Homes & Rentals (300+)

  • 1 - 50 of 300+
Additional service fee may apply.
    Wonderful! 4.8/5
    (24 reviews)
    avg/night
    • 2 BR
    • 2 BA
    • Sleeps 8
    Condo #28760vb
    24
    Viewed 33 times in the last 48 hours
      Wonderful! 4.9/5
      (27 reviews)
      avg/night
      • 2 BR
      • 2 BA
      • Sleeps 8
      Townhome #714337vb
      27
      Viewed 69 times in the last 48 hours
        Wonderful! 4.8/5
        (12 reviews)
        avg/night
        • 1 BR
        • 1 BA
        • Sleeps 4
        Condo #3998195
        12
        Viewed 52 times in the last 48 hours
          Wonderful! 4.8/5
          (33 reviews)
          avg/night
          • 2 BR
          • 2 BA
          • Separate Toilet
          • Sleeps 4
          House #513264vb
          33
          Viewed 43 times in the last 48 hours
            • 2 BR
            • 2 BA
            • Separate Toilet
            • Sleeps 6
            House #823516vb
            4
            Viewed 17 times in the last 48 hours
              Excellent! 4.7/5
              (32 reviews)
              avg/night
              • 2 BR
              • 2 BA
              • Separate Toilet
              • Sleeps 6
              Townhome #484134vb
              32
              Viewed 50 times in the last 48 hours
                Exceptional! 5.0/5
                (11 reviews)
                avg/night
                • 4 BR
                • 4 BA
                • Sleeps 10
                House #816307vb
                11
                Viewed 51 times in the last 48 hours
                  Wonderful! 4.9/5
                  (28 reviews)
                  avg/night
                  • 3 BR
                  • 3 BA
                  • Sleeps 6
                  House #452120vb
                  28
                  Viewed 24 times in the last 48 hours
                    Wonderful! 4.9/5
                    (19 reviews)
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    Condo #201329vb
                    19
                    Viewed 63 times in the last 48 hours
                      Wonderful! 4.8/5
                      (21 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 8
                      House #733623vb
                      21
                      Viewed 56 times in the last 48 hours
                        Exceptional! 5.0/5
                        (8 reviews)
                        avg/night
                        • 2 BR
                        • 2 BA
                        • Separate Toilet
                        • Sleeps 6
                        House #819589vb
                        8
                        Viewed 5 times in the last 48 hours
                          Excellent! 4.5/5
                          (21 reviews)
                          avg/night
                          • 2 BR
                          • 1 BA
                          • Sleeps 5
                          Mobile Home #678078vb
                          21
                          Viewed 48 times in the last 48 hours
                            Wonderful! 4.9/5
                            (61 reviews)
                            avg/night
                            • 2 BR
                            • 2 BA
                            • Sleeps 7
                            Condo #191399
                            61
                            Viewed 28 times in the last 48 hours
                              Excellent! 4.7/5
                              (7 reviews)
                              avg/night
                              • 4 BR
                              • 3 BA
                              • Sleeps 8
                              House #680648vb
                              7
                              Viewed 40 times in the last 48 hours
                                Wonderful! 4.8/5
                                (20 reviews)
                                avg/night
                                • 2 BR
                                • 2 BA
                                • Sleeps 6
                                Condo #301565
                                20
                                Viewed 36 times in the last 48 hours
                                  Exceptional! 5.0/5
                                  (24 reviews)
                                  avg/night
                                  • 6 BR
                                  • 5 BA
                                  • Sleeps 15
                                  House #512751vb
                                  24
                                  Viewed 45 times in the last 48 hours
                                    Excellent! 4.5/5
                                    (15 reviews)
                                    avg/night
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 10
                                    House #314828
                                    15
                                    Viewed 62 times in the last 48 hours
                                      avg/night
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 6
                                      Cottage #225990
                                      3
                                      Viewed 13 times in the last 48 hours
                                        Exceptional! 5.0/5
                                        (5 reviews)
                                        avg/night
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 6
                                        Cottage #107982
                                        5
                                        Viewed 14 times in the last 48 hours
                                          Wonderful! 4.8/5
                                          (30 reviews)
                                          avg/night
                                          • 4 BR
                                          • 4 BA
                                          • Sleeps 12
                                          House #311833
                                          30
                                          Viewed 18 times in the last 48 hours
                                            Exceptional! 5.0/5
                                            (5 reviews)
                                            avg/night
                                            • 4 BR
                                            • 3 BA
                                            • Separate Toilet
                                            • Sleeps 14
                                            Estate #755494vb
                                            5
                                            Viewed 11 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (46 reviews)
                                              avg/night
                                              • 3 BR
                                              • 3 BA
                                              • Sleeps 10
                                              Townhome #261841vb
                                              46
                                              Viewed 68 times in the last 48 hours
                                                Excellent! 4.5/5
                                                (12 reviews)
                                                avg/night
                                                • 2 BR
                                                • 1 BA
                                                • Separate Toilet
                                                • Sleeps 6
                                                Condo #49455vb
                                                12
                                                Viewed 28 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (16 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 5
                                                  Condo #423610vb
                                                  16
                                                  Viewed 22 times in the last 48 hours
                                                    Wonderful! 4.8/5
                                                    (17 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 1 BA
                                                    • Separate Toilet
                                                    • Sleeps 6
                                                    Townhome #479565vb
                                                    17
                                                    Viewed 36 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (16 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 2 BA
                                                      • Separate Toilet
                                                      • Sleeps 6
                                                      House #640459vb
                                                      16
                                                      Viewed 29 times in the last 48 hours
                                                        Excellent! 4.7/5
                                                        (21 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        Apartment #17772
                                                        21
                                                        Viewed 20 times in the last 48 hours
                                                          Excellent! 4.7/5
                                                          (23 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          Condo #732772vb
                                                          23
                                                          Viewed 7 times in the last 48 hours
                                                            avg/night
                                                            • 2 BR
                                                            • 1 BA
                                                            • Separate Toilet
                                                            • Sleeps 6
                                                            Condo #1901373
                                                            4
                                                            Viewed 7 times in the last 48 hours
                                                              Exceptional! 5.0/5
                                                              (5 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Condo #800518vb
                                                              5
                                                              Viewed 6 times in the last 48 hours
                                                                • 5 BR
                                                                • 4 BA
                                                                • Sleeps 10
                                                                House #356424vb
                                                                1
                                                                  Wonderful! 4.9/5
                                                                  (27 reviews)
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 10
                                                                  House #123633vb
                                                                  27
                                                                  Viewed 17 times in the last 48 hours
                                                                    • 10 BR
                                                                    • 8 BA
                                                                    • Sleeps 20
                                                                    Estate #728291vb
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      Condo #440087vb
                                                                      1
                                                                      Viewed 475 times in the last 48 hours
                                                                        Excellent! 4.7/5
                                                                        (26 reviews)
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        Apartment #372663vb
                                                                        26
                                                                        Viewed 55 times in the last 48 hours
                                                                          Exceptional! 5.0/5
                                                                          (23 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 4
                                                                          House #554505vb
                                                                          23
                                                                          Viewed 29 times in the last 48 hours
                                                                            Exceptional! 5.0/5
                                                                            (48 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 3 BA
                                                                            • Sleeps 6
                                                                            Villa #338691
                                                                            48
                                                                            Viewed 27 times in the last 48 hours
                                                                              Excellent! 4.4/5
                                                                              (29 reviews)
                                                                              avg/night
                                                                              • 1 BR
                                                                              • 2 BA
                                                                              • Sleeps 5
                                                                              Condo #395120vb
                                                                              29
                                                                              Viewed 42 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (23 reviews)
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • Sleeps 8
                                                                                Townhome #778346vb
                                                                                23
                                                                                Viewed 24 times in the last 48 hours
                                                                                  Exceptional! 5.0/5
                                                                                  (8 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Separate Toilet
                                                                                  • Sleeps 6
                                                                                  Condo #312619vb
                                                                                  8
                                                                                  Viewed 5 times in the last 48 hours
                                                                                    Excellent! 4.6/5
                                                                                    (50 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    Condo #175223
                                                                                    50
                                                                                    Viewed 28 times in the last 48 hours
                                                                                      Excellent! 4.7/5
                                                                                      (48 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Separate Toilet
                                                                                      • Sleeps 4
                                                                                      Townhome #314711
                                                                                      48
                                                                                      Viewed 24 times in the last 48 hours
                                                                                        Exceptional! 5.0/5
                                                                                        (58 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        Condo #400639vb
                                                                                        58
                                                                                        Viewed 6 times in the last 48 hours
                                                                                          Exceptional! 5.0/5
                                                                                          (30 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          Townhome #580000vb
                                                                                          30
                                                                                          Viewed 8 times in the last 48 hours
                                                                                            Wonderful! 4.8/5
                                                                                            (12 reviews)
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 3 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 8
                                                                                            House #553460vb
                                                                                            12
                                                                                            Viewed 28 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (5 reviews)
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 8
                                                                                              House #4222484
                                                                                              5
                                                                                              Viewed 37 times in the last 48 hours
                                                                                                Wonderful! 4.8/5
                                                                                                (37 reviews)
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 4 BA
                                                                                                • Sleeps 14
                                                                                                House #406052vb
                                                                                                37
                                                                                                Viewed 34 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (60 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                  Condo #2218vb
                                                                                                  60
                                                                                                  Viewed 6 times in the last 48 hours
                                                                                                    Exceptional! 5.0/5
                                                                                                    (12 reviews)
                                                                                                    avg/night
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Separate Toilet
                                                                                                    • Sleeps 6
                                                                                                    Condo #750103vb
                                                                                                    12
                                                                                                    Viewed 55 times in the last 48 hours
                                                                                                      Wonderful! 4.8/5
                                                                                                      (75 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      Condo #311664
                                                                                                      75
                                                                                                      Viewed 9 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      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