Villas in Key West and Holiday rentals - Holiday Lettings - Holiday Rentals Key West

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474 Holiday homes

(2) Very Good 

    19

    Yacht rental in Key West

    Florida Keys / Key West

    2 6 2 nights min

    • 2 bedrooms
    • sleeps 6
    • 2 nights min
    • Swimming pool
    • Child friendly
    • Car not necessary

    from £176 / night

    £1,232 / week

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    Responds fast!
    avg. 1 hour 3 minutes

    from £176 / night

    (6) Excellent 

      70

      Holiday yacht in Key West

      Florida Keys / Key West

      3 6 1 night min

      • 3 bedrooms
      • sleeps 6
      • 1 night min
      • Child friendly
      • Air conditioning

      from £1,892 / night

      £11,394 - £13,858 / week

      Book View

      from £1,892 / night

      (33) Excellent 

        28

        Key West holiday houseboat rental

        Florida Keys / Key West

        4 10 2 nights min

        • 4 bedrooms
        • sleeps 10
        • 2 nights min
        • Swimming pool
        • Child friendly
        • Car not necessary

        from £352 / night

        £2,464 / week

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        Responds fast!
        avg. 1 hour 3 minutes

        from £352 / night

          19

          Home rental in Key West

          Florida Keys / Key West

          1 2 6 nights min

          • 1 bedroom
          • sleeps 2
          • 6 nights min
          • Swimming pool
          • Child friendly
          • Car not necessary

          from £185 / night

          £1,294 / week

          Book View

          from £185 / night

          (52) Very Good 

          Certificate of Excellence

            17

            Key West holiday apartment let

            Florida Keys / Key West

            2 5 min stay varies

            • 2 bedrooms
            • sleeps 5
            • min stay varies
            • Beach / lakeside relaxation
            • Swimming pool
            • Car not necessary
            “Perfect!” This was the perfect size suite for 4 adults, with a little pool oasis right off our doorstep, in the center of it all without the noise of Duval. Loved every second of my stay!

            Certificate of Excellence

            from £228 / night

            £1,596 / week

            Book View

            from £228 / night

            (69) Very Good 

            Certificate of Excellence

              11

              Apartment rental in Key West

              Florida Keys / Key West

              3 8 min stay varies

              • 3 bedrooms
              • sleeps 8
              • min stay varies
              • Beach / lakeside relaxation
              • Swimming pool
              • Car not necessary

              Certificate of Excellence

              from £290 / night

              £2,027 / week

              Book View

              from £290 / night

              (1) Excellent 

                19

                Key West holiday townhouse rental

                Florida Keys / Key West

                2 6 min stay varies

                • 2 bedrooms
                • sleeps 6
                • min stay varies
                • Swimming pool
                • Child friendly
                • Air conditioning

                from £351 / night

                £2,458 / week

                Book View

                from £351 / night

                (35) Excellent 

                Certificate of Excellence

                  14

                  Holiday apartment in Key West

                  Florida Keys / Key West

                  2 6 min stay varies

                  • 2 bedrooms
                  • sleeps 6
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Swimming pool
                  • Car not necessary
                  “Awesome - you wont be disappointed!” Great location; block from Duval St. but far enough to not be affected by the crow. Market grocer very near by. Suite had everything you could need, and was in excellent condition! The rent, pre-communication, key-less arrival, and overall process was very efficient. We couldn't be happier!

                  Certificate of Excellence

                  from £219 / night

                  £1,534 / week

                  Book View

                  from £219 / night

                  (38) Excellent 

                  Certificate of Excellence

                    17

                    Holiday apartment in Key West

                    Florida Keys / Key West

                    2 6 min stay varies

                    • 2 bedrooms
                    • sleeps 6
                    • min stay varies
                    • Swimming pool
                    • Car not necessary
                    • Air conditioning

                    Certificate of Excellence

                    from £245 / night

                    £1,715 / week

                    Book View

                    from £245 / night

                    (40) Excellent 

                      38

                      Holiday apartment rental

                      Florida Keys / Key West

                      2 6 min stay varies

                      • 2 bedrooms
                      • sleeps 6
                      • min stay varies
                      • Beach / lakeside relaxation
                      • Nearest beach 0.2 km
                      • Swimming pool
                      “Tropical Paradise” The place was absolutely beautiful, first class accomodations. It was as nice as any island in the Carribbean with the comfort and safety of being in the United States and a whole lot closer. Hope to go back again soon.

                      from £308 / night

                      £1,940 / week

                      Book View

                      Responds fast!
                      avg. 1 hour 57 minutes

                      from £308 / night

                      (3) Average 

                        24

                        Home rental in Key West

                        Florida Keys / Key West

                        3 8 min stay varies

                        • 3 bedrooms
                        • sleeps 8
                        • min stay varies
                        • Child friendly
                        • Air conditioning
                        • Private garden

                        from £599 / night

                        £4,188 / week

                        Book View

                        from £599 / night

                        (1) Excellent 

                          16

                          Holiday apartment in Key West

                          Florida Keys / Key West

                          1 2 30 nights min

                          • 1 bedroom
                          • sleeps 2
                          • 30 nights min
                          • Beach / lakeside relaxation
                          • Nearest beach 0.5 km
                          • Car not necessary

                          from £176 / night

                          £1,232 / week

                          Book View

                          from £176 / night

                          (85) Very Good 

                            26

                            Apartment rental in Key West with swimming pool

                            Florida Keys / Key West

                            2 5 3 nights min

                            • 2 bedrooms
                            • sleeps 5
                            • 3 nights min
                            • Swimming pool
                            • Child friendly
                            • Air conditioning
                            “A fun get away” Just back from a short stay in Key West with my daughters .. Really enjoyed staying here .. the condo was very clean and roomy .. and quiet .. unfortunately never made it into the pool as it closed at 8 pm and our site seeing keep us out past that time .. wished the hrs were a bit more later, like 10pm .. but we spent out time in the beautiful waters of the keys .. do not go to smathers beach, very yucky water .. about a 10-15 minute drive into town, hope to have a bit more time next time, would have liked to rent some bikes and make the ride .. the receptionist that checked us in gave us bad info that sent us walking half way around the island looking for a chili's restaurant that never existed .. but found roosters ..iguanas .. baby chicks .. and manatees on our travels .. was a nice 3 day break .. hope to go back sooner than 20 yrs

                            from £194 / night

                            £1,320 - £1,998 / week

                            Book View

                            from £194 / night

                            (4) Excellent 

                              48

                              Holiday condo in Key West

                              Florida Keys / Key West

                              2 6 3 nights min

                              • 2 bedrooms
                              • sleeps 6
                              • 3 nights min
                              • Beach / lakeside relaxation
                              • Swimming pool
                              • Child friendly

                              from £264 / night

                              £1,817 - £2,341 / week

                              Book View

                              Responds fast!
                              avg. 2 hours 11 minutes

                              from £264 / night

                              (7) Excellent 

                                15

                                Apartment rental in Key West

                                Florida Keys / Key West

                                2 4 7 nights min

                                • 2 bedrooms
                                • sleeps 4
                                • 7 nights min
                                • Beach / lakeside relaxation
                                • Swimming pool
                                • Child friendly

                                from £256 / night

                                £1,914 / week

                                Book View

                                from £256 / night

                                  14

                                  Key West holiday home rental

                                  Florida Keys / Key West

                                  2 6 30 nights min

                                  • 2 bedrooms
                                  • sleeps 6
                                  • 30 nights min
                                  • Child friendly
                                  • Air conditioning
                                  • Pet friendly

                                  from £369 / night

                                  £2,581 / week

                                  Book View

                                  from £369 / night

                                  (4) Excellent 

                                    22

                                    Holiday condo in Key West

                                    Florida Keys / Key West

                                    2 6 5 nights min

                                    • 2 bedrooms
                                    • sleeps 6
                                    • 5 nights min
                                    • Beach / lakeside relaxation
                                    • Swimming pool
                                    • Child friendly

                                    from £308 / night

                                    £1,760 / week

                                    Book View

                                    from £308 / night

                                      13

                                      Holiday home rental

                                      Florida Keys / Key West

                                      2 4 28 nights min

                                      • 2 bedrooms
                                      • sleeps 4
                                      • 28 nights min
                                      • Nearest beach 2 km
                                      • Child friendly
                                      • Air conditioning

                                      from £106 / night

                                      £739 / week

                                      Book View

                                      from £106 / night

                                      (3) Very Good 

                                        17

                                        Key West holiday apartment rental

                                        Florida Keys / Key West

                                        2 4 1 night min

                                        • 2 bedrooms
                                        • sleeps 4
                                        • 1 night min
                                        • Beach / lakeside relaxation
                                        • Child friendly
                                        • Air conditioning

                                        from £146 / night

                                        £1,017 / week

                                        Book View

                                        Responds fast!
                                        avg. 3 hours 24 minutes

                                        from £146 / night

                                        (2) Excellent 

                                          51

                                          Holiday yacht in Key West

                                          Florida Keys / Key West

                                          4 6 2 nights min

                                          • 4 bedrooms
                                          • sleeps 6
                                          • 2 nights min
                                          • Nearest beach 1 km
                                          • Swimming pool
                                          • Air conditioning

                                          from £219 / night

                                          £1,534 / week

                                          Book View

                                          from £219 / night

                                            19

                                            Key West holiday condo rental

                                            Florida Keys / Key West

                                            2 4 7 nights min

                                            • 2 bedrooms
                                            • sleeps 4
                                            • 7 nights min
                                            • Nearest beach 0.5 km
                                            • Swimming pool
                                            • Child friendly

                                            from £271 / night

                                            £1,891 / week

                                            Book View

                                            Responds fast!
                                            avg. 3 hours 43 minutes

                                            from £271 / night

                                            (2) Excellent 

                                              24

                                              Holiday home rental

                                              Florida Keys / Key West

                                              1 2 min stay varies

                                              • 1 bedroom
                                              • sleeps 2
                                              • min stay varies
                                              • Child friendly

                                              from £142 / night

                                              £990 / week

                                              Enquire View

                                              from £142 / night

                                              (1) Average 

                                                23

                                                Holiday apartment with shared pool in Key West

                                                Florida Keys / Key West

                                                2 5 7 nights min

                                                • 2 bedrooms
                                                • sleeps 5
                                                • 7 nights min
                                                • Swimming pool
                                                • Child friendly

                                                from £139 / night

                                                £969 / week

                                                Enquire View

                                                from £139 / night

                                                (1) Excellent 

                                                  24

                                                  Holiday home with swimming pool in Key West

                                                  Florida Keys / Key West

                                                  2 4 7 nights min

                                                  • 2 bedrooms
                                                  • sleeps 4
                                                  • 7 nights min
                                                  • Swimming pool
                                                  • Child friendly

                                                  from £150 / night

                                                  £1,049 / week

                                                  Enquire View

                                                  from £150 / night

                                                  (27) Very Good 

                                                    24

                                                    Holiday home with shared pool in Key West

                                                    Florida Keys / Key West

                                                    2 6 7 nights min

                                                    • 2 bedrooms
                                                    • sleeps 6
                                                    • 7 nights min
                                                    • Swimming pool
                                                    • Child friendly
                                                    “Beautiful House, sometimes loud” We stayed at the artist's Garden for one week. There were 4 adults and an 11 month old. The house is gorgeous, lots of interesting art. Some of it we had to move out of reach of our 11 month old, but that was easy enough. The only downside to this house is that it's located across the street from the post office. It wouldn't be bad except the bedroom windows face the post office. Some mornings the postal trucks banged around starting at 4:52 am! I finally had to put on a white noise app every night to drown them and the roosters out. (The roosters is a Key West issue, not this houses's ;-) ) .. It was in a great location, easy to access all the restaurants, Duval Street and Mallory square. The pool is very close and well maintained. We definitely would consider staying here again, but if a different house in Truman annex were available not close to the post office, we'd probably choose that first. We would definitely go through at Home in Key West, though! They were wonderful and helpful. They also recommended using The Hip Tourist for renting baby equipment and it was perfect!!!

                                                    from £219 / night

                                                    £1,533 / week

                                                    Enquire View

                                                    from £219 / night

                                                      24

                                                      Holiday apartment with shared pool in Key West

                                                      Florida Keys / Key West

                                                      2 5 7 nights min

                                                      • 2 bedrooms
                                                      • sleeps 5
                                                      • 7 nights min
                                                      • Swimming pool
                                                      • Child friendly

                                                      from £150 / night

                                                      £1,049 / week

                                                      Enquire View

                                                      from £150 / night

                                                        24

                                                        Apartment rental in Key West with shared pool

                                                        Florida Keys / Key West

                                                        2 4 min stay varies

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • min stay varies
                                                        • Swimming pool
                                                        • Child friendly
                                                        • Pet friendly

                                                        from £135 / night

                                                        £942 / week

                                                        Enquire View

                                                        from £135 / night

                                                        (1) Excellent 

                                                          24

                                                          Boathouse rental in Key West

                                                          Florida Keys / Key West

                                                          2 6 min stay varies

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Nearest beach 6 km
                                                          • Swimming pool
                                                          • Child friendly

                                                          from £175 / night

                                                          £1,223 - £1,320 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 2 hours 45 minutes

                                                          from £175 / night

                                                          (12) Excellent 

                                                            17

                                                            Holiday apartment in Key West

                                                            Florida Keys / Key West

                                                            2 6 5 nights min

                                                            • 2 bedrooms
                                                            • sleeps 6
                                                            • 5 nights min
                                                            • Beach / lakeside relaxation
                                                            • Nearest beach 0 km
                                                            • Swimming pool

                                                            from £246 / night

                                                            £1,716 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 1 hour 32 minutes

                                                            from £246 / night

                                                              25

                                                              Holiday apartment with shared pool in Key West

                                                              Florida Keys / Key West

                                                              1 2 min stay varies

                                                              • 1 bedroom
                                                              • sleeps 2
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Ask owner if suitable for children
                                                              • Ask about pets

                                                              from £123 / night

                                                              £856 / week

                                                              Enquire View

                                                              from £123 / night

                                                              (1) Excellent 

                                                                23

                                                                Key West holiday home accommodation

                                                                Florida Keys / Key West

                                                                2 6 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 6
                                                                • min stay varies
                                                                • Swimming pool
                                                                • Child friendly

                                                                from £220 / night

                                                                £1,539 / week

                                                                Enquire View

                                                                from £220 / night

                                                                (3) Average 

                                                                  0

                                                                  Holiday home with shared pool in Key West

                                                                  Florida Keys / Key West

                                                                  3 6 min stay varies

                                                                  • 3 bedrooms
                                                                  • sleeps 6
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child friendly
                                                                  • Car not necessary

                                                                  from £211 / night

                                                                  £1,472 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 1 hour 51 minutes

                                                                  from £211 / night

                                                                    6

                                                                    Holiday apartment in Key West

                                                                    Florida Keys / Key West

                                                                    1 4 7 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 4
                                                                    • 7 nights min
                                                                    • Beach / lakeside relaxation
                                                                    • Swimming pool
                                                                    • Child friendly

                                                                    from £202 / night

                                                                    £1,408 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 3 hours 11 minutes

                                                                    from £202 / night

                                                                    (1) Excellent 

                                                                      58

                                                                      Holiday home with shared pool in Key West

                                                                      Florida Keys / Key West

                                                                      2 5 7 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 5
                                                                      • 7 nights min
                                                                      • Swimming pool
                                                                      • Child friendly
                                                                      • Car not necessary

                                                                      from £164 / night

                                                                      £1,146 / week

                                                                      Book View

                                                                      from £164 / night

                                                                      (5) Excellent 

                                                                        24

                                                                        Holiday home with swimming pool in Key West

                                                                        Florida Keys / Key West

                                                                        5 12 min stay varies

                                                                        • 5 bedrooms
                                                                        • sleeps 12
                                                                        • min stay varies
                                                                        • Swimming pool
                                                                        • Child friendly
                                                                        • Air conditioning

                                                                        from £538 / night

                                                                        £3,766 / week

                                                                        Enquire View

                                                                        from £538 / night

                                                                          24

                                                                          Key West holiday home rental

                                                                          Florida Keys / Key West

                                                                          3 6 min stay varies

                                                                          • 3 bedrooms
                                                                          • sleeps 6
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child friendly
                                                                          • Pet friendly

                                                                          from £215 / night

                                                                          £1,501 / week

                                                                          Enquire View

                                                                          from £215 / night

                                                                          (32) Very Good 

                                                                            24

                                                                            Key West holiday home rental

                                                                            Florida Keys / Key West

                                                                            2 6 7 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 6
                                                                            • 7 nights min
                                                                            • Swimming pool
                                                                            • Child friendly
                                                                            “Perfect Location!!!” This condo was clean comfortable and located minutes from all the action on Duval and in Mallory Square. The location was perfect combination of peace and quiet at home while only block away from all the excitement of the surrounding area. Was a little disappointed with the size of the pool on admirals lane but other than that it was a wonderful trip and would stay in the same location again. People at at Home Key West were very efficient and congenial. Thank You!!

                                                                            from £193 / night

                                                                            £1,345 / week

                                                                            Enquire View

                                                                            from £193 / night

                                                                              24

                                                                              Home letting in Key West

                                                                              Florida Keys / Key West

                                                                              2 4 min stay varies

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • min stay varies
                                                                              • Child friendly
                                                                              • Pet friendly

                                                                              from £157 / night

                                                                              £1,098 / week

                                                                              Enquire View

                                                                              from £157 / night

                                                                                9

                                                                                Holiday townhouse in Key West

                                                                                Florida Keys / Key West

                                                                                2 6 7 nights min

                                                                                • 2 bedrooms
                                                                                • sleeps 6
                                                                                • 7 nights min
                                                                                • Beach / lakeside relaxation
                                                                                • Child friendly

                                                                                from £189 / night

                                                                                £1,320 / week

                                                                                Book View

                                                                                from £189 / night

                                                                                  13

                                                                                  Holiday home in Key West

                                                                                  Florida Keys / Key West

                                                                                  2 4 30 nights min

                                                                                  • 2 bedrooms
                                                                                  • sleeps 4
                                                                                  • 30 nights min
                                                                                  • Child friendly

                                                                                  from £261 / night

                                                                                  £1,823 / week

                                                                                  Book View

                                                                                  from £261 / night

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