Verified Review icon 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 svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled
Cancel Clear Filters Apply Filters
More Filters

Price Per Night

$ $

Bedrooms

Bathrooms

Booking Options

Booking Options

Location Type

Features

Managed By

Clear Filters
Use filters to narrow your search results!
Favorite
    Viewed 10 times in the last 48 hours
    Exceptional! 5/5
    (8 reviews)
    $83
    avg/night
    (28 nights min)
    #724831
    8
    Favorite
      Viewed 9 times in the last 48 hours
      $89
      avg/night
      (30 nights min)
      #1030281
      3
      Favorite
        Viewed 23 times in the last 48 hours
        Wonderful! 4.9/5
        (18 reviews)
        svg-lightning
        avg/night
        (7 nights min)
        #34491
        18
        Favorite
          Viewed 45 times in the last 48 hours
          avg/night
          (5 nights min)
          #1021237
          4
          Favorite
            Viewed 7 times in the last 48 hours
            Exceptional! 5/5
            (33 reviews)
            avg/night
            (7 nights min)
            #429859
            33
            Favorite
              Premier Partner
              avg/night
              (7 nights min)
              #1174114
              Favorite
                Viewed 5 times in the last 48 hours
                avg/night
                (28 nights min)
                #1100727
                Favorite
                  Viewed 8 times in the last 48 hours
                  Excellent! 4.7/5
                  (11 reviews)
                  svg-lightning
                  avg/night
                  (7 nights min)
                  #36559
                  11
                  Favorite
                    Viewed 16 times in the last 48 hours
                    Excellent! 4.6/5
                    (17 reviews)
                    avg/night
                    (7 - 28 nights min)
                    #36742
                    17
                    Favorite
                      Viewed 19 times in the last 48 hours
                      avg/night
                      (5 nights min)
                      #1021238
                      3
                      Favorite
                        Viewed 5 times in the last 48 hours
                        avg/night
                        (29 nights min)
                        #991306
                        Favorite
                          Viewed 11 times in the last 48 hours
                          View details for price
                          (7 nights min)
                          #7045797ha
                          1
                          Favorite
                            Viewed 6 times in the last 48 hours
                            Exceptional! 5/5
                            (9 reviews)
                            avg/night
                            (7 nights min)
                            #33938
                            9
                            Favorite
                              Viewed 11 times in the last 48 hours
                              avg/night
                              (7 nights min)
                              #4570625ha
                              Favorite
                                avg/night
                                (28 nights min)
                                #780762
                                Favorite
                                  avg/night
                                  (7 nights min)
                                  #937523
                                  Favorite
                                    Viewed 19 times in the last 48 hours
                                    Exceptional! 5/5
                                    (9 reviews)
                                    avg/night
                                    (6 nights min)
                                    #801416
                                    9
                                    Favorite
                                      Viewed 8 times in the last 48 hours
                                      Exceptional! 5/5
                                      (7 reviews)
                                      svg-lightning
                                      avg/night
                                      (7 nights min)
                                      #286201
                                      7
                                      Favorite
                                        Exceptional! 5/5
                                        (10 reviews)
                                        avg/night
                                        (28 nights min)
                                        #429489
                                        10
                                        Favorite
                                          avg/night
                                          (28 nights min)
                                          #745919
                                          Favorite
                                            avg/night
                                            (30 nights min)
                                            #152327
                                            Favorite
                                              avg/night
                                              (27 nights min)
                                              #3633231ha
                                              Favorite
                                                Viewed 5 times in the last 48 hours
                                                Exceptional! 5/5
                                                (30 reviews)
                                                avg/night
                                                (7 nights min)
                                                #370890
                                                30
                                                Favorite
                                                  View details for price
                                                  (28 nights min)
                                                  #1117904
                                                  Favorite
                                                    avg/night
                                                    (3 nights min)
                                                    #883030
                                                    Favorite
                                                      Viewed 5 times in the last 48 hours
                                                      avg/night
                                                      (3 nights min)
                                                      #883031
                                                      1
                                                      Favorite
                                                        Viewed 5 times in the last 48 hours
                                                        avg/night
                                                        (7 nights min)
                                                        #4555973ha
                                                        Favorite
                                                          Viewed 6 times in the last 48 hours
                                                          Exceptional! 5/5
                                                          (3 reviews)
                                                          avg/night
                                                          (7 nights min)
                                                          #173155
                                                          3
                                                          Favorite
                                                            Viewed 14 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (12 reviews)
                                                            avg/night
                                                            (7 nights min)
                                                            #189714
                                                            12
                                                            Favorite
                                                              Viewed 8 times in the last 48 hours
                                                              avg/night
                                                              (7 nights min)
                                                              #1109117
                                                              Favorite
                                                                Viewed 10 times in the last 48 hours
                                                                avg/night
                                                                (7 nights min)
                                                                #1136457
                                                                Favorite
                                                                  Viewed 7 times in the last 48 hours
                                                                  avg/night
                                                                  (7 nights min)
                                                                  #4543764ha
                                                                  Favorite
                                                                    avg/night
                                                                    (3 nights min)
                                                                    #883029
                                                                    Favorite
                                                                      Viewed 7 times in the last 48 hours
                                                                      avg/night
                                                                      (7 nights min)
                                                                      #4555994ha
                                                                      Favorite
                                                                        Viewed 20 times in the last 48 hours
                                                                        avg/night
                                                                        (7 nights min)
                                                                        #471432
                                                                        4
                                                                        Favorite
                                                                          Viewed 6 times in the last 48 hours
                                                                          avg/night
                                                                          (2 - 4 nights min)
                                                                          #746312
                                                                          2
                                                                          Favorite
                                                                            avg/night
                                                                            (28 nights min)
                                                                            #1108924
                                                                            Favorite
                                                                              Excellent! 4.3/5
                                                                              (8 reviews)
                                                                              avg/night
                                                                              (7 nights min)
                                                                              #72385
                                                                              8
                                                                              Favorite
                                                                                Viewed 9 times in the last 48 hours
                                                                                avg/night
                                                                                (7 nights min)
                                                                                #1125433
                                                                                Favorite
                                                                                  avg/night
                                                                                  (3 nights min)
                                                                                  #883028
                                                                                  Favorite
                                                                                    avg/night
                                                                                    (7 nights min)
                                                                                    #7044505ha
                                                                                    Favorite
                                                                                      avg/night
                                                                                      (28 nights min)
                                                                                      #689629
                                                                                      1
                                                                                      Favorite
                                                                                        Viewed 7 times in the last 48 hours
                                                                                        avg/night
                                                                                        (7 nights min)
                                                                                        #4555962ha
                                                                                        Favorite
                                                                                          avg/night
                                                                                          (3 nights min)
                                                                                          #883032
                                                                                          Favorite
                                                                                            Viewed 22 times in the last 48 hours
                                                                                            Exceptional! 5/5
                                                                                            (10 reviews)
                                                                                            avg/night
                                                                                            (4 - 7 nights min)
                                                                                            #209276
                                                                                            10
                                                                                            Favorite
                                                                                              avg/night
                                                                                              (3 nights min)
                                                                                              #883026
                                                                                              Favorite
                                                                                                avg/night
                                                                                                (3 nights min)
                                                                                                #883027
                                                                                                1
                                                                                                Favorite
                                                                                                  avg/night
                                                                                                  (3 nights min)
                                                                                                  #883033
                                                                                                  Favorite
                                                                                                    avg/night
                                                                                                    (7 nights min)
                                                                                                    #4555929ha
                                                                                                    Favorite
                                                                                                      Viewed 11 times in the last 48 hours
                                                                                                      avg/night
                                                                                                      (2 nights min)
                                                                                                      #294142ha
                                                                                                      1
                                                                                                       

                                                                                                      Recent Upper Matecumbe Key Reviews

                                                                                                      A True Resort at Home

                                                                                                      5 of 5
                                                                                                      This home has an appeal of a resort and the privacy of an estate. We had the pleasure to stay here from June 20 to June 27 2015. Upon arrival everything was clean and amenities abound. We rent vacation homes often and rarely do we find them as clean as this one. The location was perfect, good restaurants and activities nearby. Jo Anne has always been helpful since we travel with handicapped and have specific requirements. Of course we recommend this home and its beautiful property and location to all our friends as long as they don't choose the dates we wish for next year. After dining at the nearby restaurants and a one day trip to Key West it was great just to stay home one night and dine in, enjoying the atmosphere, view and comfort of Southern Comfort. The night after our arrival back home we stumbled upon a television series called "Bloodline" which takes place in Islamorada, so it felt as if we were extending our latest visit seeing the locations we just left. Once again I should mention the house was perfect for our Keys get away and the accommodations were magnificent, especially having the separate apartment. Looking forward to next year at Southern Comfort again.
                                                                                                      • Submitted: Jul 22, 2015
                                                                                                      • Stayed: Jun 2015

                                                                                                      Awesome Resort

                                                                                                      5 of 5
                                                                                                      The owner designed and captured what represents Floridian style. So much detail was put into the entire premises, walkways, lagoon style pool and into the Princess Palm we stayed in. This was my first time there and won't be my last! Staff from the office to maintenance of the premises were friendly but respectful of our privacy. The boat marina accomodations are top notch as well.
                                                                                                      • Submitted: May 31, 2013
                                                                                                      • Stayed: May 2013