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Upper Florida Keys Vacation Home Rentals(381)

381 Results
Book it Now!
4 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
    (23)
    Book it Now!
    6 night minimum stay
    • 3 BR,
    • 3 BA,
    • Sleeps 6
      (16)
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      7 night minimum stay
      • 2 BR,
      • 2 BA,
      • 1 HF BA,
      • Sleeps 6
        (12)
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        7 night minimum stay
        • 3 BR,
        • 2 BA,
        • Sleeps 6
          (14)
          Book it Now!
          7 night minimum stay
          • 2 BR,
          • 2 BA,
          • 1 HF BA,
          • Sleeps 5
            (12)
            Book it Now!
            7 night minimum stay
            • 2 BR,
            • 2 BA,
            • 1 HF BA,
            • Sleeps 6
              (14)
              7 night minimum stay
              • 2 BR,
              • 2 BA,
              • 1 HF BA,
              • Sleeps 5
                (19)
                Book it Now!
                7 night minimum stay
                • 2 BR,
                • 2 BA,
                • 1 HF BA,
                • Sleeps 4
                  (5)
                  28 night minimum stay
                  • 4 BR,
                  • 3 BA,
                  • Sleeps 8
                    (29)
                    3 - 5 night minimum stay
                    • 2 BR,
                    • 2 BA,
                    • Sleeps 9
                      (6)
                      7 night minimum stay
                      • 4 BR,
                      • 4 BA,
                      • Sleeps 8
                        (15)
                        7 night minimum stay
                        • 2 BR,
                        • 2 BA,
                        • 1 HF BA,
                        • Sleeps 6
                          (32)
                          7 night minimum stay
                          • 4 BR,
                          • 3 BA,
                          • Sleeps 12
                            (12)
                            Book it Now!
                            28 night minimum stay
                            • 2 BR,
                            • 3 BA,
                            • Sleeps 10
                              Book it Now!
                              3 - 5 night minimum stay
                              • 4 BR,
                              • 3 BA,
                              • Sleeps 10
                                2 - 3 night minimum stay
                                • 3 BR,
                                • 3 BA,
                                • 1 HF BA,
                                • Sleeps 8
                                  1 Review
                                  5 night minimum stay
                                  • 2 BR,
                                  • 2 BA,
                                  • Sleeps 6
                                    (25)
                                    7 night minimum stay
                                    • 2 BR,
                                    • 2 BA,
                                    • 1 HF BA,
                                    • Sleeps 6
                                      (24)
                                      7 night minimum stay
                                      • 4 BR,
                                      • 3 BA,
                                      • Sleeps 8
                                        2 Reviews
                                        7 night minimum stay
                                        • 3 BR,
                                        • 4 BA,
                                        • Sleeps 8
                                          (9)
                                          28 night minimum stay
                                          • 5 BR,
                                          • 3 BA,
                                          • Sleeps 16
                                            (27)
                                            28 night minimum stay
                                            • 7 BR,
                                            • 5 BA,
                                            • Sleeps 24
                                              (24)
                                              • 3 BR,
                                              • 3 BA,
                                              • Sleeps 6
                                                (12)
                                                1 - 28 night minimum stay
                                                • 4 BR,
                                                • 5 BA,
                                                • Sleeps 10
                                                  (4)
                                                  Book it Now!
                                                  5 - 7 night minimum stay
                                                  • 4 BR,
                                                  • 4 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 10
                                                    (3)
                                                    7 night minimum stay
                                                    • 3 BR,
                                                    • 2 BA,
                                                    • Sleeps 7
                                                      (27)
                                                      Book it Now!
                                                      30 night minimum stay
                                                      • 2 BR,
                                                      • 2 BA,
                                                      • Sleeps 4
                                                        (7)
                                                        3 - 7 night minimum stay
                                                        • 5 BR,
                                                        • 5 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 12
                                                          (3)
                                                          $18,000
                                                          per month
                                                          28 night minimum stay
                                                          • Studio,
                                                          • 6 BA,
                                                          • Sleeps 27
                                                            (7)
                                                            3 - 4 night minimum stay
                                                            • 5 BR,
                                                            • 3 BA,
                                                            • 1 HF BA,
                                                            • Sleeps 12
                                                              (5)
                                                               

                                                              Recent Upper Florida Keys Reviews

                                                              BEAUTIFUL AMAZING WONDERFUL STAY!!!!!

                                                              5 of 5
                                                              We rented for my daughters 33rd birthday, The home was very beautifully decorated and very clean. Everything was in its place washer and dryer were perfect the rooms were comfortable , The owner was pleasant and very helpful. The elevator was a plus due to my husbands knee issues so this is a great home if you have any problems going up or down stairs very accommodating. The area is fantastic and you have everything in walking distance if you need it. Love the peaceful area , We definitely would plan to go back again. THANK YOU
                                                              • Submitted: Sep 4, 2014
                                                              • Stayed: Aug 2014

                                                              Quiet and Relaxing

                                                              5 of 5
                                                              WOW, where do I start? Great place, many amenities, fishing poles, snorkel equipment, kayaks, canoes. Swimming/snorkeling/fishing right out back of cabin. Caught several fish, great fun. Close to Winn Dixie, many restaurants. The Spanish House restaurant in Islamorada is exceptional. The cabin is very comfy. Had all of the cookware we could possibly need. The beds are AWESOME!!! Decks great for watching sunrise. Sadly I am back at work, wishing we were still there.
                                                              • Submitted: Aug 27, 2014
                                                              • Stayed: Aug 2014

                                                              Great vacation, great house, great owner!

                                                              5 of 5
                                                              We did a 4 weeks tour in Florida (Siesta Key, Naples, Miami, Islamorada, Cocoa Beach and Orlando), Islamorada was the favorite destination of the whole family. We loved Angler's Reef, as it is just a small community, built and decorated in a very charming way and all the people we met were really nice. We also really liked the house, it is very well equipped, the beds are totally comfortable, no detail has been overlooked, it is so much better than staying in an impersonal hotel. Scott writes service with a capital S: it started from the moment I sent him the first email (he answered all correspondences in record time), the fact that he wants to be contacted upon arrival (he really wants to be sure that you have a perfect stay), all little extras the house is equipped with (salt, pepper, lots of different spices, liquid soap, coffee and tea for the first days, name anything you need at home and this house has it), plus the bathroom starter set (bigger than what you get in a 5 star hotel), to the very fast return of our deposit. It actually felt if we were staying in the house of a friend, not of a stranger. Make sure you visit the Turtle Hospital, swim with the dolphins either in Islamorada or Key Largo, go to the Dry Tortugas with the water plane (expensive but well worth the money), go fishing and eat Key lime pie. We also did a family photo session with Jannette de Llanos who makes great pics. Thank you Scott for contributing to the fantastic holidays we had, we will recommend this house to all our Swiss and Dutch family and friends and hope one day we will return! Kind regards, the Schönhaar family
                                                              • Submitted: Aug 24, 2014
                                                              • Stayed: Aug 2014