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Upper Florida Keys Vacation Home Rentals(379)

379 Results
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7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
    Book it Now!
    7 night minimum stay
    • 3 BR,
    • 2 BA,
    • Sleeps 8
      30 night minimum stay
      • 4 BR,
      • 3 BA,
      • Sleeps 8
        Book it Now!
        4 - 5 night minimum stay
        • 4 BR,
        • 4 BA,
        • Sleeps 14
          (13)
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          7 night minimum stay
          • 2 BR,
          • 2 BA,
          • 1 HF BA,
          • Sleeps 6
            (3)
            4 night minimum stay
            • 3 BR,
            • 2 BA,
            • Sleeps 8
              (7)
              Book it Now!
              7 night minimum stay
              • 4 BR,
              • 3 BA,
              • 1 HF BA,
              • Sleeps 8
                7 night minimum stay
                • 3 BR,
                • 2 BA,
                • 2 HF BA,
                • Sleeps 6
                  (17)
                  3 night minimum stay
                  • 2 BR,
                  • 1 BA,
                  • Sleeps 4
                    (45)
                    5 night minimum stay
                    • 2 BR,
                    • 1 BA,
                    • Sleeps 4
                      1 Review
                      7 night minimum stay
                      • 3 BR,
                      • 2 BA,
                      • Sleeps 6
                        (15)
                        $1,100 - $1,100
                        per week
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                        7 night minimum stay
                        • 4 BR,
                        • 2 BA,
                        • Sleeps 9
                          (11)
                          Book it Now!
                          7 night minimum stay
                          • 3 BR,
                          • 2 BA,
                          • Sleeps 8
                            (4)
                            7 night minimum stay
                            • 5 BR,
                            • 3 BA,
                            • Sleeps 10
                              (41)
                              29 night minimum stay
                              • 4 BR,
                              • 4 BA,
                              • Sleeps 10
                                (10)
                                28 night minimum stay
                                • 3 BR,
                                • 3 BA,
                                • Sleeps 8
                                  (5)
                                  7 night minimum stay
                                  • 3 BR,
                                  • 2 BA,
                                  • Sleeps 6
                                    (4)
                                    7 night minimum stay
                                    • 6 BR,
                                    • 4 BA,
                                    • 1 HF BA,
                                    • Sleeps 16
                                      (24)
                                      7 night minimum stay
                                      • 3 BR,
                                      • 3 BA,
                                      • Sleeps 8
                                        (23)
                                        28 night minimum stay
                                        • 3 BR,
                                        • 2 BA,
                                        • Sleeps 6
                                          (7)
                                          30 night minimum stay
                                          • 4 BR,
                                          • 4 BA,
                                          • 1 HF BA,
                                          • Sleeps 8
                                            (4)
                                            3 - 28 night minimum stay
                                            • 3 BR,
                                            • 3 BA,
                                            • Sleeps 8
                                              21 night minimum stay
                                              • 3 BR,
                                              • 1 BA,
                                              • 1 HF BA,
                                              • Sleeps 6
                                                • 2 BR,
                                                • 1 BA,
                                                • Sleeps 4
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 7
                                                    (26)
                                                    • 1 BR,
                                                    • 1 BA,
                                                    • Sleeps 3
                                                      • 4 BR,
                                                      • 3 BA,
                                                      • Sleeps 8
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                                                        7 night minimum stay
                                                        • 5 BR,
                                                        • 4 BA,
                                                        • Sleeps 12
                                                          (39)
                                                          Book it Now!
                                                          7 night minimum stay
                                                          • 3 BR,
                                                          • 2 BA,
                                                          • Sleeps 8
                                                            (16)
                                                            Book it Now!
                                                            3 night minimum stay
                                                            • 3 BR,
                                                            • 2 BA,
                                                            • Sleeps 10
                                                              (9)
                                                               

                                                              Recent Upper Florida Keys Reviews

                                                              Great place for families & the serious fisherman

                                                              5 of 5
                                                              What a lovely house! This is our 14th year going to Islamorada (Lower Matecumbe) area. We'd been renting the same place for years but the owners were using it. Finding a new place was a bit daunting! The house is on a pie-shaped lot, so the front of the house appears small but the gates open up to a huge back patio & yard area. There are several little seating areas, 2 big tables w/chairs & a couple of chaises. The dockage was very generous; we had our 27ft. Contender & 18ft. flats boat with plenty of room. There is everything you could want to make your fishing easy; electricity & water to the dock, a fish cleaning table in the shade and a storage room for your goodies with an extra refrigerator. The downstairs bedroom is perfect for teenagers. Laundry room downstairs as well with a large washer & dryer. Upstairs is a beautiful, comfortable living room & a big breakfast bar. There is a nice dining area plus little seating area that overlook the canal. All you need is right in the kitchen so you cook your catch. I usually cook every night & it was a pleasure. The bedrooms are on the smaller side, but plenty of room to put away your clothing, big closets & very comfortable beds. Master bath was lovely with a big whirlpool tub. There were plenty of towels & linens & all the incidentals were supplied- toilet tissue, paper towels, garbage bags, etc. There were also 2 paddle boards, which everyone used & really enjoyed. The view of the sunset from the dock was great. We had an older lady with us who spent much of her time sitting by the big windows, reading & watching the boats go by. She loved it. There is a nice shallow water/beach area nearby where people pull their boats up & swim; it's great for kids. There are 2 places nearby for boat gas & a hardware store & Habanos restaurant w/i walking distance. The owner, Rick, met my husband there upon arrival to answer any questions & explain where everything was. He was very nice & a great host. We had a great time & hope to return next year!
                                                              • Submitted: Aug 24, 2014
                                                              • Stayed: Jul 2014

                                                              Can't wait to come back next year!

                                                              5 of 5
                                                              We just got back from our stay at Summer Breezes and we cannot say enough great things about the property! The home was even better than it looked in the pictures; very clean, up to date, beautifully decorated and was stocked with anything you could possibly need for a comfortable stay. Tom and Mark were both very attentive and easy to work with. We had a seven adults and two babies in the house and there was plenty of space for everyone. The walk-in pool was perfect for the little ones and we had plenty of room on the dock for both of our boats. The ice maker was a big hit with us whether it was used for our cocktails or filling up our coolers for our fresh catch. We will definitely be booking this house again next year! Thanks again for a great trip!
                                                              • Submitted: Aug 22, 2014
                                                              • Stayed: Aug 2014

                                                              Lots of little extras

                                                              5 of 5
                                                              Very well thought out for the family oriented vacation. Spacious and comfortable. Owner seems to be conscious of need to maintain and upgrade. Waterways are beautiful and house is close to many attractions. Very convenient for all your needs
                                                              • Submitted: Aug 15, 2014
                                                              • Stayed: Aug 2014