Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Boats
Bungalows
Cabins
Condos
Cottages
Estates
Homes
Lodges
Studios
Townhomes
Villas
Yachts
Barns
Castles
Chalets
Farmhouses
Hotels

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Florida Keys Vacation Rentals(889)

889 Results
Book it Now!
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
    (40)
    Book it Now!
    28 night minimum stay
    • 2 BR,
    • 2 BA,
    • Sleeps 6
      (91)
      Book it Now!
      3 - 7 night minimum stay
      • 2 BR,
      • 2 BA,
      • Sleeps 6
        (81)
        Book it Now!
        7 night minimum stay
        • 2 BR,
        • 2 BA,
        • Sleeps 6
          (36)
          Book it Now!
          4 - 7 night minimum stay
          • 2 BR,
          • 2 BA,
          • Sleeps 6
            (34)
            Book it Now!
            3 - 7 night minimum stay
            • 2 BR,
            • 1 BA,
            • Sleeps 5
              (27)
              Book it Now!
              7 - 29 night minimum stay
              • 2 BR,
              • 2 BA,
              • 1 HF BA,
              • Sleeps 6
                (56)
                Book it Now!
                4 - 7 night minimum stay
                • 2 BR,
                • 2 BA,
                • Sleeps 5
                  (23)
                  Book it Now!
                  7 night minimum stay
                  • 2 BR,
                  • 1 BA,
                  • Sleeps 4
                    (28)
                    Book it Now!
                    7 night minimum stay
                    • 2 BR,
                    • 1 BA,
                    • Sleeps 4
                      (65)
                      Book it Now!
                      3 night minimum stay
                      • 1 BR,
                      • 1 BA,
                      • Sleeps 4
                        (38)
                        Book it Now!
                        7 night minimum stay
                        • 1 BR,
                        • 1 BA,
                        • Sleeps 2
                          (45)
                          Book it Now!
                          3 - 13 night minimum stay
                          • 3 BR,
                          • 3 BA,
                          • Sleeps 8
                            (17)
                            Book it Now!
                            4 - 5 night minimum stay
                            • 2 BR,
                            • 2 BA,
                            • Sleeps 6
                              (13)
                              Book it Now!
                              7 night minimum stay
                              • 3 BR,
                              • 3 BA,
                              • Sleeps 8
                                (21)
                                Book it Now!
                                7 night minimum stay
                                • 2 BR,
                                • 1 BA,
                                • Sleeps 4
                                  (31)
                                  Book it Now!
                                  3 night minimum stay
                                  • 2 BR,
                                  • 2 BA,
                                  • Sleeps 8
                                    (34)
                                    Book it Now!
                                    7 night minimum stay
                                    • 2 BR,
                                    • 2 BA,
                                    • 1 HF BA,
                                    • Sleeps 5
                                      (24)
                                      Book it Now!
                                      3 - 5 night minimum stay
                                      • 1 BR,
                                      • 1 BA,
                                      • Sleeps 2
                                        (30)
                                        Book it Now!
                                        7 night minimum stay
                                        • 2 BR,
                                        • 2 BA,
                                        • Sleeps 4
                                          (40)
                                          Book it Now!
                                          3 - 5 night minimum stay
                                          • 1 BR,
                                          • 1 BA,
                                          • Sleeps 4
                                            (23)
                                            7 night minimum stay
                                            • 2 BR,
                                            • 2 BA,
                                            • Sleeps 6
                                              (47)
                                              Book it Now!
                                              7 night minimum stay
                                              • 3 BR,
                                              • 3 BA,
                                              • Sleeps 8
                                                (12)
                                                Book it Now!
                                                3 night minimum stay
                                                • 3 BR,
                                                • 3 BA,
                                                • Sleeps 8
                                                  (16)
                                                  4 night minimum stay
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • Sleeps 8
                                                    (68)
                                                    Book it Now!
                                                    7 night minimum stay
                                                    • 2 BR,
                                                    • 2 BA,
                                                    • Sleeps 6
                                                      (14)
                                                      Book it Now!
                                                      7 night minimum stay
                                                      • 2 BR,
                                                      • 2 BA,
                                                      • Sleeps 6
                                                        (12)
                                                         

                                                        Recent Florida Keys Reviews

                                                        Incredible vacation Rental!!!

                                                        5 of 5
                                                        We have stayed in MANY townhouses in Truman Annex, Flip-flop was by far the best experience yet!!! Beautiful, clean and well-stocked home that made the vacation so comfortable. Having the pool right behind the townhouse was such a plus...we would hit the beach for a couple hours and then jump into the pool before getting ready for dinner. Ward was awesome from the beginning of the process to the very end. Will definitely be returning!!!!
                                                        • Submitted: Aug 30, 2014
                                                        • Stayed: Jul 2014

                                                        Truly a crown jewel

                                                        5 of 5
                                                        This condo is in a perfect location. We have been to key west and stayed in many places on the island and this was definitely one of our best trips. You are within biking distance to everything. The oceanfront views are amazing. The condo is beautifully decorated and very comfortable. The balcony patio is quite spacious. The kitchen is fully equipped. The owner was wonderful to work with. We will definitely return again.
                                                        • Submitted: Aug 28, 2014
                                                        • Stayed: May 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