Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Florida Keys Waterfront Vacation Rentals Vacation Rentals(1,621)

1,621 Results
Book it Now!
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
    (41)
    Book it Now!
    3 - 7 night minimum stay
    • 2 BR,
    • 2 BA,
    • Sleeps 6
      (82)
      Book it Now!
      28 night minimum stay
      • 2 BR,
      • 2 BA,
      • Sleeps 6
        (91)
        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!
              2 night minimum stay
              • 2 BR,
              • 2 BA,
              • Sleeps 4
                (34)
                Book it Now!
                7 - 29 night minimum stay
                • 2 BR,
                • 2 BA,
                • 1 HF BA,
                • Sleeps 6
                  (57)
                  Book it Now!
                  4 - 7 night minimum stay
                  • 2 BR,
                  • 2 BA,
                  • Sleeps 5
                    (23)
                    Book it Now!
                    3 night minimum stay
                    • 1 BR,
                    • 1 BA,
                    • Sleeps 4
                      (38)
                      Book it Now!
                      4 - 5 night minimum stay
                      • 2 BR,
                      • 2 BA,
                      • Sleeps 7
                        (15)
                        Book it Now!
                        7 night minimum stay
                        • 3 BR,
                        • 3 BA,
                        • Sleeps 8
                          (21)
                          Book it Now!
                          3 night minimum stay
                          • 2 BR,
                          • 2 BA,
                          • Sleeps 8
                            (34)
                            7 night minimum stay
                            • 3 BR,
                            • 3 BA,
                            • Sleeps 8
                              (28)
                              Book it Now!
                              3 - 5 night minimum stay
                              • 1 BR,
                              • 1 BA,
                              • Sleeps 4
                                (24)
                                Book it Now!
                                7 night minimum stay
                                • 4 BR,
                                • 4 BA,
                                • Sleeps 10
                                  (8)
                                  7 night minimum stay
                                  • 2 BR,
                                  • 2 BA,
                                  • Sleeps 6
                                    (48)
                                    Book it Now!
                                    7 night minimum stay
                                    • 3 BR,
                                    • 3 BA,
                                    • Sleeps 8
                                      (12)
                                      Book it Now!
                                      6 night minimum stay
                                      • 3 BR,
                                      • 3 BA,
                                      • Sleeps 6
                                        (16)
                                        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)
                                            Book it Now!
                                            7 night minimum stay
                                            • 2 BR,
                                            • 2 BA,
                                            • 1 HF BA,
                                            • Sleeps 6
                                              (12)
                                              $1,900 - $2,600
                                              per week
                                              Book it Now!
                                              7 night minimum stay
                                              • 3 BR,
                                              • 2 BA,
                                              • 1 HF BA,
                                              • Sleeps 6
                                                (12)
                                                Book it Now!
                                                7 night minimum stay
                                                • 2 BR,
                                                • 2 BA,
                                                • 1 HF BA,
                                                • Sleeps 6
                                                  (12)
                                                  Book it Now!
                                                  7 night minimum stay
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • Sleeps 6
                                                    (14)
                                                    7 night minimum stay
                                                    • 2 BR,
                                                    • 2 BA,
                                                    • Sleeps 5
                                                      (16)
                                                      Book it Now!
                                                      28 - 30 night minimum stay
                                                      • 3 BR,
                                                      • 2 BA,
                                                      • Sleeps 6
                                                        (23)
                                                        Book it Now!
                                                        3 night minimum stay
                                                        • 2 BR,
                                                        • 2 BA,
                                                        • Sleeps 6
                                                          (12)
                                                           

                                                          Recent Florida Keys Reviews

                                                          Perfect Place away from the crazy Duval St scene.

                                                          5 of 5
                                                          This property is about 10 min away from Duval St. You can come home to an immaculate unit and get a good night's rest after a night in old town. The pool is right outside your door, there's a great little kitchen, and the whole unit has everything you need. Puts a hotel to shame. The front office staff are friendly and helpful and you can get discount coupons for food and attractions from them. Its a quick drive to the pharmacy and food stores, car rentals, etc. The marina bar is quaint and fun and a short stroll away from your unit. You also get a dedicated parking space. No car? Jump on the 2 provided bikes and explore the island. This was my girlfriend and l's first time in Key West. We will be back and Steve's unit will be where we will stay.
                                                          • Submitted: Sep 16, 2014
                                                          • Stayed: Sep 2014

                                                          Family Vaca

                                                          5 of 5
                                                          We rented this home August 2013. Lobster season had just begun. We had one toddler and a puppy along with 7 adults. We were perfectly comfortable. The bedrooms were comfy. Three are incredibly large, one is smaller with the bathroom in the hall. One bedroom has outdoor access. The kitchen has everything you'll need. The living room is small but right off the water and there was never an issue about space. There is an alarm on the door so if your small child opens it, you'll know immediately. Good safety feature for people with little ones. We turned it off when we were all together and our son was well supervised. The deck is great, very peaceful. Goes way out into the water and feels private. We took the kayaks out and had a great time looking in at the other homes along the water. Really a great place. We'd definitely rent there again.
                                                          • Submitted: Sep 13, 2014
                                                          • Stayed: Sep 2013

                                                          Superb place in the Keys.

                                                          5 of 5
                                                          The condo was exactly as described and very well stocked with bedding, towels and kitchen utensils. The view was to die for and we witnessed some very impressive lightening displays. We used the dock as we hired a boat for a few days and fished there in the evenings. There are some good restaurants close to the condo although we were very disappointed with the quality of food at the Island Fish Market. For most of our stay we had the pool to ourselves which was lovely. The grounds are teaming with wildlife and there are some lovely green iguanas in residence. This is a fantastic property and in an excellent location for visiting Key West. I highly recommend Janet's delightful condo to anyone and Janet herself could not have been more helpful.
                                                          • Submitted: Sep 2, 2014
                                                          • Stayed: Aug 2014