Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Key West Vacation Rentals with Pool(775)

775 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!
      7 night minimum stay
      • 2 BR,
      • 2 BA,
      • Sleeps 6
        (36)
        Book it Now!
        2 night minimum stay
        • 2 BR,
        • 2 BA,
        • Sleeps 4
          (34)
          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!
              7 night minimum stay
              • 1 BR,
              • 1 BA,
              • Sleeps 2
                (45)
                Book it Now!
                7 night minimum stay
                • 2 BR,
                • 1 BA,
                • Sleeps 4
                  (31)
                  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
                      (24)
                      7 night minimum stay
                      • 2 BR,
                      • 2 BA,
                      • Sleeps 6
                        (48)
                        4 night minimum stay
                        • 3 BR,
                        • 2 BA,
                        • Sleeps 8
                          (68)
                          Book it Now!
                          3 night minimum stay
                          • 2 BR,
                          • 2 BA,
                          • 1 HF BA,
                          • Sleeps 6
                            (24)
                            Book it Now!
                            3 - 5 night minimum stay
                            • 2 BR,
                            • 2 BA,
                            • 1 HF BA,
                            • Sleeps 4
                              (14)
                              Book it Now!
                              1 - 7 night minimum stay
                              • 2 BR,
                              • 2 BA,
                              • 1 HF BA,
                              • Sleeps 6
                                (17)
                                Book it Now!
                                1 - 7 night minimum stay
                                • 2 BR,
                                • 2 BA,
                                • 1 HF BA,
                                • Sleeps 6
                                  (17)
                                  Book it Now!
                                  1 - 7 night minimum stay
                                  • 3 BR,
                                  • 2 BA,
                                  • Sleeps 8
                                    (17)
                                    Book it Now!
                                    1 - 7 night minimum stay
                                    • 2 BR,
                                    • 2 BA,
                                    • Sleeps 6
                                      (18)
                                      Book it Now!
                                      1 - 7 night minimum stay
                                      • 3 BR,
                                      • 2 BA,
                                      • 1 HF BA,
                                      • Sleeps 8
                                        (22)
                                        Book it Now!
                                        1 - 7 night minimum stay
                                        • 1 BR,
                                        • 1 BA,
                                        • 1 HF BA,
                                        • Sleeps 4
                                          (16)
                                          Book it Now!
                                          1 - 7 night minimum stay
                                          • 2 BR,
                                          • 2 BA,
                                          • 1 HF BA,
                                          • Sleeps 7
                                            (15)
                                            Book it Now!
                                            1 - 7 night minimum stay
                                            • 1 BR,
                                            • 1 BA,
                                            • 1 HF BA,
                                            • Sleeps 4
                                              (15)
                                              Book it Now!
                                              1 - 7 night minimum stay
                                              • Studio,
                                              • 1 BA,
                                              • Sleeps 4
                                                (15)
                                                Book it Now!
                                                1 - 7 night minimum stay
                                                • 2 BR,
                                                • 2 BA,
                                                • 1 HF BA,
                                                • Sleeps 6
                                                  (13)
                                                  Book it Now!
                                                  1 - 7 night minimum stay
                                                  • 2 BR,
                                                  • 2 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 6
                                                    (13)
                                                    Book it Now!
                                                    1 - 7 night minimum stay
                                                    • 2 BR,
                                                    • 2 BA,
                                                    • 1 HF BA,
                                                    • Sleeps 6
                                                      (13)
                                                      Book it Now!
                                                      1 - 7 night minimum stay
                                                      • 1 BR,
                                                      • 1 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 4
                                                        (18)
                                                        Book it Now!
                                                        1 - 7 night minimum stay
                                                        • 3 BR,
                                                        • 2 BA,
                                                        • Sleeps 8
                                                          (13)
                                                          Advertisement
                                                           

                                                          Recent Key West Reviews

                                                          Clean and Peaceful townhome a 30 yards from Duval

                                                          5 of 5
                                                          The townhome was very clean and ready for us earlier than check-in. The neighbors were friendly and the garden area was quiet, well-kept. It is a 15 second walk to Duval, but set off on a side street where it is private. Will go through Key West Vacation Rentals on my next trip to Key West.
                                                          • Submitted: Sep 18, 2014
                                                          • Stayed: Sep 2014

                                                          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

                                                          Key West 2014

                                                          4 of 5
                                                          Rating Details: The property manager was more than helpful. The vacation rental was very clean. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: It was a nice stay overall. The condo was clean but needs to be updated very badly. Also the dryer makes a very LOUD noise, the rooster woke us up every day from 4:30am-8am other than that it was good. We love it in Key West but not sure if we would stay there again. We have stayed in the Pent House R19 last year and it was a nicer and bigger with a flat screen TV in master bedroom and no rooster to wake you up every morning. I would stay at R19 again but not R23.
                                                          • Submitted: Sep 16, 2014
                                                          • Stayed: Sep 2014