Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

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 Online Payment(419)

419 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!
                  3 - 5 night minimum stay
                  • 1 BR,
                  • 1 BA,
                  • Sleeps 2
                    (33)
                    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,
                                • Sleeps 6
                                  (19)
                                  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,
                                      • 3 BA,
                                      • 1 HF BA,
                                      • Sleeps 8
                                        (17)
                                        Book it Now!
                                        1 - 7 night minimum stay
                                        • 3 BR,
                                        • 2 BA,
                                        • Sleeps 8
                                          (17)
                                          Book it Now!
                                          1 - 7 night minimum stay
                                          • 3 BR,
                                          • 3 BA,
                                          • 1 HF 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
                                                    • Studio,
                                                    • 1 BA,
                                                    • Sleeps 2
                                                      (18)
                                                      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)
                                                          Advertisement
                                                           

                                                          Recent Key West Reviews

                                                          Just right - comfortable, affordable, fun

                                                          4 of 5
                                                          My husband and I stayed for 3 nights and we made the most of it. Used hot tub, cooked out on the grill provided, brought our own bikes which we could safely store on the deck and rode all over starting with the bike path across the street, walked to beach, mimosas on the deck, and rainy day cuddling on the couch. It was instantly welcoming and comfortable. We did not want for anything. The location was great...an easy bike ride to Duval Street/Mallory Square or the management provided a handy book with information on where to find parking (they were spot-on). It is a really short bike ride down a wide path to Martello Tower & White Street pier. There is a beach within walking distance, but Key West is not known for its great beaches. There was also fishing gear available for us to use, a very nice touch.
                                                          • Submitted: Sep 20, 2014
                                                          • Stayed: Sep 2014

                                                          Claude Monet suite

                                                          4 of 5
                                                          Rating Details: The property manager was adequately helpful. The vacation rental was very clean. I was somewhat unhappy with the location. I was very satisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: Rental was very nice, nothing Claude Monet about it tho. Location want great and pools were two blocks away
                                                          • 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