HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled

Make a holiday home, condo, villa or apartment in Key West, Florida your home away from home

Key West is the name of both a city and an island at the southern tip of the Florida Keys, to the south of Miami. The city is the southernmost city in the contiguous United States and has a tropical climate with sandy beaches, palm trees, beautiful sunsets, fishing, diving and plenty more to enjoy too! Key West holiday rentals come in all different shapes and sizes, from houseboats, to luxury condos, to traditional Southern homes, plus there’s numerous villas to rent in Key West too. A holiday in Key West is suitable for the whole family, couples, or groups of friends.

Things to do on holiday in Key West, Florida, USA

Holidays in Key West can be both fun and relaxing! With so much water around you it’s not surprising that water-based activities are popular. You can try all sorts of water sports here, from kayaking, to parasailing, to snorkelling. Boat trips are popular too, and numerous ones are available, to take you to the best fishing spots, or the best diving spots, or how about a glass bottomed boat cruise where you look out for dolphins? Talking of dolphins, swimming with dolphins is just one more of the activities you can enjoy here!

On dry land, there’s also plenty to see and do too. Take time out from your Key West holiday rental to visit the Key West Nature Preserve, journey on the Conch Train on a tour around the Old Town, and visit the Florida Keys Eco-Discovery Center. In the Old Town you’ll see the Ernest Hemmingway House, which you can visit, as well as other historical houses and buildings. After a day of sightseeing, relax and pamper yourself in one of the many Key West spas ready for a lively evening in one of the famous and popular bars of Key West, such as Sloppy Joe’s.

Places to visit on holiday in Key West, Florida, USA

There’s plenty to keep you occupied in Key West itself, but your Key West villa is also in easy reach of other places to visit too. Dry Tortugas National Park for example, is a group of seven islands situated about 70 miles off the Key West coast and accessible by ferry or seaplane. If you charter a boat there are numerous other islands of the coast of Key West to explore, or journey by car to the north towards Miami on Route 1, crossing the famous Seven Mile Bridge.

The weather in Key West, Florida, USA

There are villas to rent in Key West throughout the year to take advantage of the great tropical climate here! Warm temperatures will be experienced year round, though bear in mind there are two seasons in Key West – wet and dry. May to October is the wetter season, whilst November to April has a little rainfall, however, Key West is the driest city in Florida!

Flights to Key West, Florida, USA

Key West International Airport is the closest airport to your Key West holiday home, though flights to here are expensive. A better idea may be a flight to Miami, then rent a car and make the scenic drive down to Key West.

Cancel Clear Filters Apply Filters
More Filters

Price Per Night

£ £

Bedrooms

Bathrooms

Payment Options

Popular Searches

Facilities

Location Type

Local Area

Property Details

Clear Filters
Use filters to narrow your search results!
Favorite
    Viewed 37 times in the last 48 hours
    Wonderful! 4.9/5
    (96 reviews)
    avg/night
    96
    Favorite
      Viewed 121 times in the last 48 hours
      Wonderful! 4.8/5
      (5 reviews)
      avg/night
      5
      Favorite
        Viewed 77 times in the last 48 hours
        Wonderful! 4.9/5
        (88 reviews)
        avg/night
        88
        Favorite
          Viewed 57 times in the last 48 hours
          Wonderful! 4.8/5
          (17 reviews)
          avg/night
          17
          Favorite
            Viewed 214 times in the last 48 hours
            Wonderful! 4.9/5
            (16 reviews)
            avg/night
            16
            Favorite
              Viewed 21 times in the last 48 hours
              Wonderful! 4.9/5
              (76 reviews)
              avg/night
              76
              Favorite
                Viewed 62 times in the last 48 hours
                Excellent! 4.3/5
                (89 reviews)
                avg/night
                89
                Favorite
                  Viewed 29 times in the last 48 hours
                  Excellent! 4.6/5
                  (44 reviews)
                  avg/night
                  44
                  Favorite
                    Viewed 18 times in the last 48 hours
                    Exceptional! 5/5
                    (35 reviews)
                    avg/night
                    35
                    Favorite
                      Viewed 29 times in the last 48 hours
                      Wonderful! 4.9/5
                      (44 reviews)
                      avg/night
                      44
                      Favorite
                        Viewed 32 times in the last 48 hours
                        Wonderful! 4.9/5
                        (101 reviews)
                        avg/night
                        101
                        Favorite
                          Viewed 61 times in the last 48 hours
                          Wonderful! 4.9/5
                          (55 reviews)
                          avg/night
                          55
                          Favorite
                            Viewed 14 times in the last 48 hours
                            Wonderful! 4.8/5
                            (77 reviews)
                            avg/night
                            77
                            Favorite
                              Viewed 32 times in the last 48 hours
                              Wonderful! 4.9/5
                              (53 reviews)
                              avg/night
                              53
                              Favorite
                                Viewed 20 times in the last 48 hours
                                Wonderful! 4.8/5
                                (84 reviews)
                                avg/night
                                84
                                Favorite
                                  Viewed 12 times in the last 48 hours
                                  Wonderful! 4.8/5
                                  (84 reviews)
                                  avg/night
                                  84
                                  Favorite
                                    Viewed 17 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (49 reviews)
                                    avg/night
                                    49
                                    Favorite
                                      Viewed 37 times in the last 48 hours
                                      avg/night
                                      Favorite
                                        Viewed 25 times in the last 48 hours
                                        Wonderful! 4.8/5
                                        (28 reviews)
                                        avg/night
                                        28
                                        Favorite
                                          Viewed 32 times in the last 48 hours
                                          avg/night
                                          Favorite
                                            Viewed 12 times in the last 48 hours
                                            Excellent! 4.5/5
                                            (70 reviews)
                                            avg/night
                                            70
                                            Favorite
                                              Viewed 14 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (13 reviews)
                                              avg/night
                                              13
                                              Favorite
                                                Viewed 30 times in the last 48 hours
                                                Excellent! 4.5/5
                                                (10 reviews)
                                                avg/night
                                                10
                                                Favorite
                                                  Viewed 55 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (108 reviews)
                                                  avg/night
                                                  108
                                                  Favorite
                                                    Viewed 27 times in the last 48 hours
                                                    Exceptional! 5/5
                                                    (140 reviews)
                                                    avg/night
                                                    140
                                                    Favorite
                                                      Viewed 37 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (48 reviews)
                                                      avg/night
                                                      48
                                                      Favorite
                                                        Viewed 22 times in the last 48 hours
                                                        avg/night
                                                        Favorite
                                                          Viewed 41 times in the last 48 hours
                                                          Wonderful! 4.8/5
                                                          (17 reviews)
                                                          avg/night
                                                          17
                                                          Favorite
                                                            Viewed 23 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (49 reviews)
                                                            avg/night
                                                            49
                                                            Favorite
                                                              Viewed 39 times in the last 48 hours
                                                              Excellent! 4.6/5
                                                              (14 reviews)
                                                              avg/night
                                                              14
                                                              Favorite
                                                                Viewed 16 times in the last 48 hours
                                                                Excellent! 4.5/5
                                                                (44 reviews)
                                                                avg/night
                                                                44
                                                                Favorite
                                                                  Viewed 23 times in the last 48 hours
                                                                  Wonderful! 4.9/5
                                                                  (43 reviews)
                                                                  avg/night
                                                                  43
                                                                  Favorite
                                                                    Viewed 43 times in the last 48 hours
                                                                    Wonderful! 4.8/5
                                                                    (40 reviews)
                                                                    avg/night
                                                                    40
                                                                    Favorite
                                                                      Viewed 83 times in the last 48 hours
                                                                      Exceptional! 5/5
                                                                      (19 reviews)
                                                                      avg/night
                                                                      19
                                                                      Favorite
                                                                        Viewed 21 times in the last 48 hours
                                                                        Excellent! 4.5/5
                                                                        (22 reviews)
                                                                        avg/night
                                                                        22
                                                                        Favorite
                                                                          Viewed 42 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (27 reviews)
                                                                          avg/night
                                                                          27
                                                                          Favorite
                                                                            Viewed 19 times in the last 48 hours
                                                                            Wonderful! 4.8/5
                                                                            (29 reviews)
                                                                            avg/night
                                                                            29
                                                                            Favorite
                                                                              Viewed 21 times in the last 48 hours
                                                                              Excellent! 4.5/5
                                                                              (83 reviews)
                                                                              avg/night
                                                                              83
                                                                              Favorite
                                                                                Viewed 7 times in the last 48 hours
                                                                                Wonderful! 4.8/5
                                                                                (78 reviews)
                                                                                avg/night
                                                                                78
                                                                                Favorite
                                                                                  Viewed 27 times in the last 48 hours
                                                                                  Exceptional! 5/5
                                                                                  (7 reviews)
                                                                                  avg/night
                                                                                  7
                                                                                  Favorite
                                                                                    Viewed 16 times in the last 48 hours
                                                                                    Excellent! 4.7/5
                                                                                    (26 reviews)
                                                                                    avg/night
                                                                                    26
                                                                                    Favorite
                                                                                      Viewed 13 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (36 reviews)
                                                                                      avg/night
                                                                                      36
                                                                                      Favorite
                                                                                        Wonderful! 4.9/5
                                                                                        (36 reviews)
                                                                                        avg/night
                                                                                        36
                                                                                        Favorite
                                                                                          Viewed 39 times in the last 48 hours
                                                                                          avg/night
                                                                                          3
                                                                                          Favorite
                                                                                            Viewed 33 times in the last 48 hours
                                                                                            Excellent! 4.7/5
                                                                                            (11 reviews)
                                                                                            avg/night
                                                                                            11
                                                                                            Favorite
                                                                                              Viewed 22 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (35 reviews)
                                                                                              avg/night
                                                                                              35
                                                                                              Favorite
                                                                                                Viewed 29 times in the last 48 hours
                                                                                                Wonderful! 4.8/5
                                                                                                (71 reviews)
                                                                                                avg/night
                                                                                                71
                                                                                                Favorite
                                                                                                  Viewed 49 times in the last 48 hours
                                                                                                  Wonderful! 4.9/5
                                                                                                  (120 reviews)
                                                                                                  avg/night
                                                                                                  120
                                                                                                  Favorite
                                                                                                    Exceptional! 5/5
                                                                                                    (8 reviews)
                                                                                                    avg/night
                                                                                                    8
                                                                                                    Favorite
                                                                                                      Viewed 12 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (21 reviews)
                                                                                                      avg/night
                                                                                                      21