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

Holidaymakers searching for holiday rentals in Islamorada also enquired about villas in Reunion, holiday homes in Key Largo and villas in Anna Maria

Make a holiday rental villa or apartment in Islamorada, Florida your home away from home

Nestled between the watery wilderness of the Everglades National Park and the natural wonders of North America’s only living coral reef is the village of Islamorada, spread across six islands of the Florida Keys, including Plantation Key, Windley Key, Upper and Lower Matecumbe Key, Indian Key and Lignumvitae Key. Known as the sport fishing capital of Florida, Islamorada attracts fishermen from around the world to try and catch a record sailfish.

Things to do in Islamorada, Florida

Islamorada is a world class fishing destination. The deep sea fishing is absolutely sensational, and the island is known as the world’s fishing capital. There are a huge range of captains ready to take budding fishermen out into the warm, turquoise waters of the Atlantic to catch huge sports fish, especially sailfish. After a great morning’s sport, you can head into the fishing backcountry of Islamorada to catch tarpon, bonefish, snook and redfish in the shallow salt waters.

However, there is far more to an Islamorada holiday than fishing if you want. The white sand Islamorada beaches are an absolute joy on which to relax, and despite the enchanting beauty of the Islamorada beaches, crowds are almost unheard of. During the evenings, live music can be heard wafting on the breeze, usually emanating from the open air Amphitheatre in Founder’s Park. Robbie’s Marina is a wonderful place to visit from Islamorada accommodation, especially if you have children with you as you can swim with dolphin and other aquatic animals in controlled conditions.

The beautifully natural interior of Islamorada is a magnificent place to explore in peace if you manage to drag yourself away from the glorious Islamorada beaches and the sea. There are a range of excellent nature trails to walk, providing a unique insight into both the natural and man made history of the islands. The Windley Key Fossil Reef Geological State Park and the Long Key State Park are particularly relaxing places to stroll from self catering Islamorada property rentals.

Places to visit on holiday in Islamorada, Florida

Just to the north of Islamorada is Key Largo, the northernmost of the Florida Keys. Key Largo is a particularly special place to visit from an Islamorada villa, as the interior of the island is a beautiful mix of hardwood forests, glistening corals and silent creeks. Scuba diving is particularly popular in the waters of the Atlantic too.

Weather in Islamorada, Florida

The weather in Islamorada is glorious year round. Regardless of whether you are looking to escape the British winter or are looking for the ultimate summer sun, a holiday rental in Islamorada is the ideal option. During June, July and August, daily temperatures routinely peak in the mid 30’s (˚C), whilst in the grips of winter, midday temperatures still peak in the high 20’s or low 30’s on a daily basis.

Travel to Islamorada, Florida

Virgin Atlantic and British Airways both provide direct flights from the UK to Miami’s International Airport (MIA). Upon your arrival at Miami, you can either drive across the bridges and islands of the Florida Keys or take a short hop flight to Key West (NQX).

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 40 times in the last 48 hours
    avg/night
    (30 nights minimum)
    House #441234vb
    4
    Favorite
      Viewed 36 times in the last 48 hours
      Excellent! 4.5/5
      (34 reviews)
      avg/night
      (6 nights minimum)
      Condo #454283vb
      34
      Favorite
        Viewed 9 times in the last 48 hours
        View details for price
        (28 nights minimum)
        Condo #873539vb
        1
        Favorite
          Viewed 47 times in the last 48 hours
          Excellent! 4.7/5
          (43 reviews)
          avg/night
          (7 nights minimum)
          Townhome #484134vb
          43
          Favorite
            Viewed 31 times in the last 48 hours
            avg/night
            (28 nights minimum)
            House #976088vb
            4
            Favorite
              Viewed 39 times in the last 48 hours
              Exceptional! 5/5
              (38 reviews)
              avg/night
              (7 nights minimum)
              House #614739vb
              38
              Favorite
                Viewed 60 times in the last 48 hours
                Exceptional! 5/5
                (27 reviews)
                avg/night
                (7 nights minimum)
                Condo #750103vb
                27
                Favorite
                  Viewed 15 times in the last 48 hours
                  Wonderful! 4.8/5
                  (23 reviews)
                  avg/night
                  (7 nights minimum)
                  House #4208345
                  23
                  Favorite
                    Viewed 6 times in the last 48 hours
                    Wonderful! 4.9/5
                    (14 reviews)
                    avg/night
                    (29 nights minimum)
                    House #979944vb
                    14
                    Favorite
                      Viewed 42 times in the last 48 hours
                      Exceptional! 5/5
                      (20 reviews)
                      avg/night
                      (7 nights minimum)
                      House #899629vb
                      20
                      Favorite
                        Viewed 23 times in the last 48 hours
                        avg/night
                        (30 nights minimum)
                        House #4034558
                        3
                        Favorite
                          Viewed 19 times in the last 48 hours
                          Premier Partner
                          Exceptional! 5/5
                          (45 reviews)
                          avg/night
                          (7 nights minimum)
                          House #426200vb
                          45
                          Favorite
                            Viewed 21 times in the last 48 hours
                            Exceptional! 5/5
                            (16 reviews)
                            avg/night
                            (28 nights minimum)
                            House #639492vb
                            16
                            Favorite
                              Viewed 15 times in the last 48 hours
                              Wonderful! 4.8/5
                              (12 reviews)
                              avg/night
                              (7 nights minimum)
                              House #307472
                              12
                              Favorite
                                Viewed 11 times in the last 48 hours
                                Premier Partner
                                Wonderful! 4.9/5
                                (16 reviews)
                                avg/night
                                (7 nights minimum)
                                Condo #863892vb
                                16
                                Favorite
                                  Viewed 9 times in the last 48 hours
                                  avg/night
                                  (28 nights minimum)
                                  House #190163vb
                                  3
                                  Favorite
                                    Viewed 17 times in the last 48 hours
                                    Wonderful! 4.8/5
                                    (26 reviews)
                                    avg/night
                                    (7 nights minimum)
                                    Condo #613561vb
                                    26
                                    Favorite
                                      Viewed 6 times in the last 48 hours
                                      avg/night
                                      (30 nights minimum)
                                      Townhome #1030281vb
                                      3
                                      Favorite
                                        Viewed 19 times in the last 48 hours
                                        Exceptional! 5/5
                                        (61 reviews)
                                        avg/night
                                        (7 nights minimum)
                                        Condo #50672vb
                                        61
                                        Favorite
                                          Viewed 16 times in the last 48 hours
                                          Premier Partner
                                          Wonderful! 4.8/5
                                          (39 reviews)
                                          avg/night
                                          (7 nights minimum)
                                          House #3970025
                                          39
                                          Favorite
                                            Viewed 22 times in the last 48 hours
                                            Premier Partner
                                            Exceptional! 5/5
                                            (12 reviews)
                                            avg/night
                                            (7 nights minimum)
                                            Estate #809744vb
                                            12
                                            Favorite
                                              Viewed 13 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (48 reviews)
                                              avg/night
                                              (7 nights minimum)
                                              Condo #77221vb
                                              48
                                              Favorite
                                                Viewed 39 times in the last 48 hours
                                                Exceptional! 5/5
                                                (9 reviews)
                                                avg/night
                                                (7 nights minimum)
                                                House #1041154vb
                                                9
                                                Favorite
                                                  Viewed 14 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (74 reviews)
                                                  avg/night
                                                  (7 nights minimum)
                                                  House #359378vb
                                                  74
                                                  Favorite
                                                    Viewed 17 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (69 reviews)
                                                    avg/night
                                                    (7 nights minimum)
                                                    House #648466vb
                                                    69
                                                    Favorite
                                                      Viewed 20 times in the last 48 hours
                                                      Excellent! 4.4/5
                                                      (33 reviews)
                                                      avg/night
                                                      (7 nights minimum)
                                                      Condo #9904vb
                                                      33
                                                      Favorite
                                                        Viewed 20 times in the last 48 hours
                                                        Premier Partner
                                                        Exceptional! 5/5
                                                        (16 reviews)
                                                        avg/night
                                                        (7 nights minimum)
                                                        Condo #49422vb
                                                        16
                                                        Favorite
                                                          Viewed 17 times in the last 48 hours
                                                          Very Good! 4.1/5
                                                          (11 reviews)
                                                          avg/night
                                                          (7 nights minimum)
                                                          House #3690813
                                                          11
                                                          Favorite
                                                            Viewed 15 times in the last 48 hours
                                                            Premier Partner
                                                            Exceptional! 5/5
                                                            (22 reviews)
                                                            avg/night
                                                            (7 nights minimum)
                                                            House #4249038
                                                            22
                                                            Favorite
                                                              Viewed 11 times in the last 48 hours
                                                              Good! 3.7/5
                                                              (6 reviews)
                                                              avg/night
                                                              (7 nights minimum)
                                                              Condo #690152vb
                                                              6
                                                              Favorite
                                                                Viewed 10 times in the last 48 hours
                                                                Premier Partner
                                                                Exceptional! 5/5
                                                                (62 reviews)
                                                                avg/night
                                                                (7 nights minimum)
                                                                House #326184
                                                                62
                                                                Favorite
                                                                  Viewed 15 times in the last 48 hours
                                                                  avg/night
                                                                  (28 nights minimum)
                                                                  House #1106150vb
                                                                  Favorite
                                                                    Viewed 7 times in the last 48 hours
                                                                    avg/night
                                                                    (28 nights minimum)
                                                                    House #789338vb
                                                                    Favorite
                                                                      Viewed 51 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (20 reviews)
                                                                      avg/night
                                                                      (7 nights minimum)
                                                                      House #12740vb
                                                                      20
                                                                      Favorite
                                                                        Viewed 8 times in the last 48 hours
                                                                        avg/night
                                                                        (29 nights minimum)
                                                                        House #1100567vb
                                                                        Favorite
                                                                          Viewed 13 times in the last 48 hours
                                                                          Wonderful! 4.8/5
                                                                          (26 reviews)
                                                                          avg/night
                                                                          (7 nights minimum)
                                                                          Condo #301565
                                                                          26
                                                                          Favorite
                                                                            Viewed 13 times in the last 48 hours
                                                                            Premier Partner
                                                                            Exceptional! 5/5
                                                                            (7 reviews)
                                                                            avg/night
                                                                            (7 nights minimum)
                                                                            Condo #735867vb
                                                                            7
                                                                            Favorite
                                                                              Viewed 11 times in the last 48 hours
                                                                              Wonderful! 4.8/5
                                                                              (39 reviews)
                                                                              avg/night
                                                                              (7 nights minimum)
                                                                              House #513264vb
                                                                              39
                                                                              Favorite
                                                                                Viewed 27 times in the last 48 hours
                                                                                Exceptional! 5/5
                                                                                (40 reviews)
                                                                                svg-lightning
                                                                                avg/night
                                                                                (28 nights minimum)
                                                                                House #671636vb
                                                                                40
                                                                                Favorite
                                                                                  Viewed 9 times in the last 48 hours
                                                                                  Excellent! 4.6/5
                                                                                  (15 reviews)
                                                                                  avg/night
                                                                                  (6 - 8 nights minimum)
                                                                                  House #729498vb
                                                                                  15
                                                                                  Favorite
                                                                                    Wonderful! 4.9/5
                                                                                    (34 reviews)
                                                                                    avg/night
                                                                                    (7 nights minimum)
                                                                                    House #3788659
                                                                                    34
                                                                                    Favorite
                                                                                      Viewed 10 times in the last 48 hours
                                                                                      Exceptional! 5/5
                                                                                      (6 reviews)
                                                                                      avg/night
                                                                                      (28 nights minimum)
                                                                                      House #4264853
                                                                                      6
                                                                                      Favorite
                                                                                        Viewed 9 times in the last 48 hours
                                                                                        Exceptional! 5/5
                                                                                        (7 reviews)
                                                                                        avg/night
                                                                                        (7 nights minimum)
                                                                                        Condo #788846vb
                                                                                        7
                                                                                        Favorite
                                                                                          Viewed 23 times in the last 48 hours
                                                                                          avg/night
                                                                                          (7 - 30 nights minimum)
                                                                                          Townhome #1139578vb
                                                                                          Favorite
                                                                                            Viewed 18 times in the last 48 hours
                                                                                            avg/night
                                                                                            (28 nights minimum)
                                                                                            Condo #868856vb
                                                                                            Favorite
                                                                                              Viewed 8 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (33 reviews)
                                                                                              avg/night
                                                                                              (6 nights minimum)
                                                                                              House #452120vb
                                                                                              33
                                                                                              Favorite
                                                                                                Viewed 10 times in the last 48 hours
                                                                                                Premier Partner
                                                                                                Exceptional! 5/5
                                                                                                (8 reviews)
                                                                                                avg/night
                                                                                                (7 nights minimum)
                                                                                                Condo #899855vb
                                                                                                8
                                                                                                Favorite
                                                                                                  Viewed 6 times in the last 48 hours
                                                                                                  Wonderful! 4.8/5
                                                                                                  (6 reviews)
                                                                                                  avg/night
                                                                                                  (28 nights minimum)
                                                                                                  Condo #3827390
                                                                                                  6
                                                                                                  Favorite
                                                                                                    Viewed 16 times in the last 48 hours
                                                                                                    Wonderful! 4.8/5
                                                                                                    (53 reviews)
                                                                                                    avg/night
                                                                                                    (7 nights minimum)
                                                                                                    House #944148
                                                                                                    53
                                                                                                    Favorite
                                                                                                      Viewed 7 times in the last 48 hours
                                                                                                      Premier Partner
                                                                                                      avg/night
                                                                                                      (7 nights minimum)
                                                                                                      Villa #4274178
                                                                                                      3

                                                                                                      Islamorada Holiday Homes & Rentals (300+)

                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      What a fantastic place to stay!

                                                                                                      5 of 5
                                                                                                      This condo has it all! It's one of the best situated in the Upper Keys area and the views from the balcony of the Gulf AND Atlantic Ocean were fantastic. It has all the comforts of home, is beautifully furnished with keysy colours. The whole apartment is very clean, light and refreshing. The grounds are nicely maintained and include a beautiful swimming pool that is larger than most and 2 tennis courts. Just a real nice place to be for relaxation, swimming in the pool, fishing in the Marina and snorkelling from the beach area. Lots of fine dining close by, cooked on the gas BBQ on the balcony a few nights! Brill!!. My wife and I totally enjoyed our stay at Susan and Richards condo. Decided to rent a boat for a few days and even had a dock provided for us by Susan. The owners could not have been more accommodating and genuinely friendly. No more small hotel rooms for us! we saved a lot of money and had every conceivable amenity (even an electric kettle!!) We highly recommend this apartment and are already planning our next trip there! Can't wait!!
                                                                                                      • Review Submitted: Sep 09, 2008
                                                                                                      • Date of Stay: Aug 2008