check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Summerland Key: Houses, Cottages & More (378)

  • 1 - 50 of 378
    • 2 BR
    • 2 BA
    • Sleeps 6
    57
      • 3 BR
      • 3 BA
      • Sleeps 6
      18
        • Studio
        • 4 BA
        • Sleeps 12
          • 4 BR
          • 3 BA
          • 2 HF BA
          • Sleeps 8
          2 Reviews
            • 3 BR
            • 2 BA
            • Sleeps 10
            9
              View details for price
              • 5 BR
              • 4 BA
              • Sleeps 12
              14
                • 5 BR
                • 4 BA
                • Sleeps 12
                5
                  View details for price
                  • 5 BR
                  • 4 BA
                  • 1 HF BA
                  • Sleeps 10
                  1 Review
                    • 4 BR
                    • 3 BA
                    • 1 HF BA
                    • Sleeps 10
                    4
                      • 2 BR
                      • 2 BA
                      • Sleeps 8
                      4
                        • 4 BR
                        • 2 BA
                        • Sleeps 8
                        21
                          • 3 BR
                          • 3 BA
                          • Sleeps 6
                          5
                            • 3 BR
                            • 3 BA
                            • 1 HF BA
                            • Sleeps 6
                            16
                              • 2 BR
                              • 2 BA
                              • Sleeps 4
                                • 3 BR
                                • 2 BA
                                • Sleeps 6
                                5
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 6
                                  8
                                    • 2 BR
                                    • 2 BA
                                    • 1 HF BA
                                    • Sleeps 8
                                    40
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 10
                                      1 Review
                                        • 5 BR
                                        • 3 BA
                                        • 1 HF BA
                                        • Sleeps 12
                                        1 Review
                                          • 5 BR
                                          • 3 BA
                                          • Sleeps 10
                                          1 Review
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 4
                                            13
                                              • 5 BR
                                              • 4 BA
                                              • Sleeps 10
                                                • 5 BR
                                                • 3 BA
                                                • Sleeps 10
                                                3
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 5
                                                    • 5 BR
                                                    • 4 BA
                                                    • Sleeps 14
                                                      • 5 BR
                                                      • 3 BA
                                                      • Sleeps 11
                                                        • 4 BR
                                                        • 3 BA
                                                        • Sleeps 10
                                                        12
                                                          • 3 BR
                                                          • 3 BA
                                                          • Sleeps 8
                                                          2 Reviews
                                                            • 5 BR
                                                            • 5 BA
                                                            • Sleeps 10
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                13
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 6
                                                                      40
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        24
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          32
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              8
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 5
                                                                                29
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 5
                                                                                    11
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 5
                                                                                      11
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        2 Reviews
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 6
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 4
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 7
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 6
                                                                                                13
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 6
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 8
                                                                                                    • 1 - 50 of 378
                                                                                                     

                                                                                                    Recent Summerland Key Reviews

                                                                                                    We had a great time

                                                                                                    5 of 5
                                                                                                    We seen the pictures when we purchased the week stay and thought it looked alright. When we arrived and walked in we were very pleased. The place was very clean, nicely arranged, and comfortable. For the money you truly couldn't go wrong. The fact that you can keep your boat in the channel 15ft from your house is worth the price alone. The community is nice, clean , and friendly. There is a small store there where you can fuel your boat among other things. My wife and kids used the pool and hot tub and I never heard a complaint from them. I plan on more visits to this house in the very near future. I give my stay 5 stars.
                                                                                                    • Submitted: Jul 5, 2016
                                                                                                    • Stayed: Jun 2016

                                                                                                    As Advertised - Responsive Owner - Great Time

                                                                                                    5 of 5
                                                                                                    We stayed at Summerland Estate for a week and had a great time. Property was as advertised, well-maintained, and comfortable. We only had one issue - problem with the microwave - owner responded immediately and had a new microwave installed. I'd give the property itself four stars + and our stay FIVE stars !
                                                                                                    • Submitted: May 31, 2016
                                                                                                    • Stayed: May 2016

                                                                                                    Another great Keys vacation!

                                                                                                    5 of 5
                                                                                                    Been vacationing in the Lower Keys for years, mostly staying on Little Torch Key. Decided to go a few miles down the road for this house because of the spa/pool to cool off in at end of day (much better than a hot tub in the Florida weather). We enjoyed it very much. The house is nice and super clean and we loved the proximity to the Square Grouper restaurant. Not cheap, as others have mentioned, but well worth the price for a great meal every time. Nice, quiet residential location and close enough for a day trip to Key West. Would recommend to anyone looking for a nice place to say.
                                                                                                    • Submitted: May 21, 2016
                                                                                                    • Stayed: May 2016