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Summerland Key Vacation Rentals with Parking Included(50)

50 Results
Book it Now!
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
    (12)
    7 night minimum stay
    • 5 BR,
    • 4 BA,
    • Sleeps 12
      (10)
      6 night minimum stay
      • 4 BR,
      • 3 BA,
      • 2 HF BA,
      • Sleeps 10
        1 Review
        • 2 BR,
        • 2 BA,
        • Sleeps 8
          (15)
          31 night minimum stay
          • 2 BR,
          • 2 BA,
          • Sleeps 8
            (3)
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            7 night minimum stay
            • 3 BR,
            • 3 BA,
            • Sleeps 6
              2 Reviews
              • 3 BR,
              • 2 BA,
              • Sleeps 10
                (7)
                30 night minimum stay
                • 2 BR,
                • 2 BA,
                • Sleeps 4
                  28 night minimum stay
                  • 2 BR,
                  • 2 BA,
                  • Sleeps 8
                    6 - 7 night minimum stay
                    • 2 BR,
                    • 2 BA,
                    • 1 HF BA,
                    • Sleeps 8
                      (35)
                      6 night minimum stay
                      • 3 BR,
                      • 2 BA,
                      • Sleeps 6
                        (3)
                        • 4 BR,
                        • 2 BA,
                        • Sleeps 12
                          $9,450
                          per month
                          28 night minimum stay
                          • 3 BR,
                          • 3 BA,
                          • Sleeps 6
                            28 night minimum stay
                            • 3 BR,
                            • 2 BA,
                            • Sleeps 8
                              7 - 31 night minimum stay
                              • 3 BR,
                              • 2 BA,
                              • Sleeps 7
                                (5)
                                35 more choices from the HomeAway Network
                                $3,750
                                per month
                                Book it Now!
                                28 night minimum stay
                                • 3 BR,
                                • 2 BA,
                                • Sleeps 6
                                  (3)
                                  Book it Now!
                                  28 night minimum stay
                                  • 2 BR,
                                  • 1 BA,
                                  • Sleeps 4
                                    2 Reviews
                                    Book it Now!
                                    14 night minimum stay
                                    • 2 BR,
                                    • 1 BA,
                                    • 1 HF BA,
                                    • Sleeps 4
                                      7 night minimum stay
                                      • 2 BR,
                                      • 1 BA,
                                      • Sleeps 6
                                        (12)
                                        • 1 BR,
                                        • 2 BA,
                                        • Sleeps 4
                                          (17)
                                          Book it Now!
                                          7 night minimum stay
                                          • 4 BR,
                                          • 3 BA,
                                          • Sleeps 10
                                            (9)
                                            $3,900 - $4,600
                                            per month
                                            30 night minimum stay
                                            • 3 BR,
                                            • 2 BA,
                                            • Sleeps 8
                                              (7)
                                              • 3 BR,
                                              • 2 BA,
                                              • Sleeps 7
                                                (3)
                                                28 night minimum stay
                                                • 5 BR,
                                                • 3 BA,
                                                • Sleeps 10
                                                  2 Reviews
                                                  3 night minimum stay
                                                  • Studio,
                                                  • 2 BA,
                                                  • Sleeps 8
                                                    28 night minimum stay
                                                    • 3 BR,
                                                    • 3 BA,
                                                    • Sleeps 6
                                                      $14,000
                                                      per month
                                                      28 night minimum stay
                                                      • 4 BR,
                                                      • 3 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 10
                                                        • 2 BR,
                                                        • 2 BA,
                                                        • Sleeps 4
                                                          (12)
                                                          28 night minimum stay
                                                          • 5 BR,
                                                          • 4 BA,
                                                          • Sleeps 12
                                                            7 - 30 night minimum stay
                                                            • 3 BR,
                                                            • 2 BA,
                                                            • Sleeps 6
                                                              (6)
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                                                              Recent Summerland Key Reviews

                                                              Just as Expected, Nothing Short of Perfect

                                                              5 of 5
                                                              This is the 3rd or 4th time I have stayed here and it never dissapoints. George always has the place ready and waiting for us and we have never had one issue during all the days we have stayed here. You cannot find a better located home for fishing and diving in a better location. The sunsets from even the back porch are remarkable. As always, the house is already booked for me for next year, so we will be back!
                                                              • Submitted: Sep 13, 2014
                                                              • Stayed: Aug 2014

                                                              We really really really loved your place.....

                                                              5 of 5
                                                              Thank you so much Mike. Wonderful place, clean and totally private.... We will come again in October.
                                                              • Submitted: Apr 3, 2014
                                                              • Stayed: Mar 2014

                                                              Great place for a big family!

                                                              4 of 5
                                                              Summerland Estate is a great place for a Keys vacation. You are close enough to Key West to hit the town and the night life but far enough away to get the quiet laid back Keys atmosphere. We had 10 in our party and had plenty of room for all of us. My three boys loved the "bachelor" pad downstairs. It was their own little slice of independence. The property is very well maintained and the manager and owner were very accommodating. We spent a lot of time on our boat and caught fish all week. Even caught some nice snapper right off the dock. My kids loved snorkeling off the dock and had some nurse sharks visit us almost every night. We have a 25 ft pontoon boat and the dock and deep water were perfect for even our bulky boat. The kids loved the pool and we enjoyed grilling out quite a bit in the evenings. Great relaxing vacation. Didn't get to use hot tub b/c of leak in it. But since it was summer in the Keys it wasn't an issue. I am sure the leak will be addressed as the rest of the house was well maintained. We will return again! ..
                                                              • Submitted: Jul 23, 2013
                                                              • Stayed: Jun 2013