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Summerland Key Pet Friendly Vacation Rentals(24)

24 Results
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)
        Book it Now!
        7 night minimum stay
        • 3 BR,
        • 3 BA,
        • Sleeps 6
          2 Reviews
          30 night minimum stay
          • 2 BR,
          • 2 BA,
          • Sleeps 4
            28 night minimum stay
            • 2 BR,
            • 2 BA,
            • Sleeps 8
              6 night minimum stay
              • 3 BR,
              • 2 BA,
              • Sleeps 6
                (3)
                Book it Now!
                28 night minimum stay
                • 4 BR,
                • 4 BA,
                • Sleeps 8
                  • 4 BR,
                  • 2 BA,
                  • Sleeps 12
                    28 night minimum stay
                    • 3 BR,
                    • 2 BA,
                    • Sleeps 8
                      $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
                            • 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
                                        $16,575
                                        per month
                                        14 - 28 night minimum stay
                                        • 5 BR,
                                        • 4 BA,
                                        • 1 HF BA,
                                        • Sleeps 10
                                          • 3 BR,
                                          • 1 BA,
                                          • Sleeps 4
                                            • 2 BR,
                                            • 2 BA,
                                            • Sleeps 8
                                              1 Review
                                              • 3 BR,
                                              • 3 BA,
                                              • Sleeps 8
                                                (5)
                                                • 2 BR,
                                                • 2 BA,
                                                • Sleeps 8
                                                  (5)
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                                                  Recent Summerland Key Reviews

                                                  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

                                                  Fishing in the Keys

                                                  5 of 5
                                                  This place was absolutely perfect. Everything in the place worked great, especially the A/C. The outdoor BBQ was perfect, as were the rest of the amenities. I would stay here again in a heartbeat.
                                                  • Submitted: May 28, 2013
                                                  • Stayed: May 2013