Use filters to narrow your search results!

Summerland Key Vacation Rentals with Parking Included(50)

50 Results
Book it Now!
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
    (10)
    $5,200
    per month
    30 night minimum stay
    • 3 BR,
    • 2 BA,
    • Sleeps 8
      (5)
      7 night minimum stay
      • 5 BR,
      • 4 BA,
      • Sleeps 12
        (10)
        31 night minimum stay
        • 2 BR,
        • 2 BA,
        • Sleeps 8
          2 Reviews
          • 2 BR,
          • 2 BA,
          • Sleeps 8
            (14)
            • 3 BR,
            • 3 BA,
            • Sleeps 6
              1 Review
              28 night minimum stay
              • 2 BR,
              • 2 BA,
              • Sleeps 8
                30 night minimum stay
                • 2 BR,
                • 2 BA,
                • Sleeps 4
                  6 - 7 night minimum stay
                  • 2 BR,
                  • 2 BA,
                  • 1 HF BA,
                  • Sleeps 8
                    (34)
                    6 night minimum stay
                    • 3 BR,
                    • 2 BA,
                    • Sleeps 6
                      (3)
                      28 night minimum stay
                      • 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)
                              • 3 BR,
                              • 2 BA,
                              • Sleeps 10
                                (7)
                                34 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
                                      • 1 BR,
                                      • 2 BA,
                                      • Sleeps 4
                                        (16)
                                        7 night minimum stay
                                        • 2 BR,
                                        • 1 BA,
                                        • Sleeps 6
                                          (12)
                                          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)
                                              28 night minimum stay
                                              • 5 BR,
                                              • 3 BA,
                                              • Sleeps 10
                                                1 Review
                                                28 night minimum stay
                                                • 3 BR,
                                                • 3 BA,
                                                • Sleeps 6
                                                  3 night minimum stay
                                                  • Studio,
                                                  • 2 BA,
                                                  • Sleeps 8
                                                    • 2 BR,
                                                    • 2 BA,
                                                    • Sleeps 4
                                                      (12)
                                                      7 - 30 night minimum stay
                                                      • 3 BR,
                                                      • 2 BA,
                                                      • Sleeps 6
                                                        (6)
                                                        $8,000 - $11,000
                                                        per month
                                                        28 night minimum stay
                                                        • 3 BR,
                                                        • 3 BA,
                                                        • Sleeps 8
                                                          (5)
                                                          $3,868 - $4,568
                                                          per week
                                                          14 - 28 night minimum stay
                                                          • 5 BR,
                                                          • 4 BA,
                                                          • 1 HF BA,
                                                          • Sleeps 10
                                                            Advertisement
                                                             

                                                            Recent Summerland Key Reviews

                                                            FAMILY FUN FUN FUN!!!

                                                            5 of 5
                                                            Perfect family get away!! Kids played with kayaks, snorkeled in the canal, fished in the canal from morning till night. I brought my boat. Canal provides easy access to open water and bridges to fish from. My family caught about 60 fish during the week. We went to Key West and also took a charter to Looe Key to snorkel. Our week couldn't have been better.
                                                            • Submitted: Jun 25, 2014
                                                            • Stayed: Jun 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