A Quiet Paradise Is Possible in Summerland Key Rentals

Come experience the quiet and blue waters of the Florida Keys from Summerland Key rentals for your next tropical adventure. Much more serene than some of the more touristy Keys, this island is the ideal getaway when you simply want to relax and absorb your surroundings.

Live the Island Life in Summerland Key Rentals


Live among the tropical birds and plants by staying in Summerland Key condos, and have the added advantage of being within walking distance to your favorite watering hole or seaside restaurant. Fresh seafood, warm weather and plenty of sunshine are virtually guaranteed to renew and recharge you when you stay in Summerland Key villas.

Relax on the Beach near Summerland Key Condos


Find your Summerland Key rentals on the beach so you can easily step out for a morning jog or evening stroll in the moonlight. Perhaps you simply want to nap or read in the sun while the kids play in the sand; Summerland Key condos let you do as much or as little as you like, providing comfortable air conditioning and private quarters any time of day.

Reserve your Summerland Key villas and enjoy simply forgetting about the world for at least a few days; a stop at the local market upon arrival will allow you to enjoy the use of your fully-equipped kitchen without interacting with others for a time.

Choose Summerland Key Villas for Your Group Outing


Family vacations are a great reason for staying in Summerland Key rentals, as everyone can have their own bedrooms and even bathrooms to avoid any feeling of crowding. Honeymooners also love the seclusion of Summerland Key villas located in the midst of the local rainforests and access to private beaches. Don’t forget that Summerland Key condos are also great for a unique family reunion, destination wedding on the beach, extended winter stay, and even working vacations or business retreats.

Expand your search for Florida vacation rentals to include Miami vacation rentals and Ft. Lauderdale rentals in South Florida, Destin vacation rentals and Siesta Key rentals on the Gulf Coast, or Orlando vacation home rentals near Disney.


Use filters to narrow your search results!

Summerland Key: Houses, Estates & More(55)

55 Results
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
#436601vb
(8)
6 night minimum stay
  • 4 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 10
#3503655
(3)
    $5,200
    per month
    30 night minimum stay
    • 3 BR,
    • 2 BA,
    • Sleeps 8
    #493005vb
    (5)
      7 night minimum stay
      • 5 BR,
      • 4 BA,
      • Sleeps 12
      #271701
      (10)
        31 night minimum stay
        • 2 BR,
        • 2 BA,
        • Sleeps 8
        #475762vb
        2 Reviews
          • 2 BR,
          • 2 BA,
          • Sleeps 8
          #155489vb
          (14)
            • 3 BR,
            • 3 BA,
            • Sleeps 6
            #196245vb
            1 Review
              $350
              per night
              2 night minimum stay
              • 2 BR,
              • 2 BA,
              • Sleeps 6
              #169213
              (9)
                6 - 7 night minimum stay
                • 2 BR,
                • 2 BA,
                • 1 HF BA,
                • Sleeps 8
                #369579
                (32)
                  6 night minimum stay
                  • 3 BR,
                  • 2 BA,
                  • Sleeps 6
                  #211102
                  (3)
                    28 night minimum stay
                    • 4 BR,
                    • 4 BA,
                    • Sleeps 8
                    #3689979
                    28 night minimum stay
                    • 4 BR,
                    • 2 BA,
                    • Sleeps 12
                    #3013471
                      $17,733
                      per month
                      28 - 30 night minimum stay
                      • 5 BR,
                      • 3 BA,
                      • 1 HF BA,
                      • Sleeps 10
                      #3732809
                      2 Reviews
                        $8,820
                        per month
                        28 night minimum stay
                        • 3 BR,
                        • 3 BA,
                        • Sleeps 6
                        #3490836
                          • 7 BR,
                          • 5 BA,
                          • Sleeps 14
                          #327552
                          (11)
                            28 night minimum stay
                            • 3 BR,
                            • 2 BA,
                            • Sleeps 8
                            #3671087
                              • 4 BR,
                              • 3 BA,
                              • Sleeps 10
                              #309804
                              (7)
                                • 4 BR,
                                • 4 BA,
                                • Sleeps 8
                                #3552534
                                  • 3 BR,
                                  • 2 BA,
                                  • Sleeps 7
                                  #374931vb
                                  (5)
                                    36 more choices from the HomeAway Network
                                    $3,500
                                    per month
                                    28 night minimum stay
                                    • 3 BR,
                                    • 2 BA,
                                    • Sleeps 6
                                    #442915vb
                                    1 Review
                                    $1,400 - $1,575
                                    per week
                                    14 night minimum stay
                                    • 2 BR,
                                    • 1 BA,
                                    • 1 HF BA,
                                    • Sleeps 4
                                    #509144vb
                                    • 1 BR,
                                    • 2 BA,
                                    • Sleeps 4
                                    #106235vb
                                    (14)
                                      7 night minimum stay
                                      • 2 BR,
                                      • 1 BA,
                                      • Sleeps 6
                                      #443256vb
                                      (10)
                                        28 night minimum stay
                                        • 5 BR,
                                        • 3 BA,
                                        • Sleeps 12
                                        #451644vb
                                        1 Review
                                          28 night minimum stay
                                          • 2 BR,
                                          • 2 BA,
                                          • Sleeps 8
                                          #499078vb
                                            28 night minimum stay
                                            • 3 BR,
                                            • 3 BA,
                                            • Sleeps 8
                                            #507444vb
                                              28 night minimum stay
                                              • 2 BR,
                                              • 1 BA,
                                              • Sleeps 4
                                              #580052vb
                                                28 night minimum stay
                                                • 3 BR,
                                                • 2 BA,
                                                • Sleeps 6
                                                #396273vb
                                                1 Review
                                                  • 2 BR,
                                                  • 2 BA,
                                                  • Sleeps 4
                                                  #376262vb
                                                  (11)
                                                    28 night minimum stay
                                                    • 1 BR,
                                                    • 1 BA,
                                                    • Sleeps 4
                                                    #364224vb
                                                    (20)
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