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Florida Keys Vacation Home Rentals(1,423)

White Ibis Inn - Oceanview Estate. Summer Special!
    4 Bedrooms,
  • 3 Bathrooms
  • , Sleeps 14
Book it Now!
5 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 14
#951852
    16 Reviews
    Oceanfront Acre Heated Private Pool Sandy Area Dock 15 Min Key West
      3 Bedrooms,
    • 2 Bathrooms
    • , Sleeps 10
    7 night minimum stay
    • 3 BR,
    • 2 BA,
    • Sleeps 10
    #317093
      (52)
      Ocean Perch , Dock 80'Heated Pool Deep Channel Tennis 15 min Key West
        2 Bedrooms,
      • 2 Bathrooms
      • , Sleeps 6
      7 night minimum stay
      • 2 BR,
      • 2 BA,
      • Sleeps 6
      #315267
        (45)
        Marathon Luxury Waterfront Pool Home 75' Dock Fully Upgraded
          2 Bedrooms,
        • 2 Bathrooms
        • , Sleeps 6
        Book it Now!
        7 night minimum stay
        • 2 BR,
        • 2 BA,
        • Sleeps 6
        #902566
          (7)
          Private Luxury in Prestigious Casa Marina Neighborhood
            3 Bedrooms,
          • 3 Bathrooms
          • 1 Half Bath
          • , Sleeps 7
          28 night minimum stay
          • 3 BR,
          • 3 BA,
          • 1 HF BA,
          • Sleeps 7
          #298674
            (14)
            Luxury New Home with Pool/Dock on the Atlantic Near Key West
              2 Bedrooms,
            • 3 Bathrooms
            • , Sleeps 6
            3 night minimum stay
            • 2 BR,
            • 3 BA,
            • Sleeps 6
            #3020462
              (21)
              Location, Location, Location! Ocean View, Lagoon Beach Front
                3 Bedrooms,
              • 2 Bathrooms
              • , Sleeps 10
              3 night minimum stay
              • 3 BR,
              • 2 BA,
              • Sleeps 10
              #903627
                (15)
                'CONCH CASA GRANDE @ THE ANNEX': Enormous 7BR/7BA in Truman Annex...
                  7 Bedrooms,
                • 7 Bathrooms
                • , Sleeps 12
                7 night minimum stay
                • 7 BR,
                • 7 BA,
                • Sleeps 12
                #390171
                  (13)
                  HGTV Featured Home - Boaters Paradise! Waterfront Key West Home
                    3 Bedrooms,
                  • 2 Bathrooms
                  • , Sleeps 6
                  28 night minimum stay
                  • 3 BR,
                  • 2 BA,
                  • Sleeps 6
                  #277391
                    (33)
                    New Home in Gated Community with Oceanview, Pool & Dock! MM21!
                      2 Bedrooms,
                    • 3 Bathrooms
                    • , Sleeps 6
                    • 2 BR,
                    • 3 BA,
                    • Sleeps 6
                    #356519vb
                      (14)
                      'HIDDEN TREASURE @ CASA EAST': Luxurious 3BR 3BA Villa & Huge Pool near Beach...
                        3 Bedrooms,
                      • 3 Bathrooms
                      • , Sleeps 6
                      28 night minimum stay
                      • 3 BR,
                      • 3 BA,
                      • Sleeps 6
                      #390210
                        (8)
                        Waterfront Luxury Home with An Incredible View on a Full Acre, Free Secured WiFi
                          4 Bedrooms,
                        • 3 Bathrooms
                        • , Sleeps 8
                        7 night minimum stay
                        • 4 BR,
                        • 3 BA,
                        • Sleeps 8
                        #332253
                          (26)
                          Salida del Sol - Waterfront Key West Resort Style Home w/Pool & Beach
                            2 Bedrooms,
                          • 2 Bathrooms
                          • , Sleeps 6
                          Book it Now!
                          3 night minimum stay
                          • 2 BR,
                          • 2 BA,
                          • Sleeps 6
                          #3498085
                            (4)
                            'PUERTA CORALINA @ SOLARES HILL': Charming 2BR/3BA Cottage, 2 Master Suites...
                              2 Bedrooms,
                            • 3 Bathrooms
                            • , Sleeps 6
                            4 night minimum stay
                            • 2 BR,
                            • 3 BA,
                            • Sleeps 6
                            #904144
                              (24)
                              'CASA BLANCA 1888 @ WHITE': Historic 4BR/3BA Old Town Home + Very Large Pool....
                                4 Bedrooms,
                              • 3 Bathrooms
                              • , Sleeps 10
                              28 night minimum stay
                              • 4 BR,
                              • 3 BA,
                              • Sleeps 10
                              #390200
                                (13)
                                *$1395 wk 3/2.5 Lg Gulfside House with Dock & Cabana Club
                                  3 Bedrooms,
                                • 2 Bathrooms
                                • 1 Half Bath
                                • , Sleeps 8
                                7 night minimum stay
                                • 3 BR,
                                • 2 BA,
                                • 1 HF BA,
                                • Sleeps 8
                                #186293
                                  (49)
                                  Meagan's Beach House - Bayfront Home with spectacular Sunrises and Sunsets
                                    2 Bedrooms,
                                  • 2 Bathrooms
                                  • , Sleeps 6
                                  7 night minimum stay
                                  • 2 BR,
                                  • 2 BA,
                                  • Sleeps 6
                                  #265117
                                    (21)
                                    Affordable Key Largo Beach Cottage! Open water location
                                      2 Bedrooms,
                                    • 2 Bathrooms
                                    • , Sleeps 6
                                    3 night minimum stay
                                    • 2 BR,
                                    • 2 BA,
                                    • Sleeps 6
                                    #107982
                                      (6)
                                      'NOONA'S MANSION-by-the-SEA @ THE ANNEX' Sumptuous 7BR/5.5BA Home with Pool...
                                        7 Bedrooms,
                                      • 5 Bathrooms
                                      • 1 Half Bath
                                      • , Sleeps 14
                                      7 night minimum stay
                                      • 7 BR,
                                      • 5 BA,
                                      • 1 HF BA,
                                      • Sleeps 14
                                      #390202
                                        (25)
                                        'AVALYNN HOUSE @ THE ANNEX': Incredibly Spacious 5BR Home, Large Pool..
                                          5 Bedrooms,
                                        • 3 Bathrooms
                                        • 1 Half Bath
                                        • , Sleeps 12
                                        7 night minimum stay
                                        • 5 BR,
                                        • 3 BA,
                                        • 1 HF BA,
                                        • Sleeps 12
                                        #996261
                                          (10)
                                          'SOUTHERNMOST COMFORT @ CASA EAST': Stunning 4BR/4.5BA Home w/ Cottage & Pool...
                                            4 Bedrooms,
                                          • 4 Bathrooms
                                          • 1 Half Bath
                                          • , Sleeps 8
                                          28 night minimum stay
                                          • 4 BR,
                                          • 4 BA,
                                          • 1 HF BA,
                                          • Sleeps 8
                                          #990995
                                            (11)
                                            Bayfront and Beautiful, A Boater's Dream
                                              3 Bedrooms,
                                            • 3 Bathrooms
                                            • , Sleeps 8
                                            • 3 BR,
                                            • 3 BA,
                                            • Sleeps 8
                                            #191669
                                              8 Reviews
                                              Oceanfront Home Adjacent to Pennecamp Coral Reef State Park
                                                4 Bedrooms,
                                              • 3 Bathrooms
                                              • 1 Half Bath
                                              • , Sleeps 8
                                              • 4 BR,
                                              • 3 BA,
                                              • 1 HF BA,
                                              • Sleeps 8
                                              #312507
                                                6 Reviews
                                                'SOUTHERN STAR' @ THE SEAPORT' Renovated Historic 3BR/3BA Home with Pool...
                                                  3 Bedrooms,
                                                • 3 Bathrooms
                                                • , Sleeps 6
                                                28 night minimum stay
                                                • 3 BR,
                                                • 3 BA,
                                                • Sleeps 6
                                                #390182
                                                  (11)
                                                  Beach House with Open Water views! Dockage Included!
                                                    3 Bedrooms,
                                                  • 2 Bathrooms
                                                  • , Sleeps 10
                                                  3 night minimum stay
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • Sleeps 10
                                                  #314828
                                                    (10)
                                                    Sugarloaf Open Water Home With Beach, Dock and Swimming Canal
                                                      4 Bedrooms,
                                                    • 4 Bathrooms
                                                    • , Sleeps 8
                                                    Book it Now!
                                                    28 night minimum stay
                                                    • 4 BR,
                                                    • 4 BA,
                                                    • Sleeps 8
                                                    #436830vb
                                                      (5)
                                                      Bo's Tropical Get-a-Way in the beautiful sunny Florida Keys
                                                        2 Bedrooms,
                                                      • 2 Bathrooms
                                                      • , Sleeps 6
                                                      2 night minimum stay
                                                      • 2 BR,
                                                      • 2 BA,
                                                      • Sleeps 6
                                                      #234389
                                                        (7)
                                                        waterfront cottage w/Dock/2000 sq ft/clean/wifi/Cabana Club included
                                                          2 Bedrooms,
                                                        • 2 Bathrooms
                                                        • , Sleeps 7
                                                        • 2 BR,
                                                        • 2 BA,
                                                        • Sleeps 7
                                                        #301744
                                                          (29)
                                                          Waterfront Cottage - Beach and Dockage! Sunset Views!
                                                            2 Bedrooms,
                                                          • 1 Bathroom
                                                          • , Sleeps 4
                                                          3 night minimum stay
                                                          • 2 BR,
                                                          • 1 BA,
                                                          • Sleeps 4
                                                          #225990
                                                            (3)
                                                            Paradise for Rent in the Florida Keys!! Designer Vacation Home on Deep Water
                                                              3 Bedrooms,
                                                            • 2 Bathrooms
                                                            • , Sleeps 7
                                                            7 night minimum stay
                                                            • 3 BR,
                                                            • 2 BA,
                                                            • Sleeps 7
                                                            #330045
                                                              (19)