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Key West Long Term Rentals(143)

Full Month Discounts Now Available in Truman Annex, Key West
    2 Bedrooms,
  • 2 Bathrooms
  • 1 Half Bath
  • , Sleeps 5
7 night Minimum Stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 5
#982960
    (12)
    'OLD TOWN OASIS @ TRUMAN ANNEX': Luxurious 2BR/2BA Condo + Oceanside Pool...
      2 Bedrooms,
    • 2 Bathrooms
    • , Sleeps 6
    7 night Minimum Stay
    • 2 BR,
    • 2 BA,
    • Sleeps 6
    #390175
      (23)
      Key West Boat & Breakfast, Reef Sailing Trips, ASA sailing coming soon
        2 Bedrooms,
      • 2 Bathrooms
      • , Sleeps 4
      2 - 3 night Minimum Stay
      • 2 BR,
      • 2 BA,
      • Sleeps 4
      #229193
        (19)
        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
          (32)
          Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access
            2 Bedrooms,
          • 1 Bathroom
          • , Sleeps 4
          • 2 BR,
          • 1 BA,
          • Sleeps 4
          #244472
            (61)
            Charming Condo in Old Town Key West's Truman Annex
              1 Bedrooms,
            • 1 Bathroom
            • , Sleeps 2
            • 1 BR,
            • 1 BA,
            • Sleeps 2
            #290407
              (31)
              Southernmost Retreat: 1 Block from Duval in Old Town.
                3 Bedrooms,
              • 2 Bathrooms
              • , Sleeps 6
              • 3 BR,
              • 2 BA,
              • Sleeps 6
              #959155
                (9)
                'SUNSET POINT @ SUNSET MARINA': Immaculate 3BR/2BA Waterfront Condo...
                  3 Bedrooms,
                • 2 Bathrooms
                • , Sleeps 8
                28 night Minimum Stay
                • 3 BR,
                • 2 BA,
                • Sleeps 8
                #3549915
                  'VILLA PARADISO @ CASA MARINA': Airy & Spacious Villa + Large Pool..
                    2 Bedrooms,
                  • 2 Bathrooms
                  • , Sleeps 6
                  28 night Minimum Stay
                  • 2 BR,
                  • 2 BA,
                  • Sleeps 6
                  #915976
                    (3)
                    'TROPICAL JEWEL @ THE SEAPORT': 2BR/2BA Lovely Old Town Cottage + Pool...
                      3 Bedrooms,
                    • 2 Bathrooms
                    • , Sleeps 7
                    28 night Minimum Stay
                    • 3 BR,
                    • 2 BA,
                    • Sleeps 7
                    #390191
                      1 Review
                      'PORTSIDE MANSION @ THE SEAPORT': Lush 6BR/7BA 3-Building Home + Large Pool.....
                        6 Bedrooms,
                      • 2 Bathrooms
                      • 1 Half Bath
                      • , Sleeps 12
                      28 night Minimum Stay
                      • 6 BR,
                      • 2 BA,
                      • 1 HF BA,
                      • Sleeps 12
                      #390194
                        (7)
                        Ocean Retreat
                          3 Bedrooms,
                        • 2 Bathrooms
                        • 1 Half Bath
                        • , Sleeps 5
                        $2,900 - $4,900
                        per week
                        7 night Minimum Stay
                        • 3 BR,
                        • 2 BA,
                        • 1 HF BA,
                        • Sleeps 5
                        #327107
                          (3)
                          'OCTOPUS'S GARDEN @ CORAL HAMMOCK': 3BR/3BA Spacious Home w Pool & Gym
                            3 Bedrooms,
                          • 3 Bathrooms
                          • , Sleeps 8
                          7 night Minimum Stay
                          • 3 BR,
                          • 3 BA,
                          • Sleeps 8
                          #3482727
                            2 Reviews
                            Real World MTV House---Not Just a House Your Own Private Resort
                              10 Bedrooms,
                            • 5 Bathrooms
                            • 1 Half Bath
                            • , Sleeps 24
                            4 night Minimum Stay
                            • 10 BR,
                            • 5 BA,
                            • 1 HF BA,
                            • Sleeps 24
                            #326563
                              (14)
                              'WATERFRONT RETREAT @ THE FLORIDA BAY': 3BR/3BA Canal Front Home...
                                3 Bedrooms,
                              • 3 Bathrooms
                              • , Sleeps 8
                              28 night Minimum Stay
                              • 3 BR,
                              • 3 BA,
                              • Sleeps 8
                              #3469621
                                'PARADISE PERFECTED @ SMATHERS BEACH': Handsome Beach House + Pool...
                                  3 Bedrooms,
                                • 2 Bathrooms
                                • , Sleeps 8
                                28 night Minimum Stay
                                • 3 BR,
                                • 2 BA,
                                • Sleeps 8
                                #3545074
                                  'CASA FELIZ @ THE SEAPORT': Lushly Furnished 3BR/3.5BA Private Home + Pool...
                                    3 Bedrooms,
                                  • 3 Bathrooms
                                  • , Sleeps 8
                                  28 night Minimum Stay
                                  • 3 BR,
                                  • 3 BA,
                                  • Sleeps 8
                                  #390195
                                    (5)
                                    'CASA PLUMERIA @ OLD TOWN SOUTH': 4BR/3.5BA Home & Guest Cottage + Pool...
                                      4 Bedrooms,
                                    • 3 Bathrooms
                                    • 1 Half Bath
                                    • , Sleeps 10
                                    28 night Minimum Stay
                                    • 4 BR,
                                    • 3 BA,
                                    • 1 HF BA,
                                    • Sleeps 10
                                    #390189
                                      (4)
                                      Key West ocean view 3 bedroom Truman Annex vacation condo
                                        3 Bedrooms,
                                      • 3 Bathrooms
                                      • , Sleeps 6
                                      7 night Minimum Stay
                                      • 3 BR,
                                      • 3 BA,
                                      • Sleeps 6
                                      #209190
                                        1 Review
                                        Luxury on Garrison Bight: 3 BR/3.5 BA Waterfront Home Sleeps 8
                                          3 Bedrooms,
                                        • 3 Bathrooms
                                        • 1 Half Bath
                                        • , Sleeps 8
                                        3 - 6 night Minimum Stay
                                        • 3 BR,
                                        • 3 BA,
                                        • 1 HF BA,
                                        • Sleeps 8
                                        #3475121
                                          1 Review
                                          Tiki Beach Too, Charming Townhome, Old Town, Pool Access, great porch!
                                            2 Bedrooms,
                                          • 1 Bathroom
                                          • , Sleeps 6
                                          7 night Minimum Stay
                                          • 2 BR,
                                          • 1 BA,
                                          • Sleeps 6
                                          #3539485
                                            'CASA, SUITE CASA @ CASA MARINA': Lavish New Home W/ 4 Suites + Pool...
                                              4 Bedrooms,
                                            • 5 Bathrooms
                                            • , Sleeps 10
                                            28 night Minimum Stay
                                            • 4 BR,
                                            • 5 BA,
                                            • Sleeps 10
                                            #3485544
                                              2 Reviews
                                              Key West vacation townhouse rental in the Truman Annex
                                                2 Bedrooms,
                                              • 2 Bathrooms
                                              • 1 Half Bath
                                              • , Sleeps 6
                                              7 night Minimum Stay
                                              • 2 BR,
                                              • 2 BA,
                                              • 1 HF BA,
                                              • Sleeps 6
                                              #209088
                                                (5)
                                                6 bedrooms w/ Pool, Hot Tub, Parking & Huge Roof Deck on Duval Street
                                                  6 Bedrooms,
                                                • 7 Bathrooms
                                                • , Sleeps 14
                                                • 6 BR,
                                                • 7 BA,
                                                • Sleeps 14
                                                #228157
                                                  (4)
                                                  Luxurious Garden Home Paradise with Pool in Midtown Key West
                                                    2 Bedrooms,
                                                  • 1 Bathroom
                                                  • , Sleeps 6
                                                  • 2 BR,
                                                  • 1 BA,
                                                  • Sleeps 6
                                                  #388391
                                                    (4)
                                                    High End Luxury House on Old Town Lane, Pool--Free Wireless Monthly Rentals Only
                                                      2 Bedrooms,
                                                    • 2 Bathrooms
                                                    • , Sleeps 4
                                                    • 2 BR,
                                                    • 2 BA,
                                                    • Sleeps 4
                                                    #159918
                                                      2 Reviews
                                                      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
                                                        (14)
                                                        'SUZY'S PARROT PERCH @ SOUTHERNMOST': Cozy 2BR/1BA Suite Near Duval...
                                                          2 Bedrooms,
                                                        • 1 Bathroom
                                                        • , Sleeps 4
                                                        4 night Minimum Stay
                                                        • 2 BR,
                                                        • 1 BA,
                                                        • Sleeps 4
                                                        #3469827
                                                          (12)
                                                          Coral Hammock - Beautiful Poolside Home (28)
                                                            3 Bedrooms,
                                                          • 3 Bathrooms
                                                          • , Sleeps 6
                                                          3 night Minimum Stay
                                                          • 3 BR,
                                                          • 3 BA,
                                                          • Sleeps 6
                                                          #994631
                                                            (9)
                                                            'SWEET CAROLINE'S SANCTUARY @ THE SEAPORT': Cozy 1BR/1BA Condo + Pool, Spa...
                                                              1 Bedrooms,
                                                            • 1 Bathroom
                                                            • , Sleeps 4
                                                            28 night Minimum Stay
                                                            • 1 BR,
                                                            • 1 BA,
                                                            • Sleeps 4
                                                            #390174
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