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Florida Keys with Air Conditioning(2,596)

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
    Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access
      2 Bedrooms,
    • 1 Bathroom
    • , Sleeps 4
    Book it Now!
    7 night minimum stay
    • 2 BR,
    • 1 BA,
    • Sleeps 4
    #244472
      (61)
      Ocean Breeze Suites-3 Bd, 3 Bath with loft Sleeps 10
        3 Bedrooms,
      • 3 Bathrooms
      • , Sleeps 10
      Book it Now!
      2 - 4 night minimum stay
      • 3 BR,
      • 3 BA,
      • Sleeps 10
      #367100
        (13)
        Charming Condo in Old Town Key West's Truman Annex
          1 Bedrooms,
        • 1 Bathroom
        • , Sleeps 2
        Book it Now!
        7 night minimum stay
        • 1 BR,
        • 1 BA,
        • Sleeps 2
        #290407
          (32)
          Key West Condo in Truman Annex with Whirlpool Tub, 2 Bikes, & Access to Pool!
            2 Bedrooms, Sleeps 4
          Book it Now!
          7 night minimum stay
          • 2 BR,
          • Sleeps 4
          #938538
            (19)
            Kawama Yacht Club- Oceanfront Private Beach - Sunsets!
              2 Bedrooms,
            • 2 Bathrooms
            • , Sleeps 8
            Book it Now!
            3 night minimum stay
            • 2 BR,
            • 2 BA,
            • Sleeps 8
            #404942vb
              (22)
              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)
                Charming, Romantic, Funky, Cozy, Unique, Beautiful, Island Charm, Beach, Ocean
                  1 Bedrooms,
                • 1 Bathroom
                • , Sleeps 2
                Book it Now!
                2 - 3 night minimum stay
                • 1 BR,
                • 1 BA,
                • Sleeps 2
                #972748
                  (8)
                  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)
                      Walk to the beach!
                        1 Bedrooms,
                      • 1 Bathroom
                      • , Sleeps 2
                      $2,146 - $2,884
                      per month
                      Book it Now!
                      28 night minimum stay
                      • 1 BR,
                      • 1 BA,
                      • Sleeps 2
                      #392129
                        (6)
                        STEPS FROM DUVAL! LUXURIOUS, SLEEPS 2-4, OLD TOWN
                          1 Bedrooms,
                        • 1 Bathroom
                        • , Sleeps 4
                        • 1 BR,
                        • 1 BA,
                        • Sleeps 4
                        #966039
                          (18)
                          '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)
                            'GULFSIDE VISTAS @ TRUMAN ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo...
                              2 Bedrooms,
                            • 2 Bathrooms
                            • 1 Half Bath
                            • , Sleeps 5
                            7 night minimum stay
                            • 2 BR,
                            • 2 BA,
                            • 1 HF BA,
                            • Sleeps 5
                            #904145
                              (21)
                              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)
                                Private Yacht 3 blocks from Duval Street & Sloppy Joe's
                                  3 Bedrooms, Sleeps 6
                                2 - 5 night minimum stay
                                • 3 BR,
                                • Sleeps 6
                                #390580vb
                                  (21)
                                  Waterfront, Boat Ramp, Pool, Tennis, Golf, Fishing, Diving
                                    1 Bedrooms,
                                  • 1 Bathroom
                                  • , Sleeps 4
                                  Book it Now!
                                  2 - 3 night minimum stay
                                  • 1 BR,
                                  • 1 BA,
                                  • Sleeps 4
                                  #910616
                                    (5)
                                    'WINDOWS ON THE GULF @ THE ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo..
                                      2 Bedrooms,
                                    • 2 Bathrooms
                                    • 1 Half Bath
                                    • , Sleeps 6
                                    7 night minimum stay
                                    • 2 BR,
                                    • 2 BA,
                                    • 1 HF BA,
                                    • Sleeps 6
                                    #390177
                                      (13)
                                      Oceanfront (Gulf) Condo, Fabulous Views, Heated Pool & Dock
                                        2 Bedrooms,
                                      • 2 Bathrooms
                                      • 1 Half Bath
                                      • , Sleeps 6
                                      7 night minimum stay
                                      • 2 BR,
                                      • 2 BA,
                                      • 1 HF BA,
                                      • Sleeps 6
                                      #113802
                                        (95)
                                        August Discounted! On the Ocean with Beach! Seaside Villa on Coco Plum
                                          2 Bedrooms,
                                        • 2 Bathrooms
                                        • , Sleeps 6
                                        7 night minimum stay
                                        • 2 BR,
                                        • 2 BA,
                                        • Sleeps 6
                                        #40371vb
                                          (36)
                                          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)
                                                Luxury Spacious Townhouse overlooking Pool w/ water view & 2 Bikes
                                                  1 Bedrooms,
                                                • 1 Bathroom
                                                • , Sleeps 4
                                                3 - 5 night minimum stay
                                                • 1 BR,
                                                • 1 BA,
                                                • Sleeps 4
                                                #3472045
                                                  (9)
                                                  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)
                                                    'SEA CAPTAIN'S HAVEN @ THE ANNEX': Immaculate Villa near Duval & Sunset Pier...
                                                      2 Bedrooms,
                                                    • 2 Bathrooms
                                                    • 1 Half Bath
                                                    • , Sleeps 6
                                                    7 night minimum stay
                                                    • 2 BR,
                                                    • 2 BA,
                                                    • 1 HF BA,
                                                    • Sleeps 6
                                                    #996654
                                                      (8)
                                                      Rare Penthouse 2 bed/2bath additional King in loft
                                                        2 Bedrooms,
                                                      • 2 Bathrooms
                                                      • , Sleeps 8
                                                      Book it Now!
                                                      2 - 4 night minimum stay
                                                      • 2 BR,
                                                      • 2 BA,
                                                      • Sleeps 8
                                                      #929000
                                                        (4)
                                                        Penthouse Condo Sunsets at Key Largo, Kawama Yacht Club Tower
                                                          2 Bedrooms,
                                                        • 2 Bathrooms
                                                        • , Sleeps 8
                                                        7 night minimum stay
                                                        • 2 BR,
                                                        • 2 BA,
                                                        • Sleeps 8
                                                        #233900
                                                          (33)
                                                          'EDEN @ THE ANNEX': 2BR/1.5BA Old Town Villa near Beach & Sunset Pier...
                                                            2 Bedrooms,
                                                          • 1 Bathroom
                                                          • 1 Half Bath
                                                          • , Sleeps 6
                                                          7 night minimum stay
                                                          • 2 BR,
                                                          • 1 BA,
                                                          • 1 HF BA,
                                                          • Sleeps 6
                                                          #390205
                                                            (7)
                                                            'CASA LOUISA @ UPPER DUVAL': Historic Conch Cottage & Pool 1/2 Block off Duval..
                                                              3 Bedrooms,
                                                            • 2 Bathrooms
                                                            • , Sleeps 8
                                                            4 night minimum stay
                                                            • 3 BR,
                                                            • 2 BA,
                                                            • Sleeps 8
                                                            #135603
                                                              (48)