Dog Friendly Vacation Rentals in Key West - FlipKey

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

Filtering by: Pets allowed

195 pet friendly house rentals in Key West

(3) Very Good 

    16

    Conch Haven Old Town 1/1 MONTHLY Rental

    Florida Keys / Key West

    Key West apartment

    1 4 min stay varies

    • 1 bedroom
    • sleeps 4
    • min stay varies
    • Beach / lakeside relaxation
    • Child Friendly
    • Car not necessary

    Price per night from

    $93

    Responds fast!
    avg. 3 hours 28 minutes

    Price per night from

    $93

    (18) Very Good 

      27

      Houseboat Trawler MV Coconuts: Once in a Lifetime Vacation With Pool Access

      Florida Keys / Key West

      Key West house

      3 8 2 nights min

      • 3 bedrooms
      • sleeps 8
      • 2 nights min
      • Swimming pool
      • Ask about children
      • Air conditioning
      “Nice alternatif for hotel” We were on the boat with only 2 people, so plenty of place ! We liked the marina and the boat very well. Something completely different than an hotelroom ... We had perfect weather so we used the different terraces on the b

      Price per night from

      $182

      Price per night from

      $182

        14

        Key West Island Vacation

        Florida Keys / Key West

        Key West house

        2 6 30 nights min

        • 2 bedrooms
        • sleeps 6
        • 30 nights min
        • Child Friendly
        • Air conditioning
        • Pet Friendly

        Price per night from

        $477

        Price per night from

        $477

          13

          Private and Immaculate 2 Bedroom Home with Private Fenced Yard

          Florida Keys / Key West

          Key West house

          2 4 28 nights min

          • 2 bedrooms
          • sleeps 4
          • 28 nights min
          • Nearest beach 2 mi
          • Child Friendly
          • Air conditioning

          Price per night from

          $137

          Price per night from

          $137

            19

            A Touch Of Havana In Key West

            Florida Keys / Key West

            Key West condo

            2 4 7 nights min

            • 2 bedrooms
            • sleeps 4
            • 7 nights min
            • Nearest beach 0.5 mi
            • Swimming pool
            • Child Friendly

            Price per night from

            $352

            Responds fast!
            avg. 2 hours 18 minutes

            Price per night from

            $352

              24

              Hidden Treasure

              Florida Keys / Key West

              Key West apartment

              2 4 min stay varies

              • 2 bedrooms
              • sleeps 4
              • min stay varies
              • Swimming pool
              • Child Friendly
              • Pet Friendly

              Price per night from

              $78

              Price per night from

              $78

              (3) Excellent 

                25

                Quilted Giraffe

                Florida Keys / Key West

                Key West house

                2 4 min stay varies

                • 2 bedrooms
                • sleeps 4
                • min stay varies
                • Swimming pool
                • Child Friendly
                • Air conditioning

                Price per night from

                $400

                Price per night from

                $400

                (2) Excellent 

                  51

                  Welcome Aboard! Relax, unwind, enjoy the water! in key west

                  Florida Keys / Key West

                  Key West yacht

                  4 6 2 nights min

                  • 4 bedrooms
                  • sleeps 6
                  • 2 nights min
                  • Nearest beach 1 mi
                  • Swimming pool
                  • Air conditioning

                  Price per night from

                  $283

                  Price per night from

                  $283

                    24

                    First Breath

                    Florida Keys / Key West

                    Key West house

                    3 6 min stay varies

                    • 3 bedrooms
                    • sleeps 6
                    • min stay varies
                    • Swimming pool
                    • Child Friendly
                    • Pet Friendly

                    Price per night from

                    $107

                    Price per night from

                    $107

                      24

                      Green Orchid

                      Florida Keys / Key West

                      Key West house

                      2 4 min stay varies

                      • 2 bedrooms
                      • sleeps 4
                      • min stay varies
                      • Child Friendly
                      • Pet Friendly

                      Price per night from

                      $93

                      Price per night from

                      $93

                        24

                        Kokomo

                        Florida Keys / Key West

                        Key West house

                        2 4 min stay varies

                        • 2 bedrooms
                        • sleeps 4
                        • min stay varies
                        • Swimming pool
                        • Child Friendly
                        • Pet Friendly

                        Price per night from

                        $73

                        Price per night from

                        $73

                          24

                          Coconut Cottage

                          Florida Keys / Key West

                          Key West house

                          1 2 min stay varies

                          • 1 bedroom
                          • sleeps 2
                          • min stay varies
                          • Swimming pool
                          • Child Friendly
                          • Pet Friendly

                          Price per night from

                          $91

                          Price per night from

                          $91

                            29

                            Key West Gulf front Home with private dock and pool.

                            Florida Keys / Key West

                            Key West house

                            3 6 28 nights min

                            • 3 bedrooms
                            • sleeps 6
                            • 28 nights min
                            • Nearest beach 2 mi
                            • Swimming pool
                            • Child Friendly

                            Price per night from

                            $324

                            Responds fast!
                            avg. 3 hours 57 minutes

                            Price per night from

                            $324

                            (4) Excellent 

                              24

                              Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes

                              Florida Keys / Key West

                              Key West townhouse

                              2 6 7 nights min

                              • 2 bedrooms
                              • sleeps 6
                              • 7 nights min
                              • Swimming pool
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $357

                              Responds fast!
                              avg. 3 hours 11 minutes

                              Price per night from

                              $357

                              (6) Excellent 

                                25

                                Coral Casita

                                Florida Keys / Key West

                                Key West house

                                3 8 min stay varies

                                • 3 bedrooms
                                • sleeps 8
                                • min stay varies
                                • Swimming pool
                                • Child Friendly
                                • Pet Friendly
                                “Celebrating 50 Years” My family rented this house for a girls week getaway to celebrate my sisters 50th birthday. The house was wonderful! The bedrooms were roomy, the balcony's on every level were absolutely fabulous! WE would absolutely recommend

                                Price per night from

                                $210

                                Price per night from

                                $210

                                (9) Excellent 

                                  32

                                  New Listing Family Friendly

                                  Florida Keys / Key West

                                  Key West townhouse

                                  3 6 3 nights min

                                  • 3 bedrooms
                                  • sleeps 6
                                  • 3 nights min
                                  • Child Friendly
                                  • Air conditioning
                                  • Pet Friendly

                                  Price per night from

                                  $367

                                  Responds fast!
                                  avg. 43 minutes

                                  Price per night from

                                  $367

                                    24

                                    A Little Slice Of Paradise

                                    Florida Keys / Key West

                                    Key West house

                                    2 6 min stay varies

                                    • 2 bedrooms
                                    • sleeps 6
                                    • min stay varies
                                    • Swimming pool
                                    • Child Friendly
                                    • Pet Friendly

                                    Price per night from

                                    $73

                                    Price per night from

                                    $73

                                    (7) Average 

                                      22

                                      Key Lime Pie

                                      Florida Keys / Key West

                                      Key West house

                                      2 4 min stay varies

                                      • 2 bedrooms
                                      • sleeps 4
                                      • min stay varies
                                      • Swimming pool
                                      • Child Friendly
                                      • Pet Friendly
                                      “Loved Off Season Key West” Spent a month in this very secluded house within walking distance of everything, including the marina, Duval Street and my favorite Watering Hole, Finnegan's Irish Wake pub. Renting in October, the off season, meant I go

                                      Price per night from

                                      $87

                                      Price per night from

                                      $87

                                      (8) Very Good 

                                        24

                                        Perfect Pineapple

                                        Florida Keys / Key West

                                        Key West house

                                        2 4 min stay varies

                                        • 2 bedrooms
                                        • sleeps 4
                                        • min stay varies
                                        • Swimming pool
                                        • Child Friendly
                                        • Pet Friendly
                                        “Kudos to Owner” The owners updated many things such as new bathroom tile, area rugs, washer and dryer area as well as painting. Still needed are more dinner and salad plates as it is necessary to run the dishwasher almost every day. The timer system f

                                        Price per night from

                                        $99

                                        Price per night from

                                        $99

                                        (4) Very Good 

                                          21

                                          Duval On The Square

                                          Florida Keys / Key West

                                          Key West house

                                          2 6 min stay varies

                                          • 2 bedrooms
                                          • sleeps 6
                                          • min stay varies
                                          • Swimming pool
                                          • Child Friendly
                                          • Pet Friendly
                                          “A really good place to stay” Duval Square is a very good location. Crowd noise is not a problem. However the parrots from the New York restaurant below can get annoying. The inside of the apartment is nicely done. The balcony's overlooking the squa

                                          Price per night from

                                          $100

                                          Price per night from

                                          $100

                                            24

                                            Old Town Eyebrow:Luxurious/Private Home

                                            Florida Keys / Key West

                                            Key West house

                                            3 8 30 nights min

                                            • 3 bedrooms
                                            • sleeps 8
                                            • 30 nights min
                                            • Child Friendly
                                            • Air conditioning
                                            • Pet Friendly

                                            Price per night from

                                            $488

                                            Price per night from

                                            $488

                                            (54) Excellent 

                                              25

                                              Poinciana House

                                              Florida Keys / Key West

                                              Key West house

                                              1 4 min stay varies

                                              • 1 bedroom
                                              • sleeps 4
                                              • min stay varies
                                              • Swimming pool
                                              • Child Friendly
                                              • Air conditioning
                                              “Awesome” The house was just as Historic Hideaways pictured and described...beautiful. The house was very clean, a pool service came twice a week to clean the pool and Tim, (agent) was very informative and helpful. Everything was supplied from towels t

                                              Price per night from

                                              $350

                                              Price per night from

                                              $350

                                              (24) Very Good 

                                                25

                                                The Prive

                                                Florida Keys / Key West

                                                Key West house

                                                2 4 min stay varies

                                                • 2 bedrooms
                                                • sleeps 4
                                                • min stay varies
                                                • Swimming pool
                                                • Child Friendly
                                                • Air conditioning
                                                “What a wonderful place to forget the long cold winter and renew” The house was beautiful . The neighborhood was quiet and peaceful. It was everything we had hoped it would be. Everything you could possibly need in a house was there. The house was spot

                                                Price per night from

                                                $250

                                                Price per night from

                                                $250

                                                (8) Excellent 

                                                  69

                                                  LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH

                                                  Florida Keys / Key West

                                                  Key West apartment

                                                  1 4 min stay varies

                                                  • 1 bedroom
                                                  • sleeps 4
                                                  • min stay varies
                                                  • Beach / lakeside relaxation
                                                  • Swimming pool
                                                  • Child Friendly
                                                  “Wonderful Experience” Beautiful decor! Perfect location - just off the beaten path but out of the hustle and bustle. Convenient to everything we wanted to do! I whole heartedly recommend this condo for a couple. Also would work nicely for three people

                                                  Price per night from

                                                  $181

                                                  Responds fast!
                                                  avg. 2 hours 36 minutes

                                                  Price per night from

                                                  $181

                                                  (2) Very Good 

                                                    24

                                                    Ibis

                                                    Florida Keys / Key West

                                                    Key West house

                                                    1 2 min stay varies

                                                    • 1 bedroom
                                                    • sleeps 2
                                                    • min stay varies
                                                    • Swimming pool
                                                    • Child Friendly
                                                    • Pet Friendly

                                                    Price per night from

                                                    $75

                                                    Price per night from

                                                    $75

                                                      24

                                                      tropical Casita

                                                      Florida Keys / Key West

                                                      Key West house

                                                      1 2 min stay varies

                                                      • 1 bedroom
                                                      • sleeps 2
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Child Friendly
                                                      • Pet Friendly

                                                      Price per night from

                                                      $100

                                                      Price per night from

                                                      $100

                                                      (56) Very Good 

                                                        24

                                                        Amelia Home

                                                        Florida Keys / Key West

                                                        Key West house

                                                        2 6 min stay varies

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • min stay varies
                                                        • Swimming pool
                                                        • Child Friendly
                                                        • Air conditioning
                                                        “Perfect” We loved this house! It was the perfect little getaway. It was in a great location, very convenient to everything. The house was beautiful with very nice decorating inside to the beautiful lush garden outside. If we visit Key West again,

                                                        Price per night from

                                                        $300

                                                        Price per night from

                                                        $300

                                                        (59) Very Good 

                                                          24

                                                          Tropical Dreaming

                                                          Florida Keys / Key West

                                                          Key West house

                                                          2 6 min stay varies

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Air conditioning
                                                          “Oasis in busy Key West” We have stayed at Tropical Dreaming several years in a row. It is a lovely setting a couple of blocks off Duval so it is its own oasis.

                                                          Price per night from

                                                          $350

                                                          Price per night from

                                                          $350

                                                          (17) Excellent 

                                                            19

                                                            A Touch of Bermuda in Key West

                                                            Florida Keys / Key West

                                                            Key West house

                                                            2 6 7 nights min

                                                            • 2 bedrooms
                                                            • sleeps 6
                                                            • 7 nights min
                                                            • Beach / lakeside relaxation
                                                            • Nearest beach 0.5 mi
                                                            • Swimming pool
                                                            “Lovely Home and Great Location for our Key West Vacation” We had a great time at The Touch of Bermuda Cottage on Truman annex. We knew this was a good location from previous trips, and we also knew we wanted to find an individual home with all the ame

                                                            Price per night from

                                                            $349

                                                            Responds fast!
                                                            avg. 2 hours 18 minutes

                                                            Price per night from

                                                            $349

                                                            (52) Very Good 

                                                              25

                                                              Key West Ginger Whole House

                                                              Florida Keys / Key West

                                                              Key West cottage

                                                              2 6 min stay varies

                                                              • 2 bedrooms
                                                              • sleeps 6
                                                              • min stay varies
                                                              • Child Friendly
                                                              • Air conditioning
                                                              • Pet Friendly
                                                              “Ginger House = Perfect Getaway” Rented this property for Labor Day Weekend for a Bachelor Party and the location was ideal. House was clean and in good condition and it was perfect. It's not large, so keep your party relatively small but I was impress

                                                              Price per night from

                                                              $230

                                                              Price per night from

                                                              $230

                                                              (1) Excellent 

                                                                24

                                                                Here Tomorrow

                                                                Florida Keys / Key West

                                                                Key West house

                                                                3 6 min stay varies

                                                                • 3 bedrooms
                                                                • sleeps 6
                                                                • min stay varies
                                                                • Swimming pool
                                                                • Child Friendly
                                                                • Pet Friendly
                                                                “Exceeded our expectations” We loved this house! Super location - just one block off Duval - and also near to the beach; we went to the Southernmost beach a lot. We thought that the house is bigger then it looks in the photographs. We were expecting

                                                                Price per night from

                                                                $117

                                                                Price per night from

                                                                $117

                                                                (29) Very Good 

                                                                  24

                                                                  Paradise Place

                                                                  Florida Keys / Key West

                                                                  Key West apartment

                                                                  1 4 min stay varies

                                                                  • 1 bedroom
                                                                  • sleeps 4
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Air conditioning
                                                                  “The Condo was all we had hoped it would be and more.” The condo was clean, good size, and fully stocked (i.e. linens, towels, kitchen equipment & necessary supplies. Oh yes, and two large Tv's (we like to watch the news). Wish it was located a little

                                                                  Price per night from

                                                                  $140

                                                                  Price per night from

                                                                  $140

                                                                  (50) Very Good 

                                                                    22

                                                                    Duval Street Suite

                                                                    Florida Keys / Key West

                                                                    Key West apartment

                                                                    2 6 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 6
                                                                    • min stay varies
                                                                    • Child Friendly
                                                                    • Air conditioning
                                                                    • Pet Friendly
                                                                    “Bachelorette Paradise” I spent the weekend in Key West with a group of girlfriends for my bachelorette party. We could not be more pleased with the Duval Street Suite. The apartment had a beautiful wrap around porch, great for people watching. The kit

                                                                    Price per night from

                                                                    $275

                                                                    Price per night from

                                                                    $275

                                                                      10

                                                                      Atlantis Dream Escape

                                                                      Florida Keys / Key West

                                                                      Key West house

                                                                      3 8 30 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 8
                                                                      • 30 nights min
                                                                      • Child Friendly
                                                                      • Pet Friendly

                                                                      Price per night from

                                                                      $322

                                                                      Price per night from

                                                                      $322

                                                                      (7) Very Good 

                                                                        16

                                                                        The Tree House Old Town 2 Bedroom MONTHLY Rental

                                                                        Florida Keys / Key West

                                                                        Key West house

                                                                        2 7 30 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 7
                                                                        • 30 nights min
                                                                        • Ask about children
                                                                        • Car not necessary
                                                                        • Air conditioning
                                                                        “Wonderful” Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job an

                                                                        Price per night from

                                                                        $100

                                                                        Responds fast!
                                                                        avg. 3 hours 28 minutes

                                                                        Price per night from

                                                                        $100

                                                                          17

                                                                          Ambrosia - OLD TOWN/HISTORIC SEAPORT, large POOL, wrap around porch, washer/dry

                                                                          Florida Keys / Key West

                                                                          Key West condo

                                                                          1 4 28 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 4
                                                                          • 28 nights min
                                                                          • Swimming pool
                                                                          • Air conditioning
                                                                          • Pet Friendly

                                                                          Price per night from

                                                                          $132

                                                                          Price per night from

                                                                          $132

                                                                            8

                                                                            Beautiful Mango House

                                                                            Florida Keys / Key West

                                                                            Key West house

                                                                            2 4 28 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 4
                                                                            • 28 nights min
                                                                            • Swimming pool
                                                                            • Air conditioning
                                                                            • Pet Friendly

                                                                            Price per night from

                                                                            $182

                                                                            Price per night from

                                                                            $182

                                                                            (1) Excellent 

                                                                              43

                                                                              Brand New! Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home.

                                                                              Florida Keys / Key West

                                                                              Key West house

                                                                              2 6 30 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 6
                                                                              • 30 nights min
                                                                              • Child Friendly
                                                                              • Car not necessary
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $228

                                                                              Price per night from

                                                                              $228