Vacation Rentals & House Rentals in Sugarloaf Key

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666 house rentals

(7) Very Good 

    0

    Comfortable condo w/ shared pool, private balcony, and beach access

    Florida Keys / Sugarloaf Key

    Sugarloaf Key house

    2 6 min stay varies

    • 2 bedrooms
    • sleeps 6
    • min stay varies
    • Swimming pool
    • Child Friendly
    • Car not necessary
    “Relaxing and Fun” Very good location..steps away from Smathers beach. Parked car then rode bikes, scooters, and walked around the entire Key. Condo was very nice and comfortable with everything needed for a week or more stay. The only negative is t

    Price per night from

    $281

    Price per night from

    $281

    (3) Very Good 

      25

      Dog-friendly, tropical escape with central location, hot tub, and shared pool

      Florida Keys / Sugarloaf Key

      Sugarloaf Key house

      1 4 min stay varies

      • 1 bedroom
      • sleeps 4
      • min stay varies
      • Swimming pool
      • Child Friendly
      • Car not necessary

      Price per night from

      $179

      Price per night from

      $179

        0

        Large, dog-friendly home on three secluded acres w/ balconies, deck, views

        Florida Keys / Sugarloaf Key

        Sugarloaf Key house

        5 10 28 nights min

        • 5 bedrooms
        • sleeps 10
        • 28 nights min
        • Child Friendly
        • Car not necessary
        • Air conditioning

        Price per night from

        $174

        Price per night from

        $174

        (17) Very Good 

          25

          Cute, updated Key West home w/ private pool - close to Duval Street, dogs ok!

          Florida Keys / Sugarloaf Key

          Sugarloaf Key house

          3 10 min stay varies

          • 3 bedrooms
          • sleeps 10
          • min stay varies
          • Swimming pool
          • Child Friendly
          • Car not necessary
          “What a fun time !!!” I brought my daughter & her boyfriend, my middle daughter and her boyfriend, my son who is a freshman at psu, my girlfriend suzie & myself. We golfed( great golf course ) !!! We jet skiied around key west... you guys have to do

          Price per night from

          $335

          Price per night from

          $335

            0

            Sunrise Suites condo w/balcony, shared pool & hot tub, tennis, & covered parking

            Florida Keys / Sugarloaf Key

            Sugarloaf Key house

            2 6 min stay varies

            • 2 bedrooms
            • sleeps 6
            • min stay varies
            • Swimming pool
            • Child Friendly
            • Car not necessary

            Price per night from

            $171

            Price per night from

            $171

              0

              Newly furnished suite w/ shared pool & hot tub, tennis, balcony, parking, dog ok

              Florida Keys / Sugarloaf Key

              Sugarloaf Key house

              2 6 min stay varies

              • 2 bedrooms
              • sleeps 6
              • min stay varies
              • Swimming pool
              • Child Friendly
              • Car not necessary

              Price per night from

              $162

              Price per night from

              $162

                0

                Shared pool & hot tub, parking spot, balcony - one dog ok! Family friendly!

                Florida Keys / Sugarloaf Key

                Sugarloaf Key house

                2 6 min stay varies

                • 2 bedrooms
                • sleeps 6
                • min stay varies
                • Swimming pool
                • Child Friendly
                • Car not necessary

                Price per night from

                $173

                Price per night from

                $173

                  0

                  Dog-friendly studio condo w/ deck & free WiFi, in the heart of Old Town Key West

                  Florida Keys / Sugarloaf Key

                  Sugarloaf Key studio

                  Studio 2 min stay varies

                  • Studio
                  • sleeps 2
                  • min stay varies
                  • Child Friendly
                  • Car not necessary
                  • Air conditioning

                  Price per night from

                  $118

                  Price per night from

                  $118

                    24

                    Upscale 3BR w/ Chef’s Kitchen, Private Pool & Central Location

                    Florida Keys / Sugarloaf Key

                    Sugarloaf Key house

                    3 6 30 nights min

                    • 3 bedrooms
                    • sleeps 6
                    • 30 nights min
                    • Swimming pool
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $309

                    Price per night from

                    $309

                    (4) Very Good 

                      0

                      Beautiful condo with a deck/patio & shared pool - walk to beaches, Duval & more!

                      Florida Keys / Sugarloaf Key

                      Sugarloaf Key house

                      2 4 7 nights min

                      • 2 bedrooms
                      • sleeps 4
                      • 7 nights min
                      • Swimming pool
                      • Child Friendly
                      • Car not necessary
                      “Key West Vacation Rentals was great to work with.” We loved our stay at Truman annex at the Secret Garden. Working with Key West Vacation Rentals was awesome. Had a little problem when we first checked in with construction going on in the unit next d

                      Price per night from

                      $170

                      Price per night from

                      $170

                        35

                        Spacious home w/ private hot tub, back patio, and awesome location!

                        Florida Keys / Sugarloaf Key

                        Sugarloaf Key house

                        8 24 min stay varies

                        • 8 bedrooms
                        • sleeps 24
                        • min stay varies
                        • Child Friendly
                        • Car not necessary
                        • Air conditioning

                        Price per night from

                        $952

                        Price per night from

                        $952

                        (2) Very Good 

                          0

                          Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok

                          Florida Keys / Sugarloaf Key

                          Sugarloaf Key house

                          1 4 min stay varies

                          • 1 bedroom
                          • sleeps 4
                          • min stay varies
                          • Swimming pool
                          • Child Friendly
                          • Car not necessary

                          Price per night from

                          $193

                          Price per night from

                          $193

                          (1)  

                            0

                            Sunny condo w/ entertainment, balcony, & great location near the beach! Dogs OK!

                            Florida Keys / Sugarloaf Key

                            Sugarloaf Key house

                            1 4 min stay varies

                            • 1 bedroom
                            • sleeps 4
                            • min stay varies
                            • Child Friendly
                            • Car not necessary
                            • Air conditioning

                            Price per night from

                            $178

                            Price per night from

                            $178

                              0

                              Cozy, tropical getaway w/ shared pool - close to shopping and restaurants

                              Florida Keys / Sugarloaf Key

                              Sugarloaf Key studio

                              Studio 2 1 night min

                              • Studio
                              • sleeps 2
                              • 1 night min
                              • Swimming pool
                              • Child Friendly
                              • Car not necessary

                              Price per night from

                              $186

                              Price per night from

                              $186

                                50

                                Dog-friendly condo in prime location - walk to dining & sights, near the beach!

                                Florida Keys / Sugarloaf Key

                                Sugarloaf Key house

                                2 6 28 nights min

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

                                Price per night from

                                $94

                                Price per night from

                                $94

                                (7) Very Good 

                                  52

                                  Dog-friendly home in a quiet neighborhood w/ shared pool & private hot tub!

                                  Florida Keys / Sugarloaf Key

                                  Sugarloaf Key house

                                  2 6 min stay varies

                                  • 2 bedrooms
                                  • sleeps 6
                                  • min stay varies
                                  • Swimming pool
                                  • Child Friendly
                                  • Car not necessary

                                  Price per night from

                                  $243

                                  Price per night from

                                  $243

                                    0

                                    Sprawling condo w/ ocean views, dock, & shared pool - dog-friendly!

                                    Florida Keys / Sugarloaf Key

                                    Sugarloaf Key house

                                    2 6 28 nights min

                                    • 2 bedrooms
                                    • sleeps 6
                                    • 28 nights min
                                    • Swimming pool
                                    • Child Friendly
                                    • Car not necessary

                                    Price per night from

                                    $132

                                    Price per night from

                                    $132

                                      0

                                      Dog-friendly Sunrise Suites condo w/ private balcony, views, shared pool/hot tub

                                      Florida Keys / Sugarloaf Key

                                      Sugarloaf Key house

                                      2 6 min stay varies

                                      • 2 bedrooms
                                      • sleeps 6
                                      • min stay varies
                                      • Swimming pool
                                      • Child Friendly
                                      • Car not necessary

                                      Price per night from

                                      $192

                                      Price per night from

                                      $192

                                      (1) Very Good 

                                        0

                                        Historic house w/ private pool & easy beach access - ideal for groups! Dogs OK!

                                        Florida Keys / Sugarloaf Key

                                        Sugarloaf Key house

                                        7 18 min stay varies

                                        • 7 bedrooms
                                        • sleeps 18
                                        • min stay varies
                                        • Swimming pool
                                        • Child Friendly
                                        • Car not necessary

                                        Price per night from

                                        $1,076

                                        Price per night from

                                        $1,076

                                          0

                                          Spacious suite w/ semi-private porch, a shared pool, & lots of charm!

                                          Florida Keys / Sugarloaf Key

                                          Sugarloaf Key studio

                                          Studio 2 1 night min

                                          • Studio
                                          • sleeps 2
                                          • 1 night min
                                          • Swimming pool
                                          • Child Friendly
                                          • Car not necessary

                                          Price per night from

                                          $146

                                          Price per night from

                                          $146

                                          (1) Excellent 

                                            0

                                            Family friendly condo w/ shared pool, hot tub, & complimentary shuttle! Dogs ok!

                                            Florida Keys / Sugarloaf Key

                                            Sugarloaf Key house

                                            2 6 min stay varies

                                            • 2 bedrooms
                                            • sleeps 6
                                            • min stay varies
                                            • Swimming pool
                                            • Child Friendly
                                            • Car not necessary

                                            Price per night from

                                            $162

                                            Price per night from

                                            $162

                                            (4) Very Good 

                                              0

                                              Contemporary beachside escape with shared pool and close to local attractions

                                              Florida Keys / Sugarloaf Key

                                              Sugarloaf Key house

                                              2 4 7 nights min

                                              • 2 bedrooms
                                              • sleeps 4
                                              • 7 nights min
                                              • Swimming pool
                                              • Child Friendly
                                              • Car not necessary
                                              “261 Lazy Lane- Vacation!!!” The condo was clean and had all of the necessary items needed for a 10 day stay (cleaning products, laundry, etc). It was a nice place to stay and would stay there again next time

                                              Price per night from

                                              $215

                                              Price per night from

                                              $215

                                                48

                                                NEW LISTING! Adorable studio in Historic Seaport -walking distance to waterfront

                                                Florida Keys / Sugarloaf Key

                                                Sugarloaf Key studio

                                                Studio 2 28 nights min

                                                • Studio
                                                • sleeps 2
                                                • 28 nights min
                                                • Car not necessary
                                                • Air conditioning

                                                Price per night from

                                                $115

                                                Price per night from

                                                $115

                                                (14) Very Good 

                                                  0

                                                  Deluxe, ground-floor studio w/ view of the courtyard and pool - close to shops

                                                  Florida Keys / Sugarloaf Key

                                                  Sugarloaf Key studio

                                                  Studio 4 1 night min

                                                  • Studio
                                                  • sleeps 4
                                                  • 1 night min
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Car not necessary
                                                  “Tranquil, beautiful property” The gardens and pool area are just beautiful and tranquil. We enjoyed sitting outside in our quiet, secluded paradise, but were not far from all the hub bub and attractions of Old Key West. We loved our little apartment

                                                  Price per night from

                                                  $196

                                                  Price per night from

                                                  $196

                                                    52

                                                    Dog-friendly home w/ private pool - one block from Duval Street, near Old Town!

                                                    Florida Keys / Sugarloaf Key

                                                    Sugarloaf Key house

                                                    2 4 28 nights min

                                                    • 2 bedrooms
                                                    • sleeps 4
                                                    • 28 nights min
                                                    • Swimming pool
                                                    • Child Friendly
                                                    • Car not necessary

                                                    Price per night from

                                                    $165

                                                    Price per night from

                                                    $165

                                                      36

                                                      Cozy dog-friendly condo w/ shared pool, hot tub, private deck, and parking

                                                      Florida Keys / Sugarloaf Key

                                                      Sugarloaf Key house

                                                      2 6 min stay varies

                                                      • 2 bedrooms
                                                      • sleeps 6
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Child Friendly
                                                      • Car not necessary

                                                      Price per night from

                                                      $176

                                                      Price per night from

                                                      $176

                                                        0

                                                        Dog-friendly retreat w/shared pool & hot tub, tennis, & balcony w/pool views

                                                        Florida Keys / Sugarloaf Key

                                                        Sugarloaf Key house

                                                        2 6 min stay varies

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • min stay varies
                                                        • Swimming pool
                                                        • Child Friendly
                                                        • Car not necessary

                                                        Price per night from

                                                        $176

                                                        Price per night from

                                                        $176

                                                        (16) Very Good 

                                                          0

                                                          Dog-friendly condo w/ private hot tub & shared pool - close to shops & beaches

                                                          Florida Keys / Sugarloaf Key

                                                          Sugarloaf Key house

                                                          2 6 min stay varies

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Car not necessary
                                                          “excellent stay” place exactly as advertised, staff at rental agency are great and helpful with local suggestions

                                                          Price per night from

                                                          $275

                                                          Price per night from

                                                          $275

                                                          (29) Very Good 

                                                            24

                                                            Contemporary seaside cottage w/ private hot tub, shared pool - dogs welcome!

                                                            Florida Keys / Sugarloaf Key

                                                            Sugarloaf Key house

                                                            1 4 min stay varies

                                                            • 1 bedroom
                                                            • sleeps 4
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Child Friendly
                                                            • Car not necessary
                                                            “Private and Perfect” My boyfriend and I were on a road trip which included us camping in the backcountry of the Everglades while we were in Florida, to end our adventure we were looking for a relaxing time in Key West. The prices of hotels during the

                                                            Price per night from

                                                            $186

                                                            Price per night from

                                                            $186

                                                              27

                                                              Sunny dog-friendly condo w/ shared hot tub, pool, & tennis

                                                              Florida Keys / Sugarloaf Key

                                                              Sugarloaf Key house

                                                              2 6 min stay varies

                                                              • 2 bedrooms
                                                              • sleeps 6
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Car not necessary

                                                              Price per night from

                                                              $166

                                                              Price per night from

                                                              $166

                                                                0

                                                                Condo on Duval Street - walk to beach & Southernmost Point, dogs OK

                                                                Florida Keys / Sugarloaf Key

                                                                Sugarloaf Key house

                                                                1 3 min stay varies

                                                                • 1 bedroom
                                                                • sleeps 3
                                                                • min stay varies
                                                                • Child Friendly
                                                                • Car not necessary
                                                                • Air conditioning

                                                                Price per night from

                                                                $149

                                                                Price per night from

                                                                $149

                                                                (2) Excellent 

                                                                  26

                                                                  Dog-friendly home w/ private pool - walk to the beach and restaurants!

                                                                  Florida Keys / Sugarloaf Key

                                                                  Sugarloaf Key house

                                                                  3 8 min stay varies

                                                                  • 3 bedrooms
                                                                  • sleeps 8
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Car not necessary

                                                                  Price per night from

                                                                  $447

                                                                  Price per night from

                                                                  $447

                                                                  (2) Very Good 

                                                                    0

                                                                    Family friendly condo w/tennis, shared pool, hot tub, & private balcony- dogs ok

                                                                    Florida Keys / Sugarloaf Key

                                                                    Sugarloaf Key house

                                                                    2 6 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 6
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Child Friendly
                                                                    • Car not necessary

                                                                    Price per night from

                                                                    $166

                                                                    Price per night from

                                                                    $166

                                                                      0

                                                                      Cozy ground-floor suite in historic home w/ shared pool - close to boardwalk!

                                                                      Florida Keys / Sugarloaf Key

                                                                      Sugarloaf Key studio

                                                                      Studio 2 min stay varies

                                                                      • Studio
                                                                      • sleeps 2
                                                                      • min stay varies
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Car not necessary

                                                                      Price per night from

                                                                      $165

                                                                      Price per night from

                                                                      $165

                                                                        0

                                                                        Cozy room in historic inn - shared pool, great location & air conditioning!

                                                                        Florida Keys / Sugarloaf Key

                                                                        Sugarloaf Key studio

                                                                        Studio 2 1 night min

                                                                        • Studio
                                                                        • sleeps 2
                                                                        • 1 night min
                                                                        • Swimming pool
                                                                        • Child Friendly
                                                                        • Car not necessary

                                                                        Price per night from

                                                                        $155

                                                                        Price per night from

                                                                        $155

                                                                        (1) Average 

                                                                          72

                                                                          Watch sunsets from your deck! Shared pool/hot tub! Perfect for the whole family!

                                                                          Florida Keys / Sugarloaf Key

                                                                          Sugarloaf Key house

                                                                          2 6 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 6
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Car not necessary

                                                                          Price per night from

                                                                          $189

                                                                          Price per night from

                                                                          $189

                                                                          (1) Average 

                                                                            0

                                                                            Welcoming, budget-friendly studio w/ shared heated pool & home comforts

                                                                            Florida Keys / Sugarloaf Key

                                                                            Sugarloaf Key studio

                                                                            Studio 2 1 night min

                                                                            • Studio
                                                                            • sleeps 2
                                                                            • 1 night min
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            • Car not necessary

                                                                            Price per night from

                                                                            $155

                                                                            Price per night from

                                                                            $155

                                                                            (3) Average 

                                                                              0

                                                                              Peaceful, dog-friendly home in a residential neighborhood w/ a shared pool

                                                                              Florida Keys / Sugarloaf Key

                                                                              Sugarloaf Key house

                                                                              2 6 min stay varies

                                                                              • 2 bedrooms
                                                                              • sleeps 6
                                                                              • min stay varies
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              • Car not necessary

                                                                              Price per night from

                                                                              $247

                                                                              Price per night from

                                                                              $247