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612 Houses

    31

    Canal-Front Paradise! Spacious 3BR w/ Private Pool, Boat Dock & Deck

    Florida Keys / Sugarloaf

    Sugarloaf house

    3 6 30 nights min

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

    Price per night from

    $319

    Price per night from

    $319

      11

      Tranquility in Paradise - Sugarloaf Key (17 miles to Key West)

      Florida Keys / Sugarloaf

      Sugarloaf house

      5 9 28 nights min

      • 5 bedrooms
      • sleeps 9
      • 28 nights min
      • Child Friendly
      • Pet Friendly

      Price per night from

      $332

      Price per night from

      $332

      Great rentals within 20 miles that match your search

      Distance approx 16.77 km from Sugarloaf

      (36) Excellent 

      Certificate of Excellence

        17

        1/2 Block to Duval, World of its own -Nassau Suite

        Florida Keys / Key West

        Key West apartment

        2 6 min stay varies

        • 2 bedrooms
        • sleeps 6
        • min stay varies
        • Swimming pool
        • Car not necessary
        • Air conditioning
        “Our wedding family stayed here awesome” Fabulous. Clean roomy pool fantastic. Short walk to schooners Wharf Both inside and outside area were excellent
        …see more

        Certificate of Excellence

        Price per night from

        $329

        Price per night from

        $329

        Distance approx 16.87 km from Sugarloaf

        (3) Very Good 

          16

          Conch Haven Old Town 1/1 MONTHLY Rental

          Florida Keys / Key West

          Key West apartment

          1 4 30 nights min

          • 1 bedroom
          • sleeps 4
          • 30 nights min
          • Beach / lakeside relaxation
          • Child Friendly
          • Car not necessary

          Price per night from

          $96

          Responds fast!
          avg. 3 hours 4 minutes

          Price per night from

          $96

          Distance approx 12.28 km from Sugarloaf

          (19) Excellent 

            26

            Spectacular Atlantic Ocean View Condo (MONTHLY)

            Florida Keys / Key West

            Key West apartment

            2 6 28 nights min

            • 2 bedrooms
            • sleeps 6
            • 28 nights min
            • Beach / lakeside relaxation
            • Swimming pool
            • Child Friendly
            “Amazing Views And A Great Condo” My wife and I stayed here on our honeymoon and were absolutely 100% pleased with the condo. I have to honestly say it was the nicest condo either of us have stayed in. The view was amazing and the patio was very tranqu
            …see more

            Price per night from

            $339

            Price per night from

            $339

            Distance approx 17 km from Sugarloaf

            (63) Excellent 

              26

              Casa Del Sol, a Key West Vacation (Truman Annex)

              Florida Keys / Key West

              Key West house

              2 6 7 nights min

              • 2 bedrooms
              • sleeps 6
              • 7 nights min
              • Beach / lakeside relaxation
              • Swimming pool
              • Child Friendly
              “awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.
              …see more

              Price per night from

              $236

              Responds fast!
              avg. 1 hour 8 minutes

              Price per night from

              $236

              Distance approx 16.85 km from Sugarloaf

              (3) Average 

                24

                Casa Havana

                Florida Keys / Key West

                Key West house

                3 8 min stay varies

                • 3 bedrooms
                • sleeps 8
                • min stay varies
                • Child Friendly
                • Air conditioning
                • Private garden

                Price per night from

                $800

                Price per night from

                $800

                Distance approx 12.88 km from Sugarloaf

                  24

                  Sunrise Drive

                  Florida Keys / Big Pine Key

                  Big Pine Key house

                  3 8 min stay varies

                  • 3 bedrooms
                  • sleeps 8
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Nearest beach 8 mi
                  • Suitable for children age 5+

                  Price per night from

                  $204

                  Responds fast!
                  avg. 3 hours 4 minutes

                  Price per night from

                  $204

                  Distance approx 10.46 km from Sugarloaf

                    16

                    Charming Elevated Waterfront Home

                    Florida Keys / Big Pine Key

                    Big Pine Key house

                    1 4 30 nights min

                    • 1 bedroom
                    • sleeps 4
                    • 30 nights min
                    • Child Friendly
                    • Air conditioning
                    • Ask about pets

                    Price per night from

                    $167

                    Responds fast!
                    avg. 3 hours 2 minutes

                    Price per night from

                    $167

                    Distance approx 11.43 km from Sugarloaf

                    (1) Excellent 

                      20

                      Fisherman's Paradise in the Heart of Big Pine Key

                      Florida Keys / Big Pine Key

                      Big Pine Key house

                      3 6 30 nights min

                      • 3 bedrooms
                      • sleeps 6
                      • 30 nights min
                      • Child Friendly

                      Price per night from

                      $117

                      Responds fast!
                      avg. 2 hours 20 minutes

                      Price per night from

                      $117

                      Distance approx 16.38 km from Sugarloaf

                        6

                        Coconut Beach

                        Florida Keys / Key West

                        Key West apartment

                        1 4 7 nights min

                        • 1 bedroom
                        • sleeps 4
                        • 7 nights min
                        • Beach / lakeside relaxation
                        • Swimming pool
                        • Child Friendly

                        Price per night from

                        $270

                        Responds fast!
                        avg. 3 hours 11 minutes

                        Price per night from

                        $270

                        Distance approx 11.44 km from Sugarloaf

                          16

                          New Listing! Beautiful Canal front , Key Deer and jacuzzi.

                          Florida Keys / Big Pine Key

                          Big Pine Key house

                          3 8 28 nights min

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

                          Price per night from

                          $177

                          Price per night from

                          $177

                          Distance approx 4.06 km from Sugarloaf Show on Map

                          (2) Excellent 

                            34

                            Oksana's Tropical Beach Oasis

                            Florida Keys / Cudjoe Key

                            Cudjoe Key house

                            4 14 7 nights min

                            • 4 bedrooms
                            • sleeps 14
                            • 7 nights min
                            • Nearest beach 10 mi
                            • Swimming pool
                            • Child Friendly

                            Price per night from

                            $617

                            Price per night from

                            $617

                            Distance approx 16.24 km from Sugarloaf

                            (1) Very Good 

                              18

                              "Little Paradise" Historic Seaport Old Town Key West

                              Florida Keys / Key West

                              Key West house

                              2 4 7 nights min

                              • 2 bedrooms
                              • sleeps 4
                              • 7 nights min
                              • Child Friendly
                              • Air conditioning
                              • Private garden

                              Price per night from

                              $505

                              Responds fast!
                              avg. 2 hours 56 minutes

                              Price per night from

                              $505

                              Distance approx 15.02 km from Sugarloaf

                                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

                                $336

                                Responds fast!
                                avg. 3 hours 57 minutes

                                Price per night from

                                $336

                                Distance approx 16.77 km from Sugarloaf

                                (3) Very Good 

                                  31

                                  Key West Wabi Sabi ~ Weekly Rental

                                  Florida Keys / Key West

                                  Key West house

                                  4 8 min stay varies

                                  • 4 bedrooms
                                  • sleeps 8
                                  • min stay varies
                                  • Swimming pool
                                  • Ask about children
                                  • Air conditioning

                                  Price per night from

                                  $797

                                  Price per night from

                                  $797

                                  Distance approx 16.68 km from Sugarloaf

                                  (1) Excellent 

                                    19

                                    Villa Nouveau Key West ~ Weekly Rental

                                    Florida Keys / Key West

                                    Key West house

                                    4 8 min stay varies

                                    • 4 bedrooms
                                    • sleeps 8
                                    • min stay varies
                                    • Swimming pool
                                    • Ask about children
                                    • Air conditioning

                                    Price per night from

                                    $899

                                    Price per night from

                                    $899

                                    Distance approx 16.48 km from Sugarloaf

                                    (9) Very Good 

                                      30

                                      Classic Key West Estate ~ Weekly Rental

                                      Florida Keys / Key West

                                      Key West house

                                      7 14 min stay varies

                                      • 7 bedrooms
                                      • sleeps 14
                                      • min stay varies
                                      • Swimming pool
                                      • Ask about children
                                      • Air conditioning

                                      Price per night from

                                      $1,542

                                      Price per night from

                                      $1,542

                                      Distance approx 16.83 km from Sugarloaf

                                        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

                                        $505

                                        Price per night from

                                        $505

                                        Distance approx 16.61 km from Sugarloaf

                                        (12) Very Good 

                                          20

                                          Key West Dreamin' ~ Weekly Rental

                                          Florida Keys / Key West

                                          Key West house

                                          2 6 min stay varies

                                          • 2 bedrooms
                                          • sleeps 6
                                          • min stay varies
                                          • Swimming pool
                                          • Ask about children
                                          • Air conditioning

                                          Price per night from

                                          $565

                                          Price per night from

                                          $565

                                          Distance approx 12.14 km from Sugarloaf

                                            26

                                            Key West Harbour Oceanfront Suites #2

                                            Florida Keys / Key West

                                            Key West apartment

                                            2 5 min stay varies

                                            • 2 bedrooms
                                            • sleeps 5
                                            • min stay varies
                                            • Swimming pool
                                            • Child Friendly
                                            • Air conditioning

                                            Price per night from

                                            $308

                                            Price per night from

                                            $308

                                            Distance approx 12.13 km from Sugarloaf

                                            (1) Excellent 

                                              25

                                              Key West Harbour Oceanfront Suites #3

                                              Florida Keys / Key West

                                              Key West apartment

                                              2 5 min stay varies

                                              • 2 bedrooms
                                              • sleeps 5
                                              • min stay varies
                                              • Swimming pool
                                              • Child Friendly
                                              • Air conditioning

                                              Price per night from

                                              $308

                                              Price per night from

                                              $308

                                              Distance approx 17 km from Sugarloaf

                                              (11) Excellent 

                                                42

                                                3 BIKES, Truman Annex w/2 PATIOS, A POOL, WIFI, & PARKING

                                                Florida Keys / Key West

                                                Key West condo

                                                2 4 7 nights min

                                                • 2 bedrooms
                                                • sleeps 4
                                                • 7 nights min
                                                • Nearest beach 0.2 mi
                                                • Swimming pool
                                                • Child Friendly

                                                Price per night from

                                                $202

                                                Responds fast!
                                                avg. 57 minutes

                                                Price per night from

                                                $202

                                                Distance approx 17.09 km from Sugarloaf

                                                (2) Excellent 

                                                  21

                                                  Truman Treasure

                                                  Florida Keys / Key West

                                                  Key West apartment

                                                  3 5 7 nights min

                                                  • 3 bedrooms
                                                  • sleeps 5
                                                  • 7 nights min
                                                  • Nearest beach 0.49 mi
                                                  • Swimming pool
                                                  • Child Friendly

                                                  Price per night from

                                                  $573

                                                  Price per night from

                                                  $573

                                                  Distance approx 16.68 km from Sugarloaf

                                                  (2) Average 

                                                    55

                                                    The Meeting Point - Key West ~ Weekly Rental

                                                    Florida Keys / Key West

                                                    Key West house

                                                    11 24 min stay varies

                                                    • 11 bedrooms
                                                    • sleeps 24
                                                    • min stay varies
                                                    • Swimming pool
                                                    • Child Friendly
                                                    • Car not necessary

                                                    Price per night from

                                                    $2,518

                                                    Price per night from

                                                    $2,518

                                                    Distance approx 16.92 km from Sugarloaf

                                                      7

                                                      Just Off Duval 3 Bedroom Private Home with Pool

                                                      Florida Keys / Key West

                                                      Key West house

                                                      3 6 30 nights min

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

                                                      Price per night from

                                                      $392

                                                      Responds fast!
                                                      avg. 46 minutes

                                                      Price per night from

                                                      $392

                                                      Distance approx 15.42 km from Sugarloaf

                                                      (8) Very Good 

                                                        14

                                                        3 Bedroom Oceanfront Condo Key West

                                                        Florida Keys / Key West

                                                        Key West apartment

                                                        3 6 30 nights min

                                                        • 3 bedrooms
                                                        • sleeps 6
                                                        • 30 nights min
                                                        • Beach / lakeside relaxation
                                                        • Swimming pool
                                                        • Child Friendly

                                                        Price per night from

                                                        $471

                                                        Responds fast!
                                                        avg. 46 minutes

                                                        Price per night from

                                                        $471

                                                        Distance approx 16.39 km from Sugarloaf

                                                          15

                                                          Cabana Boheme ~ Monthly Rental

                                                          Florida Keys / Key West

                                                          Key West house

                                                          3 6 30 nights min

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • 30 nights min
                                                          • Swimming pool
                                                          • Ask about children
                                                          • Air conditioning

                                                          Price per night from

                                                          $136

                                                          Price per night from

                                                          $136

                                                          Distance approx 9.13 km from Sugarloaf

                                                            17

                                                            Two Story Stilt Home with a Wraparound Deck in a Tropical Paradise in Fl Keys

                                                            Florida Keys / Ramrod Key

                                                            Ramrod Key house

                                                            2 6 30 nights min

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

                                                            Price per night from

                                                            $138

                                                            Price per night from

                                                            $138

                                                            Distance approx 11.87 km from Sugarloaf

                                                              35

                                                              Caribbean Cove

                                                              Florida Keys / Big Pine Key

                                                              Big Pine Key house

                                                              2 9 28 nights min

                                                              • 2 bedrooms
                                                              • sleeps 9
                                                              • 28 nights min
                                                              • Child Friendly
                                                              • Air conditioning
                                                              • Private garden

                                                              Price per night from

                                                              $102

                                                              Responds fast!
                                                              avg. 3 hours 17 minutes

                                                              Price per night from

                                                              $102

                                                              Distance approx 16.4 km from Sugarloaf

                                                                25

                                                                Old Town *Pink Conch House" with Pool

                                                                Florida Keys / Key West

                                                                Key West house

                                                                4 8 30 nights min

                                                                • 4 bedrooms
                                                                • sleeps 8
                                                                • 30 nights min
                                                                • Child Friendly

                                                                Price per night from

                                                                $294

                                                                Price per night from

                                                                $294

                                                                Distance approx 16.54 km from Sugarloaf

                                                                  13

                                                                  Hidden Story-Book Cottage ~ Monthly Rental

                                                                  Florida Keys / Key West

                                                                  Key West cottage

                                                                  1 2 30 nights min

                                                                  • 1 bedroom
                                                                  • sleeps 2
                                                                  • 30 nights min
                                                                  • Ask about children
                                                                  • Air conditioning
                                                                  • Private garden

                                                                  Price per night from

                                                                  $113

                                                                  Price per night from

                                                                  $113

                                                                  Distance approx 16.47 km from Sugarloaf

                                                                    17

                                                                    key west tree house

                                                                    Florida Keys / Key West

                                                                    Key West apartment

                                                                    1 3 30 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 3
                                                                    • 30 nights min
                                                                    • Nearest beach 1 mi
                                                                    • Child Friendly
                                                                    • Car not necessary

                                                                    Price per night from

                                                                    $197

                                                                    Price per night from

                                                                    $197

                                                                    Distance approx 16.93 km from Sugarloaf

                                                                    (3) Very Good 

                                                                      24

                                                                      HISTORIC KEY WEST - Turtle House - Sleeps 6

                                                                      Florida Keys / Key West

                                                                      Key West house

                                                                      2 6 min stay varies

                                                                      • 2 bedrooms
                                                                      • sleeps 6
                                                                      • min stay varies
                                                                      • Nearest beach 0.8 mi
                                                                      • Swimming pool
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $587

                                                                      Price per night from

                                                                      $587

                                                                      Distance approx 15.47 km from Sugarloaf

                                                                        24

                                                                        By The Beautiful Sea ~ A Key West Beach Front Condo ~ Weekly Rental

                                                                        Florida Keys / Key West

                                                                        Key West house

                                                                        3 6 min stay varies

                                                                        • 3 bedrooms
                                                                        • sleeps 6
                                                                        • min stay varies
                                                                        • Beach / lakeside relaxation
                                                                        • Swimming pool
                                                                        • Ask about children

                                                                        Price per night from

                                                                        $494

                                                                        Price per night from

                                                                        $494

                                                                        Distance approx 16.82 km from Sugarloaf

                                                                          13

                                                                          The Green House - Garden

                                                                          Florida Keys / Key West

                                                                          Key West apartment

                                                                          1 4 3 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 4
                                                                          • 3 nights min
                                                                          • Child Friendly

                                                                          Price per night from

                                                                          $313

                                                                          Price per night from

                                                                          $313

                                                                          Distance approx 16.73 km from Sugarloaf

                                                                          (20) Excellent 

                                                                            22

                                                                            Harbor Walk Hideaways

                                                                            Florida Keys / Key West

                                                                            Key West b and b

                                                                            4 8 min stay varies

                                                                            • 4 bedrooms
                                                                            • sleeps 8
                                                                            • min stay varies
                                                                            • Beach / lakeside relaxation
                                                                            • Nearest beach 0.2 mi
                                                                            • Swimming pool
                                                                            “Location, Location, Location” We were a group of 8 and rented the entire compound! The place was in an amazing location that was easily accessible to everything. We had everything we needed onsite and if we had any questions, Phyllis was always just
                                                                            …see more

                                                                            Price per night from

                                                                            $925

                                                                            Price per night from

                                                                            $925

                                                                            Distance approx 17.05 km from Sugarloaf

                                                                            (17) Excellent 

                                                                              10

                                                                              Best Old Town Location in Key West

                                                                              Florida Keys / Key West

                                                                              Key West townhouse

                                                                              2 6 7 nights min

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

                                                                              Price per night from

                                                                              $264

                                                                              Price per night from

                                                                              $264