Vacation Rentals & Apartments in Big Pine Key

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263 apartments

    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

    $198

    Responds fast!
    avg. 3 hours 4 minutes

    Price per night from

    $198

    (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

      $113

      Responds fast!
      avg. 2 hours 20 minutes

      Price per night from

      $113

        13

        3 bedroom canal front home minutes from open Water!

        Florida Keys / Big Pine Key

        Big Pine Key house

        3 10 30 nights min

        • 3 bedrooms
        • sleeps 10
        • 30 nights min
        • Child Friendly
        • Air conditioning
        • Private garden

        Price per night from

        $172

        Responds fast!
        avg. 3 hours 41 minutes

        Price per night from

        $172

          10

          Big Pine 2/2 ,Water Views

          Florida Keys / Big Pine Key

          Big Pine Key house

          2 4 30 nights min

          • 2 bedrooms
          • sleeps 4
          • 30 nights min
          • Child Friendly
          • Air conditioning

          Price per night from

          $131

          Responds fast!
          avg. 3 hours 36 minutes

          Price per night from

          $131

            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

            $172

            Price per night from

            $172

              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

              $163

              Responds fast!
              avg. 3 hours 2 minutes

              Price per night from

              $163

              (3) Average 

                19

                Waterfront Home in The Fabulous Florida Keys!

                Florida Keys / Big Pine Key

                Big Pine Key house

                2 6 28 nights min

                • 2 bedrooms
                • sleeps 6
                • 28 nights min
                • Beach / lakeside relaxation
                • Nearest beach 10 mi
                • Child Friendly

                Price per night from

                $287

                Price per night from

                $287

                  24

                  Experience the Keys like a Local at this Spacious Canal Front Home with Dock!

                  Florida Keys / Big Pine Key

                  Big Pine Key house

                  3 7 28 nights min

                  • 3 bedrooms
                  • sleeps 7
                  • 28 nights min
                  • Child Friendly
                  • Air conditioning

                  Price per night from

                  $126

                  Responds fast!
                  avg. 55 minutes

                  Price per night from

                  $126

                    12

                    Hideaway Bay

                    Florida Keys / Big Pine Key

                    Big Pine Key house

                    2 4 31 nights min

                    • 2 bedrooms
                    • sleeps 4
                    • 31 nights min
                    • Child Friendly
                    • Air conditioning
                    • Pet Friendly

                    Price per night from

                    $108

                    Price per night from

                    $108

                      10

                      Blue Heron

                      Florida Keys / Big Pine Key

                      Big Pine Key house

                      2 4 30 nights min

                      • 2 bedrooms
                      • sleeps 4
                      • 30 nights min
                      • Ask about children
                      • Air conditioning
                      • Pet Friendly

                      Price per night from

                      $93

                      Price per night from

                      $93

                        27

                        Island Time (both halves of duplex)

                        Florida Keys / Big Pine Key

                        Big Pine Key house

                        5 10 30 nights min

                        • 5 bedrooms
                        • sleeps 10
                        • 30 nights min
                        • Ask about children
                        • Air conditioning
                        • Pet Friendly

                        Price per night from

                        $197

                        Price per night from

                        $197

                        (1)  

                          16

                          Our Island Thing

                          Florida Keys / Big Pine Key

                          Big Pine Key house

                          4 8 30 nights min

                          • 4 bedrooms
                          • sleeps 8
                          • 30 nights min
                          • Ask about children
                          • Air conditioning
                          • Ask about pets

                          Price per night from

                          $200

                          Price per night from

                          $200

                            16

                            Unwind at a waterfront home, a short drive to fun, shops, dining & 30min to Key

                            Florida Keys / Big Pine Key

                            Big Pine Key house

                            2 6 28 nights min

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

                            Price per night from

                            $137

                            Responds fast!
                            avg. 55 minutes

                            Price per night from

                            $137

                              28

                              Florida Keys Fisherman and Divers Paradise

                              Florida Keys / Big Pine Key

                              Big Pine Key house

                              4 12 30 nights min

                              • 4 bedrooms
                              • sleeps 12
                              • 30 nights min
                              • Swimming pool
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $286

                              Price per night from

                              $286

                              (1) Excellent 

                                14

                                Breeze Swept

                                Florida Keys / Big Pine Key

                                Big Pine Key house

                                3 6 30 nights min

                                • 3 bedrooms
                                • sleeps 6
                                • 30 nights min
                                • Ask about children
                                • Air conditioning
                                • Pet Friendly

                                Price per night from

                                $197

                                Price per night from

                                $197

                                  15

                                  Island Time 1 (half of duplex)

                                  Florida Keys / Big Pine Key

                                  Big Pine Key house

                                  2 4 30 nights min

                                  • 2 bedrooms
                                  • sleeps 4
                                  • 30 nights min
                                  • Ask about children
                                  • Air conditioning
                                  • Pet Friendly

                                  Price per night from

                                  $93

                                  Price per night from

                                  $93

                                  (10) Excellent 

                                    17

                                    Reel Paradise - Big Pine Key

                                    Florida Keys / Big Pine Key

                                    Big Pine Key house

                                    3 6 30 nights min

                                    • 3 bedrooms
                                    • sleeps 6
                                    • 30 nights min
                                    • Beach / lakeside relaxation
                                    • Child Friendly
                                    • Car not necessary

                                    Price per night from

                                    $160

                                    Price per night from

                                    $160

                                      16

                                      Island Time 2 (half of duplex)

                                      Florida Keys / Big Pine Key

                                      Big Pine Key house

                                      3 6 30 nights min

                                      • 3 bedrooms
                                      • sleeps 6
                                      • 30 nights min
                                      • Ask about children
                                      • Air conditioning
                                      • Pet Friendly

                                      Price per night from

                                      $100

                                      Price per night from

                                      $100

                                        12

                                        Lost In Paradise

                                        Florida Keys / Big Pine Key

                                        Big Pine Key house

                                        2 4 30 nights min

                                        • 2 bedrooms
                                        • sleeps 4
                                        • 30 nights min
                                        • Ask about children
                                        • Air conditioning
                                        • Pet Friendly

                                        Price per night from

                                        $140

                                        Price per night from

                                        $140

                                          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

                                          $99

                                          Responds fast!
                                          avg. 2 hours 40 minutes

                                          Price per night from

                                          $99

                                          Great rentals within 20 miles that match your search

                                          Distance approx 19.7 km from Big Pine Key

                                          (13) Excellent 

                                            26

                                            2 Great Waterfront FL Keys Homes - 1 Low Price

                                            Florida Keys / Marathon

                                            Marathon house

                                            4 12 7 nights min

                                            • 4 bedrooms
                                            • sleeps 12
                                            • 7 nights min
                                            • Beach / lakeside relaxation
                                            • Nearest beach 2 mi
                                            • Child Friendly
                                            “Excellent Stay!” We rented out both sides for the week and we couldn't have asked for a better location! Great fishing, lobstering, and diving. We took the boat out almost everyday right from the house. Just enough room for our 9 people plus 1 baby. I

                                            Price per night from

                                            $370

                                            Price per night from

                                            $370

                                            Distance approx 18.82 km from Big Pine Key

                                            (20) Excellent 

                                              45

                                              OUTSTANDING Oceanfront House with Pool and Deep water dockage!!

                                              Florida Keys / Marathon

                                              Marathon house

                                              4 10 7 nights min

                                              • 4 bedrooms
                                              • sleeps 10
                                              • 7 nights min
                                              • Beach / lakeside relaxation
                                              • Nearest beach 3 mi
                                              • Swimming pool
                                              “Marathon house” A great house with an awesome ocean view! The house was very clean and the kitchen was well stocked with all we needed. We especially looked the pool area and boat dock. It accommodated our 38 ft fishing boat we brought with no problem

                                              Price per night from

                                              $651

                                              Responds fast!
                                              avg. 2 hours 53 minutes

                                              Price per night from

                                              $651

                                              Distance approx 6.25 km from Big Pine Key Show on Map

                                                12

                                                Caribbean House

                                                Lower Keys / Summerland Key

                                                Summerland Key house

                                                2 4 30 nights min

                                                • 2 bedrooms
                                                • sleeps 4
                                                • 30 nights min
                                                • Ask about children
                                                • Air conditioning
                                                • Ask about pets

                                                Price per night from

                                                $87

                                                Price per night from

                                                $87

                                                Distance approx 7.61 km from Big Pine Key Show on Map

                                                  12

                                                  Cudjoe Ocean Shores

                                                  Florida Keys / Cudjoe Key

                                                  Cudjoe Key house

                                                  3 6 30 nights min

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

                                                  Price per night from

                                                  $97

                                                  Price per night from

                                                  $97

                                                  Distance approx 18.39 km from Big Pine Key

                                                  (4) Very Good 

                                                    9

                                                    Reef Resort Getaway 205

                                                    Florida Keys / Marathon

                                                    Marathon studio

                                                    Studio 3 7 nights min

                                                    • Studio
                                                    • sleeps 3
                                                    • 7 nights min
                                                    • Swimming pool
                                                    • Child Friendly
                                                    • Air conditioning

                                                    Price per night from

                                                    $195

                                                    Responds fast!
                                                    avg. 3 hours 56 minutes

                                                    Price per night from

                                                    $195

                                                    Distance approx 7.76 km from Big Pine Key Show on Map

                                                      12

                                                      Paradise Bay

                                                      Florida Keys / Cudjoe Key

                                                      Cudjoe Key house

                                                      3 6 30 nights min

                                                      • 3 bedrooms
                                                      • sleeps 6
                                                      • 30 nights min
                                                      • Ask about children
                                                      • Air conditioning
                                                      • Pet Friendly

                                                      Price per night from

                                                      $107

                                                      Price per night from

                                                      $107

                                                      Distance approx 17.46 km from Big Pine Key

                                                        16

                                                        Let's Go Fishing! Old Florida Living - trendy 2 bedroom-2 bath Villa in Goodland

                                                        Florida Keys / Marathon

                                                        Marathon condo

                                                        2 4 7 nights min

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • 7 nights min
                                                        • Swimming pool
                                                        • Ask about children
                                                        • Air conditioning

                                                        Price per night from

                                                        $129

                                                        Price per night from

                                                        $129

                                                        Distance approx 15.74 km from Big Pine Key

                                                          4

                                                          Outstanding 5-star rating resort

                                                          Marathon / Marathon Shores

                                                          Marathon Shores villa

                                                          1 4 2 nights min

                                                          • 1 bedroom
                                                          • sleeps 4
                                                          • 2 nights min
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $285

                                                          Price per night from

                                                          $285

                                                          Distance approx 16.96 km from Big Pine Key

                                                            47

                                                            New Rental Sombero Beach

                                                            Marathon / Marathon Shores

                                                            Marathon Shores house

                                                            4 10 7 nights min

                                                            • 4 bedrooms
                                                            • sleeps 10
                                                            • 7 nights min
                                                            • Swimming pool
                                                            • Child Friendly
                                                            • Air conditioning

                                                            Price per night from

                                                            $854

                                                            Price per night from

                                                            $854

                                                            Distance approx 5.74 km from Big Pine Key Show on Map

                                                              19

                                                              Gone Fishing

                                                              Lower Keys / Summerland Key

                                                              Summerland Key house

                                                              3 6 28 nights min

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

                                                              Price per night from

                                                              $210

                                                              Price per night from

                                                              $210

                                                              Distance approx 3.49 km from Big Pine Key Show on Map

                                                                19

                                                                Bahia Azul

                                                                Florida Keys / Ramrod Key

                                                                Ramrod Key house

                                                                4 8 30 nights min

                                                                • 4 bedrooms
                                                                • sleeps 8
                                                                • 30 nights min
                                                                • Ask about children
                                                                • Air conditioning
                                                                • Ask about pets

                                                                Price per night from

                                                                $229

                                                                Price per night from

                                                                $229

                                                                Distance approx 4.73 km from Big Pine Key Show on Map

                                                                  19

                                                                  Sunset Bay (weekly rental)

                                                                  Florida Keys / Ramrod Key

                                                                  Ramrod Key house

                                                                  2 4 7 nights min

                                                                  • 2 bedrooms
                                                                  • sleeps 4
                                                                  • 7 nights min
                                                                  • Ask about children
                                                                  • Air conditioning
                                                                  • Pet Friendly

                                                                  Price per night from

                                                                  $270

                                                                  Price per night from

                                                                  $270

                                                                  Distance approx 8.03 km from Big Pine Key Show on Map

                                                                    11

                                                                    Mermaid's Rest

                                                                    Florida Keys / Cudjoe Key

                                                                    Cudjoe Key house

                                                                    3 6 30 nights min

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

                                                                    Price per night from

                                                                    $133

                                                                    Price per night from

                                                                    $133

                                                                    Distance approx 7.68 km from Big Pine Key Show on Map

                                                                      28

                                                                      Tropical Canal Home

                                                                      Florida Keys / Cudjoe Key

                                                                      Cudjoe Key house

                                                                      3 6 30 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 6
                                                                      • 30 nights min
                                                                      • Child Friendly
                                                                      • Air conditioning
                                                                      • Ask about pets

                                                                      Price per night from

                                                                      $191

                                                                      Price per night from

                                                                      $191

                                                                      Distance approx 12.27 km from Big Pine Key

                                                                      (4) Excellent 

                                                                        11

                                                                        Key West's only Real Beach House

                                                                        Florida Keys / Key West

                                                                        Key West guest house

                                                                        2 4 7 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 4
                                                                        • 7 nights min
                                                                        • Beach / lakeside relaxation
                                                                        • Swimming pool
                                                                        • Ask about children

                                                                        Price per night from

                                                                        $392

                                                                        Price per night from

                                                                        $392

                                                                        Distance approx 2.12 km from Big Pine Key Show on Map

                                                                          17

                                                                          Buccaneer Boathouse

                                                                          Lower Keys / Little Torch Key

                                                                          Little Torch Key house

                                                                          2 6 30 nights min

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

                                                                          Price per night from

                                                                          $113

                                                                          Price per night from

                                                                          $113

                                                                          Distance approx 19.08 km from Big Pine Key

                                                                          (2) Excellent 

                                                                            26

                                                                            FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 8 w/ 60 Feet of Dockage

                                                                            Marathon / Marathon Shores

                                                                            Marathon Shores house

                                                                            2 8 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 8
                                                                            • min stay varies
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $257

                                                                            Responds fast!
                                                                            avg. 1 hour 39 minutes

                                                                            Price per night from

                                                                            $257

                                                                            Distance approx 13.19 km from Big Pine Key

                                                                              12

                                                                              Green Turtle Landing

                                                                              Florida Keys / Sugarloaf

                                                                              Sugarloaf house

                                                                              3 6 30 nights min

                                                                              • 3 bedrooms
                                                                              • sleeps 6
                                                                              • 30 nights min
                                                                              • Ask about children
                                                                              • Air conditioning
                                                                              • Pet Friendly

                                                                              Price per night from

                                                                              $140

                                                                              Price per night from

                                                                              $140

                                                                              About Big Pine Key

                                                                              Big Pine Key, Florida

                                                                              This may seem like a small island, but it has a big heart. You'll always be welcome in Big Pine Key—and there's always something to do. 

                                                                              Explore this unique part of Monroe County on your next trip and book your vacation rental with FlipKey—that way you'll have the best place to stay!

                                                                              About Big Pine Key, Florida

                                                                              Tourists come to Big Pine Key for a bit of sunshine and small town living. You'll quickly become part of the community during your stay, so much so that you may not want to leave!

                                                                              Embrace the low-key lifestyle and escape from your busy life for a week or two. Feel like a local—grab groceries from Winn-Dixie and explore the shopping center. 

                                                                              There are plenty of restaurants, a Beal's Outlet store and a RadioShack—we bet you didn't think it’d have all of that, did you?

                                                                              The shopping center is also home to the visitors’ center for the National Key Deer Refuge. It's worth going there to find out more about the area, and the local wildlife.

                                                                              While it may seem like a sleepy town, it's got pretty wild nightlife—there are restaurants, clubs and bars that stay open until late and have great deals on drinks.

                                                                              What to do

                                                                              Visit the Blue Hole—it's an abandoned rock quarry from years ago. It's now filled with fresh water and is a great place to spot the local wildlife, including birds, snakes, alligators and green iguanas.

                                                                              Seeing those animals makes for a great day out, but the species Big Pine Key is most famous for is Key deer. Head to the refuge, where you'll see the majority of them. They're an endangered species, but they're well looked after here. Don't be shocked at how small they are—they're the size of a large dog, and very cute.

                                                                              If you've had your fill of nature, try one of the many water sports on offer. You can go boating, fishing, scuba diving snorkeling and more during your stay. Just take your pick!

                                                                              Looking for a great beach? There are stretches of white sand at Bahia Honda State Park. It's a great place to spend a day.

                                                                              Top travel tips

                                                                              As deer are everywhere—including the road—you should pay special attention when driving. They tend to come out at night, so keep your wits about you.

                                                                              Where there's great fishing, there's great seafood restaurants, and Big Pine Key doesn't disappoint. Try some of the local produce during your stay.

                                                                              Make sure you check out the flea market, too. It's open on Sundays and has everything you could possibly need during your vacation.

                                                                              Whether you're here for the beach, hospitality or wildlife, you'll have a great time in Big Pine Key. Explore and discover everything this island has to offer during your stay by booking your rental accommodation on FlipKey.