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Longboat Key Vacation Home Rentals with Outdoor Grill(169)

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Fine Living Relaxation and Enjoyment! Enjoy Pool, Beach and Sunsets
    3 Bedrooms,
  • 2 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 12
$286 - $400
per night

Fine Living Relaxation and Enjoyment! Enjoy Pool, Beach and Sunsets

Book it Now!
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 12
  1. Florida South Central Gulf Coast >
  2. Longboat Key House
#447571vb
    (5)
    Walk to the Beach - Vintage Charm Bungalow on Longboat Key
      3 Bedrooms,
    • 2 Bathrooms
      • , Sleeps 6
    $185 - $225
    per night

    Walk to the Beach - Vintage Charm Bungalow on Longboat Key

    Book it Now!
    3 - 4 night minimum stay
    • 3 BR,
    • 2 BA,
    • Sleeps 6
    1. Florida South Central Gulf Coast >
    2. Longboat Key House
    #414104vb
      (4)
      Hideaway Bay Exclusive Home – Platinum Waterfront Property.
        3 Bedrooms,
      • 3 Bathrooms, 
      • 1 Half Bath
        • , Sleeps 12

      Hideaway Bay Exclusive Home – Platinum Waterfront Property.

      • 3 BR,
      • 3 BA,
      • 1 HF BA,
      • Sleeps 12
      1. Florida South Central Gulf Coast >
      2. Longboat Key House
      #375240vb
        (9)
        Beautiful Family And Pet Friendly Bay View Home
          3 Bedrooms,
        • 2 Bathrooms
          • , Sleeps 8

        Beautiful Family And Pet Friendly Bay View Home

        • 3 BR,
        • 2 BA,
        • Sleeps 8
        1. Florida South Central Gulf Coast >
        2. Longboat Key House
        #450941vb
          Exquisite Beachfront Villa with Private Pool & Stunning Gulf Views!
            5 Bedrooms,
          • 4 Bathrooms, 
          • 1 Half Bath
            • , Sleeps 10

          Exquisite Beachfront Villa with Private Pool & Stunning Gulf Views!

          • 5 BR,
          • 4 BA,
          • 1 HF BA,
          • Sleeps 10
          1. Florida South Central Gulf Coast >
          2. Longboat Key House
          #247100
            (17)
            Special Offer $1000 off Weekly Rental Bookings! (August 25 - December 15)
            Beachfront Property Longboat Key
              2 Bedrooms,
            • 2 Bathrooms
              • , Sleeps 6

            Beachfront Property Longboat Key

            • 2 BR,
            • 2 BA,
            • Sleeps 6
            1. Florida South Central Gulf Coast >
            2. Longboat Key House
            #247170
              1 Review
              Rent the Historic and Famous Longboat Key Beach House Weekly.
                3 Bedrooms,
              • 2 Bathrooms
                • , Sleeps 8

              Rent the Historic and Famous Longboat Key Beach House Weekly.

              • 3 BR,
              • 2 BA,
              • Sleeps 8
              1. Florida South Central Gulf Coast >
              2. Longboat Key House
              #385183vb
                32 Reviews
                Luxurious Villa with Pool, Gourmet Kitchen & Wi-Fi!
                  3 Bedrooms,
                • 3 Bathrooms
                  • , Sleeps 6

                Luxurious Villa with Pool, Gourmet Kitchen & Wi-Fi!

                • 3 BR,
                • 3 BA,
                • Sleeps 6
                1. Florida South Central Gulf Coast >
                2. Longboat Key House
                #344433
                  (5)
                  Special Offer $250 off Weekly Rental Bookings! (April 28 - December 15)
                  Sanctuary of Sun, Water and Relaxation
                    4 Bedrooms,
                  • 3 Bathrooms
                    • , Sleeps 10

                  Sanctuary of Sun, Water and Relaxation

                  • 4 BR,
                  • 3 BA,
                  • Sleeps 10
                  1. Florida South Central Gulf Coast >
                  2. Longboat Key House
                  #442476vb
                    Silver Sands #257
                      1 Bedrooms,
                    • 1 Bathroom
                      • , Sleeps 4
                    $175 - $295
                    per night

                    Silver Sands #257

                    1 - 4 night minimum stay
                    • 1 BR,
                    • 1 BA,
                    • Sleeps 4
                    1. Florida South Central Gulf Coast >
                    2. Longboat Key House
                    #3190787
                      Silver Sands #251
                        1 Bedrooms,
                      • 1 Bathroom
                        • , Sleeps 4
                      $175 - $295
                      per night

                      Silver Sands #251

                      1 - 4 night minimum stay
                      • 1 BR,
                      • 1 BA,
                      • Sleeps 4
                      1. Florida South Central Gulf Coast >
                      2. Longboat Key House
                      #3190775
                        Silver Sands #257A
                          1 Bedrooms,
                        • 1 Bathroom
                          • , Sleeps 2
                        $125 - $170
                        per night

                        Silver Sands #257A

                        1 - 4 night minimum stay
                        • 1 BR,
                        • 1 BA,
                        • Sleeps 2
                        1. Florida South Central Gulf Coast >
                        2. Longboat Key House
                        #3190788
                          Silver Sands #233
                            1 Bedrooms,
                          • 1 Bathroom
                            • , Sleeps 4
                          $135 - $235
                          per night

                          Silver Sands #233

                          1 - 3 night minimum stay
                          • 1 BR,
                          • 1 BA,
                          • Sleeps 4
                          1. Florida South Central Gulf Coast >
                          2. Longboat Key House
                          #3190750
                            Silver Sands #254
                              1 Bedrooms,
                            • 1 Bathroom
                              • , Sleeps 4
                            $175 - $295
                            per night

                            Silver Sands #254

                            1 - 4 night minimum stay
                            • 1 BR,
                            • 1 BA,
                            • Sleeps 4
                            1. Florida South Central Gulf Coast >
                            2. Longboat Key House
                            #3190782
                              Silver Sands #243A
                                1 Bedrooms,
                              • 1 Bathroom
                                • , Sleeps 2
                              $125 - $170
                              per night

                              Silver Sands #243A

                              1 - 4 night minimum stay
                              • 1 BR,
                              • 1 BA,
                              • Sleeps 2
                              1. Florida South Central Gulf Coast >
                              2. Longboat Key House
                              #3190762
                                Charming Canal Home with Private Dock and Enclosed Pool
                                  2 Bedrooms,
                                • 2 Bathrooms
                                  • , Sleeps 8

                                Charming Canal Home with Private Dock and Enclosed Pool

                                • 2 BR,
                                • 2 BA,
                                • Sleeps 8
                                1. Florida South Central Gulf Coast >
                                2. Longboat Key House
                                #928468
                                  (10)
                                  Silver Sands #257S
                                    2 Bedrooms,
                                  • 2 Bathrooms
                                    • , Sleeps 6
                                  $230 - $395
                                  per night

                                  Silver Sands #257S

                                  1 - 4 night minimum stay
                                  • 2 BR,
                                  • 2 BA,
                                  • Sleeps 6
                                  1. Florida South Central Gulf Coast >
                                  2. Longboat Key House
                                  #3190789
                                    Silver Sands #255S
                                      2 Bedrooms,
                                    • 2 Bathrooms
                                      • , Sleeps 6
                                    $230 - $395
                                    per night

                                    Silver Sands #255S

                                    1 - 4 night minimum stay
                                    • 2 BR,
                                    • 2 BA,
                                    • Sleeps 6
                                    1. Florida South Central Gulf Coast >
                                    2. Longboat Key House
                                    #3190785
                                      Silver Sands #256
                                        1 Bedrooms,
                                      • 1 Bathroom
                                        • , Sleeps 4
                                      $175 - $295
                                      per night

                                      Silver Sands #256

                                      1 - 4 night minimum stay
                                      • 1 BR,
                                      • 1 BA,
                                      • Sleeps 4
                                      1. Florida South Central Gulf Coast >
                                      2. Longboat Key House
                                      #3190786
                                        The Beach on Longboat Key #227
                                          1 Bedrooms,
                                        • 1 Bathroom
                                          • , Sleeps 5
                                        $190 - $295
                                        per night

                                        The Beach on Longboat Key #227

                                        1 - 7 night minimum stay
                                        • 1 BR,
                                        • 1 BA,
                                        • Sleeps 5
                                        1. Florida South Central Gulf Coast >
                                        2. Longboat Key House
                                        #3190901
                                          Silver Sands #249
                                            2 Bedrooms,
                                          • 1 Bathroom, 
                                          • 1 Half Bath
                                            • , Sleeps 6
                                          $250 - $425
                                          per night

                                          Silver Sands #249

                                          1 - 4 night minimum stay
                                          • 2 BR,
                                          • 1 BA,
                                          • 1 HF BA,
                                          • Sleeps 6
                                          1. Florida South Central Gulf Coast >
                                          2. Longboat Key House
                                          #3190773
                                            Bay Winds
                                              2 Bedrooms,
                                            • 3 Bathrooms
                                              • , Sleeps 6
                                            $1,900
                                            per week

                                            Bay Winds

                                            7 night minimum stay
                                            • 2 BR,
                                            • 3 BA,
                                            • Sleeps 6
                                            1. Florida South Central Gulf Coast >
                                            2. Longboat Key House
                                            #3240687
                                              Silver Sands #252
                                                1 Bedrooms,
                                              • 1 Bathroom
                                                • , Sleeps 4
                                              $175 - $295
                                              per night

                                              Silver Sands #252

                                              1 - 4 night minimum stay
                                              • 1 BR,
                                              • 1 BA,
                                              • Sleeps 4
                                              1. Florida South Central Gulf Coast >
                                              2. Longboat Key House
                                              #3190778
                                                Silver Sands #253A
                                                  1 Bedrooms,
                                                • 1 Bathroom
                                                  • , Sleeps 2
                                                $125 - $170
                                                per night

                                                Silver Sands #253A

                                                1 - 4 night minimum stay
                                                • 1 BR,
                                                • 1 BA,
                                                • Sleeps 2
                                                1. Florida South Central Gulf Coast >
                                                2. Longboat Key House
                                                #3190780
                                                  Charming Beach House Private Pool, Dock, Beach Access in Longboat Key
                                                    3 Bedrooms,
                                                  • 2 Bathrooms
                                                    • , Sleeps 6
                                                  $1,000 - $1,650
                                                  per week

                                                  Charming Beach House Private Pool, Dock, Beach Access in Longboat Key

                                                  7 night minimum stay
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • Sleeps 6
                                                  1. Florida South Central Gulf Coast >
                                                  2. Longboat Key House
                                                  #3013714
                                                    (8)
                                                    Vacation Paradise Waterfront Home walk to beack pool&boat dock
                                                      3 Bedrooms,
                                                    • 2 Bathrooms
                                                      • , Sleeps 5
                                                    $950
                                                    per week

                                                    Vacation Paradise Waterfront Home walk to beack pool&boat dock

                                                    7 - 28 night minimum stay
                                                    • 3 BR,
                                                    • 2 BA,
                                                    • Sleeps 5
                                                    1. Florida South Central Gulf Coast >
                                                    2. Longboat Key House
                                                    #257978
                                                      (4)
                                                      Tropical Private Island Retreat - a Luxurious Getaway for Memories of a Lifetime
                                                        4 Bedrooms, Sleeps 12
                                                      $8,400
                                                      per week

                                                      Tropical Private Island Retreat - a Luxurious Getaway for Memories of a Lifetime

                                                      7 night minimum stay
                                                      • 4 BR,
                                                      • Sleeps 12
                                                      1. Florida South Central Gulf Coast >
                                                      2. Longboat Key House
                                                      #3006320
                                                        (3)
                                                        Village Home with Yesterday's Charm Walking Distance to Beach and Gulf Bay
                                                          3 Bedrooms,
                                                        • 2 Bathrooms
                                                          • , Sleeps 6
                                                        $1,505
                                                        per week

                                                        Village Home with Yesterday's Charm Walking Distance to Beach and Gulf Bay

                                                        7 night minimum stay
                                                        • 3 BR,
                                                        • 2 BA,
                                                        • Sleeps 6
                                                        1. Florida South Central Gulf Coast >
                                                        2. Longboat Key House
                                                        #384961
                                                          Jessmyth Estate
                                                            4 Bedrooms,
                                                          • 4 Bathrooms, 
                                                          • 1 Half Bath
                                                            • , Sleeps 8
                                                          $11,000 - $13,500
                                                          per month

                                                          Jessmyth Estate

                                                          28 night minimum stay
                                                          • 4 BR,
                                                          • 4 BA,
                                                          • 1 HF BA,
                                                          • Sleeps 8
                                                          1. Florida South Central Gulf Coast >
                                                          2. Longboat Key House
                                                          #3199771
                                                            The Beach on Longboat Key #225
                                                              1 Bedrooms,
                                                            • 1 Bathroom
                                                              • , Sleeps 4
                                                            $170 - $230
                                                            per night

                                                            The Beach on Longboat Key #225

                                                            1 - 7 night minimum stay
                                                            • 1 BR,
                                                            • 1 BA,
                                                            • Sleeps 4
                                                            1. Florida South Central Gulf Coast >
                                                            2. Longboat Key House
                                                            #3190899
                                                              • 1 - 30 of 169
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