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291 vacation rentals

(2) Very Good 

    24

    Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

    Florida / Siesta Key

    Siesta Key apartment

    1 4 min stay varies

    • 1 bedroom
    • sleeps 4
    • min stay varies
    • Swimming pool
    • Child Friendly
    • Air conditioning

    Price per night from

    $123

    Price per night from

    $123

      38

      NEW Private Siesta Key Vacation Rental Home W/ Heated Pool on Quiet Street

      Florida / Siesta Key

      Siesta Key condo

      3 6 min stay varies

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

      Price per night from

      $261

      Price per night from

      $261

      (6) Very Good 

        28

        Just Minutes from the White Sandy Siesta Beach

        Florida / Siesta Key

        Siesta Key condo

        1 4 1 night min

        • 1 bedroom
        • sleeps 4
        • 1 night min
        • Nearest beach 4 mi
        • Swimming pool
        • Child Friendly
        “Just Right” Our condo was perfect for us! There was everything we needed inside and stuff for the beach! There was a Publix right across the street and many places to eat. The drive to Siesta Key was right up the road which was a plus as well! When we
        …see more

        Price per night from

        $91

        Price per night from

        $91

        (2) Very Good 

          38

          Grand accomdation on USA #1 Beach - Siesta Key Fl

          Florida / Siesta Key

          Siesta Key apartment

          2 5 14 nights min

          • 2 bedrooms
          • sleeps 5
          • 14 nights min
          • Beach / lakeside relaxation
          • Nearest beach 1 mi
          • Swimming pool

          Price per night from

          $99

          Price per night from

          $99

          (4) Excellent 

            49

            Siesta Key 2 BR, 2 1/2 Bath - *Across From Beach - Pool-view* - Newly Renovated

            Florida / Siesta Key

            Siesta Key apartment

            2 7 min stay varies

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

            Price per night from

            $164

            Responds fast!
            avg. 1 hour 45 minutes

            Price per night from

            $164

            (1) Excellent 

              28

              1 Block to the Beach on Siesta Key Vacation Rental Home with Swimming Pool

              Florida / Siesta Key

              Siesta Key house

              3 6 min stay varies

              • 3 bedrooms
              • sleeps 6
              • min stay varies
              • Child Friendly
              • Air conditioning
              • Pet Friendly
              “Great place, super location” We thoroughly enjoyed our stay at your home. It was very spacious, clean and inviting. We had everything we needed and the location is wonderful. Thanks and we would definitly recommend your home to others
              …see more

              Price per night from

              $344

              Price per night from

              $344

                33

                Walk to the Beach / Ride to the Village / Pool Home in Siesta Key - Free WiFi

                Florida / Siesta Key

                Siesta Key condo

                3 6 min stay varies

                • 3 bedrooms
                • sleeps 6
                • min stay varies
                • Child Friendly
                • Air conditioning
                • Pet Friendly

                Price per night from

                $263

                Price per night from

                $263

                  28

                  Luxury Siesta Key Vacation Rental W/ Pool, Spa, and Walking Distance to Beach

                  Florida / Siesta Key

                  Siesta Key condo

                  3 8 min stay varies

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

                  Price per night from

                  $488

                  Price per night from

                  $488

                    24

                    Siesta Key Village Townhome with Heated Pool and Walking Distance to Beaches

                    Florida / Siesta Key

                    Siesta Key condo

                    2 6 min stay varies

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

                    Price per night from

                    $281

                    Price per night from

                    $281

                      35

                      Immaculate Siesta Key Beachside Private Vacation Home w/ Large Heated Pool

                      Florida / Siesta Key

                      Siesta Key condo

                      3 8 min stay varies

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

                      Price per night from

                      $393

                      Price per night from

                      $393

                        14

                        Siesta Key Public Beach

                        Florida / Siesta Key

                        Siesta Key condo

                        2 6 7 nights min

                        • 2 bedrooms
                        • sleeps 6
                        • 7 nights min
                        • Nearest beach 0.1 mi
                        • Swimming pool
                        • Child Friendly

                        Price per night from

                        $161

                        Price per night from

                        $161

                          29

                          Waterfront Siesta Key Vacation Rental Condo with Heated Pool and Water Views

                          Florida / Siesta Key

                          Siesta Key condo

                          2 4 min stay varies

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

                          Price per night from

                          $123

                          Price per night from

                          $123

                            24

                            Walk to the Village or the Beach, Everything is in Reach from this SK Rental

                            Florida / Siesta Key

                            Siesta Key condo

                            2 6 min stay varies

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

                            Price per night from

                            $219

                            Price per night from

                            $219

                              7

                              Sunset Royale - 302

                              Florida / Siesta Key

                              Siesta Key apartment

                              1 4 min stay varies

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

                              Price per night from

                              $145

                              Price per night from

                              $145

                                25

                                Luxury Siesta Key Vacation Rental Home with Heated Pool and Beach Access

                                Florida / Siesta Key

                                Siesta Key condo

                                4 10 min stay varies

                                • 4 bedrooms
                                • sleeps 10
                                • min stay varies
                                • Swimming pool
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $343

                                Price per night from

                                $343

                                  17

                                  Fantastic Island House of Siesta w/pool Walk to the beach

                                  Florida / Siesta Key

                                  Siesta Key apartment

                                  2 6 2 nights min

                                  • 2 bedrooms
                                  • sleeps 6
                                  • 2 nights min
                                  • Beach / lakeside relaxation
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $217

                                  Price per night from

                                  $217

                                    36

                                    A Piece of Paradise just a short Walk to Siesta Key Beach with Heated Pool

                                    Florida / Siesta Key

                                    Siesta Key condo

                                    1 6 min stay varies

                                    • 1 bedroom
                                    • sleeps 6
                                    • min stay varies
                                    • Swimming pool
                                    • Child Friendly
                                    • Air conditioning

                                    Price per night from

                                    $294

                                    Price per night from

                                    $294

                                      25

                                      Coastal Siesta Key Vacation Rental Home W/ Heated Pool and Beach Access

                                      Florida / Siesta Key

                                      Siesta Key condo

                                      3 6 min stay varies

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

                                      Price per night from

                                      $264

                                      Price per night from

                                      $264

                                        25

                                        Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

                                        Florida / Siesta Key

                                        Siesta Key condo

                                        2 6 min stay varies

                                        • 2 bedrooms
                                        • sleeps 6
                                        • min stay varies
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $123

                                        Price per night from

                                        $123

                                          25

                                          Siesta Key Beach Townhouse with Heated Pool and Accommodates up to 8 Guests

                                          Florida / Siesta Key

                                          Siesta Key condo

                                          2 8 min stay varies

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

                                          Price per night from

                                          $133

                                          Price per night from

                                          $133

                                            10

                                            Sunset Royale 214

                                            Florida / Siesta Key

                                            Siesta Key apartment

                                            2 4 min stay varies

                                            • 2 bedrooms
                                            • sleeps 4
                                            • min stay varies
                                            • Child Friendly
                                            • Car not necessary
                                            • Air conditioning

                                            Price per night from

                                            $165

                                            Price per night from

                                            $165

                                              24

                                              Spacious vacation rental condo with lagoon views, beach access, and pool

                                              Florida / Siesta Key

                                              Siesta Key condo

                                              3 6 min stay varies

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

                                              Price per night from

                                              $158

                                              Price per night from

                                              $158

                                                25

                                                Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

                                                Florida / Siesta Key

                                                Siesta Key condo

                                                1 4 min stay varies

                                                • 1 bedroom
                                                • sleeps 4
                                                • min stay varies
                                                • Child Friendly
                                                • Air conditioning

                                                Price per night from

                                                $109

                                                Price per night from

                                                $109

                                                  26

                                                  Fully renovated ground floor poolside unit at Bay Oaks with fishing pier-D31

                                                  Florida / Siesta Key

                                                  Siesta Key apartment

                                                  2 6 7 nights min

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

                                                  Price per night from

                                                  $182

                                                  Price per night from

                                                  $182

                                                    9

                                                    Sunset Royale - 204

                                                    Florida / Siesta Key

                                                    Siesta Key apartment

                                                    1 4 min stay varies

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

                                                    Price per night from

                                                    $145

                                                    Price per night from

                                                    $145

                                                      24

                                                      Excellent Sarasota Vacation Rental Just Minutes to Siesta Key and Downtown

                                                      Florida / Siesta Key

                                                      Siesta Key condo

                                                      2 8 min stay varies

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

                                                      Price per night from

                                                      $178

                                                      Price per night from

                                                      $178

                                                        9

                                                        Sunset Royale -106

                                                        Florida / Siesta Key

                                                        Siesta Key condo

                                                        2 6 min stay varies

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • min stay varies
                                                        • Child Friendly
                                                        • Car not necessary
                                                        • Air conditioning

                                                        Price per night from

                                                        $165

                                                        Price per night from

                                                        $165

                                                          24

                                                          4 Bedroom Key West Style Home W/ Heated Pool, Close to Village and Beaches

                                                          Florida / Siesta Key

                                                          Siesta Key condo

                                                          4 8 min stay varies

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

                                                          Price per night from

                                                          $207

                                                          Price per night from

                                                          $207

                                                            15

                                                            Sunset Royale - 308

                                                            Florida / Siesta Key

                                                            Siesta Key condo

                                                            1 2 min stay varies

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

                                                            Price per night from

                                                            $145

                                                            Price per night from

                                                            $145

                                                              8

                                                              Sunset Royale 208

                                                              Florida / Siesta Key

                                                              Siesta Key apartment

                                                              1 4 min stay varies

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

                                                              Price per night from

                                                              $145

                                                              Price per night from

                                                              $145

                                                                31

                                                                Spacious Siesta Key Canal Front Vacation Rental House with Large Heated Pool

                                                                Florida / Siesta Key

                                                                Siesta Key condo

                                                                3 10 14 nights min

                                                                • 3 bedrooms
                                                                • sleeps 10
                                                                • 14 nights min
                                                                • Swimming pool
                                                                • Child Friendly
                                                                • Air conditioning

                                                                Price per night from

                                                                $263

                                                                Price per night from

                                                                $263

                                                                  26

                                                                  Affordable Ground Floor Siesta Key Vacation Rental with Heated Pool Access

                                                                  Florida / Siesta Key

                                                                  Siesta Key condo

                                                                  2 6 min stay varies

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

                                                                  Price per night from

                                                                  $116

                                                                  Price per night from

                                                                  $116

                                                                    12

                                                                    Beachside Bliss !

                                                                    Florida / Siesta Key

                                                                    Siesta Key apartment

                                                                    1 3 1 night min

                                                                    • 1 bedroom
                                                                    • sleeps 3
                                                                    • 1 night min
                                                                    • Beach / lakeside relaxation
                                                                    • Swimming pool
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $148

                                                                    Price per night from

                                                                    $148

                                                                      13

                                                                      Sunset Royale 104

                                                                      Florida / Siesta Key

                                                                      Siesta Key apartment

                                                                      1 2 min stay varies

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

                                                                      Price per night from

                                                                      $158

                                                                      Price per night from

                                                                      $158

                                                                        23

                                                                        Zen Den

                                                                        Florida / Siesta Key

                                                                        Siesta Key apartment

                                                                        1 4 2 nights min

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

                                                                        Price per night from

                                                                        $171

                                                                        Price per night from

                                                                        $171

                                                                          24

                                                                          Renovated Spacious Three Suite Siesta Key Vacation Rental Home W/ Heated Pool

                                                                          Florida / Siesta Key

                                                                          Siesta Key condo

                                                                          3 7 min stay varies

                                                                          • 3 bedrooms
                                                                          • sleeps 7
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $248

                                                                          Price per night from

                                                                          $248

                                                                            11

                                                                            Sunset Royale - 114

                                                                            Florida / Siesta Key

                                                                            Siesta Key apartment

                                                                            2 4 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 4
                                                                            • min stay varies
                                                                            • Child Friendly
                                                                            • Car not necessary
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $163

                                                                            Price per night from

                                                                            $163

                                                                              17

                                                                              Sunset Royale - 112

                                                                              Florida / Siesta Key

                                                                              Siesta Key condo

                                                                              2 4 min stay varies

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • min stay varies
                                                                              • Child Friendly
                                                                              • Car not necessary
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $165

                                                                              Price per night from

                                                                              $165