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2,388 Houses

    18

    3 bedroom/2 bath - Close to Nathan Benderson Park and Seista Key Beach

    Florida / Fruitville

    Fruitville house

    3 6 6 nights min

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

    Price per night from

    $172

    Price per night from

    $172

      8

      Sarasota! 6 miles from world rowing at Benderson, rare opportunity

      Florida / Fruitville

      Fruitville house

      2 6 7 nights min

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

      Price per night from

      $344

      Price per night from

      $344

      (2) Excellent 

        11

        GUEST HOUSE

        Florida / Fruitville

        Fruitville guest house

        1 2 7 nights min

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

        Price per night from

        $80

        Responds fast!
        avg. 3 hours 38 minutes

        Price per night from

        $80

          0

          NEW LISTING! Lakefront condo w/ shared pool, tennis, on-site golf & scenic views

          Florida / Fruitville

          Fruitville house

          2 4 28 nights min

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

          Price per night from

          $81

          Responds fast!
          avg. 2 hours 30 minutes

          Price per night from

          $81

            14

            3br./3ba. Beautiful Home in Paradise.

            Florida / Fruitville

            Fruitville house

            3 7 2 nights min

            • 3 bedrooms
            • sleeps 7
            • 2 nights min
            • Nearest beach 15 mi
            • Child Friendly
            • Air conditioning

            Price per night from

            $138

            Price per night from

            $138

              41

              Florida Dream house

              Florida / Fruitville

              Fruitville house

              3 8 3 nights min

              • 3 bedrooms
              • sleeps 8
              • 3 nights min
              • Nearest beach 10 mi
              • Child Friendly
              • Air conditioning

              Price per night from

              $126

              Price per night from

              $126

                36

                Cozy 1 bedm/1 bathm apartment renovated overlooking the Groves Golf Course

                Florida / Fruitville

                Fruitville townhouse

                1 3 7 nights min

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

                Price per night from

                $98

                Price per night from

                $98

                  28

                  NEW! Spacious Sarasota House w/Screened Lanai+Pool

                  Florida / Fruitville

                  Fruitville house

                  4 10 min stay varies

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

                  Price per night from

                  $184

                  Responds fast!
                  avg. 7 minutes

                  Price per night from

                  $184

                    21

                    AAA Accommodation in The Meadows - Sarasota

                    Florida / Fruitville

                    Fruitville condo

                    2 6 14 nights min

                    • 2 bedrooms
                    • sleeps 6
                    • 14 nights min
                    • Nearest beach 14 mi
                    • Swimming pool
                    • Child Friendly

                    Price per night from

                    $99

                    Responds fast!
                    avg. 1 hour 3 minutes

                    Price per night from

                    $99

                    Great rentals within 20 miles that match your search

                    Distance approx 6.46 km from Fruitville

                      26

                      Bright 2 bedroom home 10 minutes to Siesta Key - Lots of restaurants nearby

                      Florida / Gulf Gate Branch

                      Gulf Gate Branch house

                      2 4 min stay varies

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

                      Price per night from

                      $96

                      Responds fast!
                      avg. 3 hours 25 minutes

                      Price per night from

                      $96

                      Distance approx 7.82 km from Fruitville

                      (6) Very Good 

                        17

                        Starfish Unit at Sunset Beach Resort Beach Front Property

                        Southwest Gulf Coast / Sarasota

                        Sarasota apartment

                        1 4 min stay varies

                        • 1 bedroom
                        • sleeps 4
                        • min stay varies
                        • Beach / lakeside relaxation
                        • Child Friendly
                        • Car not necessary

                        Price per night from

                        $285

                        Responds fast!
                        avg. 3 hours 16 minutes

                        Price per night from

                        $285

                        Distance approx 8.33 km from Fruitville

                          24

                          Monthly Rental, 2 bed, 2 bath, Ocean view.

                          Southwest Gulf Coast / Sarasota

                          Sarasota condo

                          2 6 30 nights min

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

                          Price per night from

                          $114

                          Price per night from

                          $114

                          Distance approx 6.07 km from Fruitville

                            8

                            5 Minutes to Siesta Key Beach

                            Florida / Siesta Key

                            Siesta Key house

                            2 4 30 nights min

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

                            Price per night from

                            $244

                            Price per night from

                            $244

                            Distance approx 15.64 km from Fruitville

                              22

                              Palma Sola Bay Hideaway ~Private Pool and Spa near Anna Maria Island and Beaches

                              Florida / Palma Sola

                              Palma Sola house

                              3 10 3 nights min

                              • 3 bedrooms
                              • sleeps 10
                              • 3 nights min
                              • Beach / lakeside relaxation
                              • Swimming pool
                              • Child Friendly

                              Price per night from

                              $223

                              Responds fast!
                              avg. 1 hour 41 minutes

                              Price per night from

                              $223

                              Distance approx 6.84 km from Fruitville

                                22

                                Timberwoods Vacation Villas Best Value in Sarasota - Villa 3

                                Southwest Gulf Coast / Sarasota

                                Sarasota villa

                                2 6 7 nights min

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

                                Price per night from

                                $273

                                Responds fast!
                                avg. 2 hours 37 minutes

                                Price per night from

                                $273

                                Distance approx 13.55 km from Fruitville

                                  19

                                  Beautiful Water View Bright, Airy, Spacious, 2BR 2 BA Venetian Golf and River Cl

                                  Southwest Gulf Coast / Venice

                                  Venice house

                                  2 4 min stay varies

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

                                  Price per night from

                                  $92

                                  Responds fast!
                                  avg. 3 hours 0 minutes

                                  Price per night from

                                  $92

                                  Distance approx 7.09 km from Fruitville

                                    7

                                    Siesta Key Vacation Townhouse directly across the street from #1 Beach in the US

                                    Florida / Siesta Key

                                    Siesta Key townhouse

                                    2 6 7 nights min

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

                                    Price per night from

                                    $226

                                    Price per night from

                                    $226

                                    Distance approx 7.44 km from Fruitville

                                    (1) Excellent 

                                      35

                                      Gulf Beach, Pool And Walk To Siesta Key Village

                                      Southwest Gulf Coast / Sarasota

                                      Sarasota apartment

                                      2 6 min stay varies

                                      • 2 bedrooms
                                      • sleeps 6
                                      • min stay varies
                                      • Nearest beach 0.1 mi
                                      • Swimming pool
                                      • Child Friendly
                                      “wonderful” perfect location, just steps to the village yet quiet area. the most beautiful private beach. we were there during spring break was so nice to have our own beach just for owners and guest.

                                      Price per night from

                                      $130

                                      Price per night from

                                      $130

                                      Distance approx 17.37 km from Fruitville

                                        30

                                        Special April Rates! Rooftop Views, 1/2 Block to the Beach and Bridge Street!

                                        Anna Maria Island / Bradenton Beach

                                        Bradenton Beach house

                                        3 8 min stay varies

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

                                        Price per night from

                                        $387

                                        Price per night from

                                        $387

                                        Distance approx 15.28 km from Fruitville

                                          24

                                          Pvt Pool Home Mins to Anna Maria Is & IMG Academy

                                          Southwest Gulf Coast / Bradenton

                                          Bradenton house

                                          3 6 7 nights min

                                          • 3 bedrooms
                                          • sleeps 6
                                          • 7 nights min
                                          • Child Friendly
                                          • Pet Friendly

                                          Price per night from

                                          $327

                                          Price per night from

                                          $327

                                          Distance approx 7.3 km from Fruitville

                                            8

                                            5 minute walk to Siesta Key Beach and Village!

                                            Florida / Siesta Key

                                            Siesta Key house

                                            1 4 2 nights min

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

                                            Price per night from

                                            $170

                                            Price per night from

                                            $170

                                            Distance approx 6.91 km from Fruitville

                                              16

                                              Act Fast! Cancellation opens EASTER 2019! Book now for 2019 future holidays!

                                              Florida / Siesta Key

                                              Siesta Key condo

                                              2 5 14 nights min

                                              • 2 bedrooms
                                              • sleeps 5
                                              • 14 nights min
                                              • Swimming pool
                                              • Child Friendly
                                              • Air conditioning

                                              Price per night from

                                              $166

                                              Price per night from

                                              $166

                                              Distance approx 3.25 km from Fruitville Show on Map

                                                16

                                                Villa with golf course view with solar heated pool

                                                Florida / Lakewood Ranch

                                                Lakewood Ranch villa

                                                3 6 min stay varies

                                                • 3 bedrooms
                                                • sleeps 6
                                                • min stay varies
                                                • Nearest beach 19 mi
                                                • Swimming pool
                                                • Ask about children

                                                Price per night from

                                                $152

                                                Price per night from

                                                $152

                                                Distance approx 3.82 km from Fruitville Show on Map

                                                  15

                                                  By "Dr Beach" 15 Minute Drive from Mature Gated Community

                                                  Southwest Gulf Coast / Sarasota

                                                  Sarasota house

                                                  2 6 3 nights min

                                                  • 2 bedrooms
                                                  • sleeps 6
                                                  • 3 nights min
                                                  • Child Friendly
                                                  • Air conditioning

                                                  Price per night from

                                                  $103

                                                  Responds fast!
                                                  avg. 2 hours 26 minutes

                                                  Price per night from

                                                  $103

                                                  Distance approx 12.7 km from Fruitville

                                                  (1) Excellent 

                                                    21

                                                    Penthouse Condo At Riverstrand Golf & Country Club

                                                    Southwest Gulf Coast / Bradenton

                                                    Bradenton apartment

                                                    2 6 30 nights min

                                                    • 2 bedrooms
                                                    • sleeps 6
                                                    • 30 nights min
                                                    • Nearest beach 12 mi
                                                    • Swimming pool
                                                    • Car not necessary

                                                    Price per night from

                                                    $77

                                                    Price per night from

                                                    $77

                                                    Distance approx 19.31 km from Fruitville

                                                      13

                                                      Beach Townhouses #54522

                                                      Anna Maria Island / Holmes Beach

                                                      Holmes Beach townhouse

                                                      2 6 27 nights min

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

                                                      Price per night from

                                                      $185

                                                      Price per night from

                                                      $185

                                                      Distance approx 5.61 km from Fruitville

                                                        9

                                                        Braden River Bayou Cottage

                                                        Florida / Lakewood Ranch

                                                        Lakewood Ranch cottage

                                                        1 2 5 nights min

                                                        • 1 bedroom
                                                        • sleeps 2
                                                        • 5 nights min
                                                        • Nearest beach 10 mi
                                                        • Air conditioning
                                                        • Private garden

                                                        Price per night from

                                                        $126

                                                        Responds fast!
                                                        avg. 3 hours 15 minutes

                                                        Price per night from

                                                        $126

                                                        Distance approx 17.03 km from Fruitville

                                                        (25) Excellent 

                                                          46

                                                          Sublime Interlude

                                                          Anna Maria Island / Bradenton Beach

                                                          Bradenton Beach apartment

                                                          2 5 min stay varies

                                                          • 2 bedrooms
                                                          • sleeps 5
                                                          • min stay varies
                                                          • Beach / lakeside relaxation
                                                          • Nearest beach 0 mi
                                                          • Child Friendly
                                                          “Wonderful place” We have spent the month of January here for the past seven years. We love the area and thoroughly enjoy the beach and weather. The owners are very helpful and accommodating. I highly recommend them.

                                                          Price per night from

                                                          $262

                                                          Price per night from

                                                          $262

                                                          Distance approx 7.5 km from Fruitville

                                                          (21) Excellent 

                                                          Certificate of Excellence

                                                            42

                                                            8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (3)

                                                            Florida / Siesta Key

                                                            Siesta Key house

                                                            1 4 3 nights min

                                                            • 1 bedroom
                                                            • sleeps 4
                                                            • 3 nights min
                                                            • Beach / lakeside relaxation
                                                            • Nearest beach 0.1 mi
                                                            • Child Friendly
                                                            “Old man and the sea unit c” The owner of the unit was extremely helpful from start to finish. Prior to arrival receiving a large information e mail containing everything you would ever need to know about the unit and area was a great benefit. The unit

                                                            Certificate of Excellence

                                                            Price per night from

                                                            $127

                                                            Responds fast!
                                                            avg. 2 hours 13 minutes

                                                            Price per night from

                                                            $127

                                                            Distance approx 15.13 km from Fruitville

                                                              10

                                                              2 Bed, 2Bath, 6Sleeps.

                                                              Southwest Gulf Coast / Venice

                                                              Venice house

                                                              2 6 30 nights min

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

                                                              Price per night from

                                                              $82

                                                              Responds fast!
                                                              avg. 48 minutes

                                                              Price per night from

                                                              $82

                                                              Distance approx 6.77 km from Fruitville

                                                                54

                                                                Conveniently Located Secluded Villa

                                                                Florida / Gulf Gate Branch

                                                                Gulf Gate Branch villa

                                                                2 6 7 nights min

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

                                                                Price per night from

                                                                $114

                                                                Price per night from

                                                                $114

                                                                Distance approx 7.31 km from Fruitville

                                                                (2) Very Good 

                                                                  10

                                                                  2 bedroom/1 bath Contemporary Beach Cottage

                                                                  Florida / Siesta Key

                                                                  Siesta Key house

                                                                  2 6 4 nights min

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

                                                                  Price per night from

                                                                  $194

                                                                  Price per night from

                                                                  $194

                                                                  Distance approx 5.78 km from Fruitville

                                                                  (10) Very Good 

                                                                    42

                                                                    Tropical Pool Home Near Siesta Key, Pet Friendly! Private POOL

                                                                    Southwest Gulf Coast / Sarasota

                                                                    Sarasota house

                                                                    2 4 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 4
                                                                    • min stay varies
                                                                    • Nearest beach 3 mi
                                                                    • Swimming pool
                                                                    • Ask about children

                                                                    Price per night from

                                                                    $80

                                                                    Price per night from

                                                                    $80

                                                                    Distance approx 5.37 km from Fruitville Show on Map

                                                                      22

                                                                      5-Star Serenata Luxury Condo Close to Beach

                                                                      Southwest Gulf Coast / Sarasota

                                                                      Sarasota condo

                                                                      2 6 30 nights min

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

                                                                      Price per night from

                                                                      $84

                                                                      Responds fast!
                                                                      avg. 43 minutes

                                                                      Price per night from

                                                                      $84

                                                                      Distance approx 13.15 km from Fruitville

                                                                      (1) Excellent 

                                                                        19

                                                                        Private Home for Slps 4+1,15min “Blue Wave”Beaches

                                                                        Southwest Gulf Coast / Bradenton

                                                                        Bradenton house

                                                                        2 5 3 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 5
                                                                        • 3 nights min
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $137

                                                                        Price per night from

                                                                        $137

                                                                        Distance approx 7.01 km from Fruitville

                                                                          14

                                                                          CANCELLATION OPENS MARCH 28th ON! HURRY BEFORE IT'S GONE

                                                                          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

                                                                          $166

                                                                          Price per night from

                                                                          $166

                                                                          Distance approx 19.74 km from Fruitville

                                                                            51

                                                                            Runaway (ANN630)

                                                                            Anna Maria Island / Holmes Beach

                                                                            Holmes Beach apartment

                                                                            2 6 7 nights min

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

                                                                            Price per night from

                                                                            $207

                                                                            Responds fast!
                                                                            avg. 2 hours 55 minutes

                                                                            Price per night from

                                                                            $207

                                                                            Distance approx 18.94 km from Fruitville

                                                                              12

                                                                              On The Beach Home 3103

                                                                              Anna Maria Island / Holmes Beach

                                                                              Holmes Beach house

                                                                              5 10 7 nights min

                                                                              • 5 bedrooms
                                                                              • sleeps 10
                                                                              • 7 nights min
                                                                              • Swimming pool
                                                                              • Car not necessary

                                                                              Price per night from

                                                                              $585

                                                                              Price per night from

                                                                              $585