Vacation Rentals with Pool in Sarasota

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Filtering by: Swimming pool

1,957 vacation rentals

(1) Excellent 

    37

    Oceanfront home w/sunset views of Sarasota Bay

    Southwest Gulf Coast / Sarasota

    Sarasota house

    3 8 min stay varies

    • 3 bedrooms
    • sleeps 8
    • min stay varies
    • Nearest beach 10 mi
    • Swimming pool
    • Child Friendly

    Price per night from

    $400

    Responds fast!
    avg. 1 hour 19 minutes

    Price per night from

    $400

    (4) Excellent 

      13

      Siesta Beach Cottage

      Southwest Gulf Coast / Sarasota

      Sarasota apartment

      2 6 2 nights min

      • 2 bedrooms
      • sleeps 6
      • 2 nights min
      • Swimming pool
      • Child Friendly
      • Air conditioning
      “Beautiful place!” Enjoyed our stay in Sarasota on this property! We were not there much but when we were it felt like home. Very clean inside and out. The owner Kimberly showed us were everything was when we got there. Had a nice pool but too cold out
      …see more

      Price per night from

      $216

      Price per night from

      $216

      (1) Excellent 

        16

        Newly Updated 3 Bedroom Pool Home - Close to Beach

        Southwest Gulf Coast / Sarasota

        Sarasota house

        3 7 min stay varies

        • 3 bedrooms
        • sleeps 7
        • min stay varies
        • Beach / lakeside relaxation
        • Nearest beach 13 mi
        • Swimming pool

        Price per night from

        $143

        Responds fast!
        avg. 37 minutes

        Price per night from

        $143

          30

          Huge 4BR/4BA w/ Screened Pool, BBQ, Ping-Pong, & Sunroom - Walk to Lido Beach

          Southwest Gulf Coast / Sarasota

          Sarasota house

          4 8 3 nights min

          • 4 bedrooms
          • sleeps 8
          • 3 nights min
          • Swimming pool
          • Child Friendly
          • Air conditioning

          Price per night from

          $318

          Price per night from

          $318

          (1) Excellent 

            35

            Fido Friendly w/Fenced Yard, Spa/Swimming Pool, Wifi, Large Ranch Home, Large L

            Southwest Gulf Coast / Sarasota

            Sarasota house

            3 7 min stay varies

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

            Price per night from

            $121

            Responds fast!
            avg. 4 minutes

            Price per night from

            $121

            (25) Excellent 

              44

              Canal Pool Home (15 mins to Siesta Key Beach)

              Southwest Gulf Coast / Sarasota

              Sarasota house

              4 8 6 nights min

              • 4 bedrooms
              • sleeps 8
              • 6 nights min
              • Beach / lakeside relaxation
              • Nearest beach 10 mi
              • Swimming pool
              “Canal pool home” The home was wonderful. Plenty of space for everyone. Kids loved the pool & adults too. Fabulous time on Siesta Key, Longboat Key & Venice beaches.
              …see more

              Price per night from

              $219

              Responds fast!
              avg. 1 hour 40 minutes

              Price per night from

              $219

                27

                3BR/3BA w/ Fenced Pool, Hot Tub, Patio & Outdoor Kitchen - 1 Block to Bay

                Southwest Gulf Coast / Sarasota

                Sarasota house

                3 6 3 nights min

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

                Price per night from

                $232

                Price per night from

                $232

                  13

                  FLORIDA POOL HOME FOR RENT

                  Southwest Gulf Coast / Sarasota

                  Sarasota house

                  3 6 7 nights min

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

                  Price per night from

                  $148

                  Price per night from

                  $148

                  (4) Excellent 

                    28

                    Pet Friendly Pool Home Close to Beaches & Town

                    Southwest Gulf Coast / Sarasota

                    Sarasota house

                    3 7 min stay varies

                    • 3 bedrooms
                    • sleeps 7
                    • min stay varies
                    • Beach / lakeside relaxation
                    • Swimming pool
                    • Child Friendly

                    Price per night from

                    $172

                    Responds fast!
                    avg. 3 hours 29 minutes

                    Price per night from

                    $172

                    (2) Very Good 

                      29

                      Family friendly house with pool/spa

                      Sarasota / Lido Key

                      Lido Key house

                      3 7 min stay varies

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

                      Price per night from

                      $201

                      Responds fast!
                      avg. 3 hours 56 minutes

                      Price per night from

                      $201

                        26

                        House 3 miles to Siesta Key - Walk to Gulf Gate!

                        Southwest Gulf Coast / Sarasota

                        Sarasota house

                        2 6 min stay varies

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

                        Price per night from

                        $163

                        Responds fast!
                        avg. 47 minutes

                        Price per night from

                        $163

                        (12) Excellent 

                          58

                          Luxury Condominium at Siesta Dunes Beachside Pool Hot Tub Tennis Sun Deck

                          Southwest Gulf Coast / Sarasota

                          Sarasota apartment

                          2 6 7 nights min

                          • 2 bedrooms
                          • sleeps 6
                          • 7 nights min
                          • Beach / lakeside relaxation
                          • Swimming pool
                          • Child Friendly
                          “Very comfortable lodgings” Loads of extras in this unit. Well cared for, updated very nicely. Disappointed that the large deck was taken out of service, possibly for a year! It seems to me that usage could have been sustained by posting signs that cau
                          …see more

                          Price per night from

                          $256

                          Price per night from

                          $256

                            0

                            Family-friendly home near attractions w/private pool - snowbirds welcome!

                            Southwest Gulf Coast / Sarasota

                            Sarasota house

                            3 8 29 nights min

                            • 3 bedrooms
                            • sleeps 8
                            • 29 nights min
                            • Swimming pool
                            • Child Friendly
                            • Car not necessary

                            Price per night from

                            $77

                            Responds fast!
                            avg. 1 hour 58 minutes

                            Price per night from

                            $77

                            (1) Very Good 

                              17

                              Spectacular Vacation Experience

                              Southwest Gulf Coast / Sarasota

                              Sarasota house

                              3 7 29 nights min

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

                              Price per night from

                              $207

                              Responds fast!
                              avg. 2 hours 15 minutes

                              Price per night from

                              $207

                              (4) Excellent 

                                25

                                Southgate: Lovely remodeled 3 bedroom pool villa 2.5 Miles from Siesta Key

                                Southwest Gulf Coast / Sarasota

                                Sarasota villa

                                3 6 min stay varies

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

                                Price per night from

                                $182

                                Price per night from

                                $182

                                (1) Excellent 

                                  21

                                  Renovated ! Heated pool! House Close To USA's Best Beach! Great Rates!

                                  Southwest Gulf Coast / Sarasota

                                  Sarasota villa

                                  4 8 7 nights min

                                  • 4 bedrooms
                                  • sleeps 8
                                  • 7 nights min
                                  • Nearest beach 2 mi
                                  • Swimming pool
                                  • Child Friendly

                                  Price per night from

                                  $264

                                  Responds fast!
                                  avg. 3 hours 28 minutes

                                  Price per night from

                                  $264

                                    28

                                    4BR Casa Azul w/ Private Pool, Fire Pit, Covered Pergola - Near Bay, Downtown

                                    Southwest Gulf Coast / Sarasota

                                    Sarasota house

                                    4 12 min stay varies

                                    • 4 bedrooms
                                    • sleeps 12
                                    • min stay varies
                                    • Swimming pool
                                    • Child Friendly
                                    • Air conditioning

                                    Price per night from

                                    $346

                                    Price per night from

                                    $346

                                      35

                                      Walk to Lido Beach & Armand Cir, Wifi/DVD Included, Newly Renovated Corner Unit

                                      Southwest Gulf Coast / Sarasota

                                      Sarasota apartment

                                      2 5 min stay varies

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

                                      Price per night from

                                      $122

                                      Responds fast!
                                      avg. 4 minutes

                                      Price per night from

                                      $122

                                      (12) Excellent 

                                        16

                                        Midnight Cove: Living on the Water

                                        Southwest Gulf Coast / Sarasota

                                        Sarasota apartment

                                        2 5 min stay varies

                                        • 2 bedrooms
                                        • sleeps 5
                                        • min stay varies
                                        • Beach / lakeside relaxation
                                        • Swimming pool
                                        • Child Friendly
                                        “Having a fabulous time!!” This is our 2nd year in a row and plan on staying again next year. This is our favorite place by far. Fishing only yards from the Lanai, restaurants, stores, bait shop, gulf beach, all within a few minutes walk. The pool is
                                        …see more

                                        Price per night from

                                        $154

                                        Responds fast!
                                        avg. 2 hours 19 minutes

                                        Price per night from

                                        $154

                                        (1) Excellent 

                                          22

                                          Beautiful 3 bedms/2 bathms with pool close to Downtown

                                          Southwest Gulf Coast / Sarasota

                                          Sarasota house

                                          3 6 7 nights min

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

                                          Price per night from

                                          $200

                                          Price per night from

                                          $200

                                          (2) Very Good 

                                            19

                                            Walk to Crescent Beach, Upgraded Sea Winds Condo

                                            Southwest Gulf Coast / Sarasota

                                            Sarasota apartment

                                            2 4 7 nights min

                                            • 2 bedrooms
                                            • sleeps 4
                                            • 7 nights min
                                            • Beach / lakeside relaxation
                                            • Nearest beach 0 mi
                                            • Swimming pool

                                            Price per night from

                                            $132

                                            Responds fast!
                                            avg. 3 hours 34 minutes

                                            Price per night from

                                            $132

                                            (8) Very Good 

                                              9

                                              St.Armands Circle condo ( Kingston Arms )

                                              Southwest Gulf Coast / Sarasota

                                              Sarasota apartment

                                              2 6 7 nights min

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

                                              Price per night from

                                              $156

                                              Price per night from

                                              $156

                                              (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.
                                                …see more

                                                Price per night from

                                                $134

                                                Price per night from

                                                $134

                                                  5

                                                  Water Views on Siesta Key, Wifi, Close to Beach, Listen to the Waves Splash Gent

                                                  Southwest Gulf Coast / Sarasota

                                                  Sarasota apartment

                                                  3 6 min stay varies

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

                                                  Price per night from

                                                  $174

                                                  Responds fast!
                                                  avg. 4 minutes

                                                  Price per night from

                                                  $174

                                                    25

                                                    Well Appointed Home with Heated Pool Just Off Siesta Key Close Gulf Gate Area

                                                    Southwest Gulf Coast / Sarasota

                                                    Sarasota house

                                                    3 6 14 nights min

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

                                                    Price per night from

                                                    $262

                                                    Price per night from

                                                    $262

                                                    (19) Excellent 

                                                      11

                                                      bring A Boat, 12 Minutes To Sarasota Bay

                                                      Southwest Gulf Coast / Sarasota

                                                      Sarasota house

                                                      2 4 2 nights min

                                                      • 2 bedrooms
                                                      • sleeps 4
                                                      • 2 nights min
                                                      • Nearest beach 4 mi
                                                      • Swimming pool
                                                      • Air conditioning
                                                      “Great Spot: Helpful Host, Attractive Accommodations, Relaxing Hot Tub” Nestled within the first golfing/housing development in Florida (c. 1924),Whitfield Estates, Jim's renovated1960s house is an especially easy place to stay. It has a very large liv
                                                      …see more

                                                      Price per night from

                                                      $141

                                                      Responds fast!
                                                      avg. 1 hour 47 minutes

                                                      Price per night from

                                                      $141

                                                      (7) Excellent 

                                                      Certificate of Excellence

                                                        38

                                                        Heated pool home near Siesta Key

                                                        Southwest Gulf Coast / Sarasota

                                                        Sarasota house

                                                        2 6 min stay varies

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

                                                        Certificate of Excellence

                                                        Price per night from

                                                        $161

                                                        Responds fast!
                                                        avg. 1 hour 16 minutes

                                                        Price per night from

                                                        $161

                                                        (1) Excellent 

                                                          32

                                                          Sarasota's Shangri La for family getaways, weddings and more!

                                                          Southwest Gulf Coast / Sarasota

                                                          Sarasota house

                                                          3 10 min stay varies

                                                          • 3 bedrooms
                                                          • sleeps 10
                                                          • min stay varies
                                                          • Nearest beach 8 mi
                                                          • Swimming pool
                                                          • Child Friendly

                                                          Price per night from

                                                          $284

                                                          Responds fast!
                                                          avg. 2 hours 43 minutes

                                                          Price per night from

                                                          $284

                                                          (5) Very Good 

                                                            20

                                                            Sarasota exquisite vacation home

                                                            Southwest Gulf Coast / Sarasota

                                                            Sarasota house

                                                            3 8 29 nights min

                                                            • 3 bedrooms
                                                            • sleeps 8
                                                            • 29 nights min
                                                            • Beach / lakeside relaxation
                                                            • Nearest beach 7 mi
                                                            • Swimming pool
                                                            “Nice House in Sarasota” Stayed in this house in Sarasota. Its in a quiet neighbourhood which really suited us. The house was very clean and had lovely quality furnishings. Angel, the owner was excellent to deal with - responded very quickly to em
                                                            …see more

                                                            Price per night from

                                                            $211

                                                            Responds fast!
                                                            avg. 2 hours 15 minutes

                                                            Price per night from

                                                            $211

                                                            (2) Excellent 

                                                              27

                                                              Beautiful gated community near Siesta Key beach and downtown Sarasota

                                                              Southwest Gulf Coast / Sarasota

                                                              Sarasota house

                                                              2 4 5 nights min

                                                              • 2 bedrooms
                                                              • sleeps 4
                                                              • 5 nights min
                                                              • Swimming pool
                                                              • Air conditioning
                                                              • Private garden
                                                              “Great location and community” We loved our stay here. The location suited us. The community is clean and quiet. The people are friendly. Everything worked out for us, our first time renting. We would stay here again. Thank you.
                                                              …see more

                                                              Price per night from

                                                              $113

                                                              Responds fast!
                                                              avg. 3 hours 23 minutes

                                                              Price per night from

                                                              $113

                                                                18

                                                                Family Home, Heated Pool. 10 mins to #1 US Beach

                                                                Southwest Gulf Coast / Sarasota

                                                                Sarasota house

                                                                5 10 14 nights min

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

                                                                Price per night from

                                                                $241

                                                                Price per night from

                                                                $241

                                                                (10) Very Good 

                                                                  23

                                                                  Superb Village Des Pins Sarasota vacation villa near Siesta Key

                                                                  Southwest Gulf Coast / Sarasota

                                                                  Sarasota villa

                                                                  2 6 min stay varies

                                                                  • 2 bedrooms
                                                                  • sleeps 6
                                                                  • min stay varies
                                                                  • Beach / lakeside relaxation
                                                                  • Nearest beach 5 mi
                                                                  • Swimming pool
                                                                  “Nice stay in Sarasota” Eddie and Wendy great to deal with. Villa in great location. Very clean and comfortable. Excellent facilities in complex - beautiful heated pool and spa. Lovely grounds, very quiet and relaxing. Would recommend.
                                                                  …see more

                                                                  Price per night from

                                                                  $111

                                                                  Responds fast!
                                                                  avg. 57 minutes

                                                                  Price per night from

                                                                  $111

                                                                    53

                                                                    Crescent Beach Rental on Siesta Key, Sarasota, FL

                                                                    Southwest Gulf Coast / Sarasota

                                                                    Sarasota condo

                                                                    2 4 30 nights min

                                                                    • 2 bedrooms
                                                                    • sleeps 4
                                                                    • 30 nights min
                                                                    • Beach / lakeside relaxation
                                                                    • Swimming pool
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $137

                                                                    Price per night from

                                                                    $137

                                                                      36

                                                                      Gated Community with Free Wifi, Optional $250 Clubhouse Transfer for Golf and Ha

                                                                      Southwest Gulf Coast / Sarasota

                                                                      Sarasota apartment

                                                                      2 4 min stay varies

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

                                                                      Price per night from

                                                                      $67

                                                                      Responds fast!
                                                                      avg. 4 minutes

                                                                      Price per night from

                                                                      $67

                                                                        39

                                                                        New Rental: Dawson House "A kitchen that is truly warm at heart"

                                                                        Southwest Gulf Coast / Sarasota

                                                                        Sarasota house

                                                                        3 8 min stay varies

                                                                        • 3 bedrooms
                                                                        • sleeps 8
                                                                        • min stay varies
                                                                        • Nearest beach 5 mi
                                                                        • Swimming pool
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $264

                                                                        Responds fast!
                                                                        avg. 42 minutes

                                                                        Price per night from

                                                                        $264

                                                                        (14) Excellent 

                                                                          34

                                                                          Late SALE Sep/Oct only -Lakeside villa Uni. Park,golf,cycles,pool, beach

                                                                          Southwest Gulf Coast / Sarasota

                                                                          Sarasota villa

                                                                          3 4 30 nights min

                                                                          • 3 bedrooms
                                                                          • sleeps 4
                                                                          • 30 nights min
                                                                          • Beach / lakeside relaxation
                                                                          • Nearest beach 20 mi
                                                                          • Swimming pool
                                                                          “A perfect setting and location” Everything about this vacation is perfect from start to finish. Joyce guides you through the pre vacation procedure seamlessly. All relevant information is sent concerning local amenities and events occurring duri
                                                                          …see more

                                                                          Price per night from

                                                                          $210

                                                                          Responds fast!
                                                                          avg. 50 minutes

                                                                          Price per night from

                                                                          $210

                                                                            24

                                                                            Dog Friendly Heated Pool Home Close to Beaches & Town

                                                                            Southwest Gulf Coast / Sarasota

                                                                            Sarasota house

                                                                            3 6 min stay varies

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

                                                                            Price per night from

                                                                            $172

                                                                            Responds fast!
                                                                            avg. 1 hour 57 minutes

                                                                            Price per night from

                                                                            $172

                                                                              33

                                                                              Chinaberry 924 at Midnight Cove Siesta Key, FL.

                                                                              Southwest Gulf Coast / Sarasota

                                                                              Sarasota house

                                                                              2 6 min stay varies

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

                                                                              Price per night from

                                                                              $156

                                                                              Price per night from

                                                                              $156