Beach rentals in Siesta Key and Villas - Holiday Lettings - Holiday Rentals Siesta Key

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2,442 Holiday homes

(30) Excellent 

    28

    Siesta Key holiday condo rental

    Florida / Siesta Key

    2 5 7 nights min

    • 2 bedrooms
    • sleeps 5
    • 7 nights min
    • Beach / lakeside relaxation
    • Nearest beach 0.01 km
    • Swimming pool

    from £317 / night

    £2,217 / week

    Book View

    Responds fast!
    avg. 30 minutes

    from £317 / night

    (2) Excellent 

      26

      Holiday villa in Siesta Key

      Florida / Siesta Key

      4 8 min stay varies

      • 4 bedrooms
      • sleeps 8
      • min stay varies
      • Beach / lakeside relaxation
      • Swimming pool
      • Child friendly

      from £179 / night

      £896 - £2,088 / week

      Book View

      Responds fast!
      avg. 40 minutes

      from £179 / night

      (1) Excellent 

        24

        Home rental in Siesta Key with swimming pool

        Florida / Siesta Key

        3 6 14 nights min

        • 3 bedrooms
        • sleeps 6
        • 14 nights min
        • Beach / lakeside relaxation
        • Nearest beach 0.8 km
        • Swimming pool

        from £171 / night

        £1,197 / week

        Book View

        Responds fast!
        avg. 2 hours 57 minutes

        from £171 / night

          30

          Holiday condo in Siesta Key

          Florida / Siesta Key

          2 5 14 nights min

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

          from £102 / night

          £710 / week

          Book View

          from £102 / night

          (1) Excellent 

            38

            Holiday townhouse in Siesta Key

            Florida / Siesta Key

            2 6 min stay varies

            • 2 bedrooms
            • sleeps 6
            • min stay varies
            • Beach / lakeside relaxation
            • Nearest beach 0.1 km
            • Swimming pool

            from £209 / night

            £1,330 - £2,217 / week

            Book View

            Responds fast!
            avg. 3 hours 42 minutes

            from £209 / night

            (24) Excellent 

              16

              Siesta Key holiday apartment rental

              Florida / Siesta Key

              2 5 min stay varies

              • 2 bedrooms
              • sleeps 5
              • min stay varies
              • Beach / lakeside relaxation
              • Nearest beach 1 km
              • Child friendly

              from £138 / night

              £887 - £1,503 / week

              Book View

              Responds fast!
              avg. 1 hour 28 minutes

              from £138 / night

              (4) Excellent 

                14

                Siesta Key holiday home rental

                Florida / Siesta Key

                1 4 min stay varies

                • 1 bedroom
                • sleeps 4
                • min stay varies
                • Nearest beach 0.32 km
                • Child friendly
                • Air conditioning

                from £115 / night

                £801 / week

                Book View

                from £115 / night

                (4) Excellent 

                  12

                  Holiday apartment in Siesta Key

                  Florida / Siesta Key

                  2 6 1 night min

                  • 2 bedrooms
                  • sleeps 6
                  • 1 night min
                  • Beach / lakeside relaxation
                  • Swimming pool
                  • Child friendly

                  from £223 / night

                  £1,558 / week

                  Book View

                  Responds fast!
                  avg. 1 hour 50 minutes

                  from £223 / night

                    58

                    Condo rental in Siesta Key

                    Florida / Siesta Key

                    2 6 7 nights min

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

                    from £186 / night

                    £1,297 / week

                    Book View

                    from £186 / night

                      36

                      Siesta Key holiday apartment rental

                      Florida / Siesta Key

                      2 4 min stay varies

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

                      from £168 / night

                      £807 - £1,175 / week

                      Book View

                      Responds fast!
                      avg. 4 minutes

                      from £168 / night

                        25

                        Holiday townhouse in Siesta Key

                        Florida / Siesta Key

                        2 4 7 nights min

                        • 2 bedrooms
                        • sleeps 4
                        • 7 nights min
                        • Child friendly
                        • Air conditioning

                        from £186 / night

                        £1,297 / week

                        Book View

                        from £186 / night

                          36

                          Holiday apartment in Siesta Key

                          Florida / Siesta Key

                          2 6 7 nights min

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

                          from £95 / night

                          £640 - £1,353 / week

                          Book View

                          Responds fast!
                          avg. 4 minutes

                          from £95 / night

                          (18) Very Good 

                            24

                            Holiday townhouse in Siesta Key

                            Florida / Siesta Key

                            1 4 min stay varies

                            • 1 bedroom
                            • sleeps 4
                            • min stay varies
                            • Beach / lakeside relaxation
                            • Swimming pool
                            • Child friendly

                            from £167 / night

                            £1,167 / week

                            Book View

                            Responds fast!
                            avg. 2 hours 8 minutes

                            from £167 / night

                              46

                              Holiday home with swimming pool in Siesta Key

                              Florida / Siesta Key

                              4 8 min stay varies

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

                              from £222 / night

                              £1,552 / week

                              Book View

                              Responds fast!
                              avg. 4 minutes

                              from £222 / night

                              (3) Excellent 

                                10

                                Holiday condo in Siesta Key

                                Florida / Siesta Key

                                2 6 7 nights min

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

                                from £108 / night

                                £798 / week

                                Book View

                                from £108 / night

                                (15) Very Good 

                                  32

                                  Siesta Key holiday cottage rental

                                  Florida / Siesta Key

                                  1 2 3 nights min

                                  • 1 bedroom
                                  • sleeps 2
                                  • 3 nights min
                                  • Beach / lakeside relaxation
                                  • Nearest beach 0.1 km
                                  • Child friendly

                                  from £79 / night

                                  £553 / week

                                  Book View

                                  Responds fast!
                                  avg. 1 hour 40 minutes

                                  from £79 / night

                                    14

                                    Holiday cottage in Siesta Key

                                    Florida / Siesta Key

                                    1 4 min stay varies

                                    • 1 bedroom
                                    • sleeps 4
                                    • min stay varies
                                    • Child friendly
                                    • Pet friendly

                                    from £150 / night

                                    £1,049 / week

                                    Book View

                                    from £150 / night

                                    (23) Very Good 

                                      40

                                      Home rental in Siesta Key

                                      Florida / Siesta Key

                                      2 6 3 nights min

                                      • 2 bedrooms
                                      • sleeps 6
                                      • 3 nights min
                                      • Beach / lakeside relaxation
                                      • Nearest beach 0 km
                                      • Swimming pool

                                      from £266 / night

                                      £1,330 - £1,862 / week

                                      Book View

                                      Responds fast!
                                      avg. 52 minutes

                                      from £266 / night

                                      (3) Excellent 

                                        45

                                        Siesta Key holiday condo rental

                                        Florida / Siesta Key

                                        2 6 min stay varies

                                        • 2 bedrooms
                                        • sleeps 6
                                        • min stay varies
                                        • Swimming pool
                                        • Child friendly
                                        • Car not necessary

                                        from £83 / night

                                        £577 - £1,153 / week

                                        Book View

                                        Responds fast!
                                        avg. 2 hours 22 minutes

                                        from £83 / night

                                        (13) Excellent 

                                          59

                                          Siesta Key holiday apartment rental

                                          Florida / Siesta Key

                                          2 6 7 nights min

                                          • 2 bedrooms
                                          • sleeps 6
                                          • 7 nights min
                                          • Beach / lakeside relaxation
                                          • Swimming pool
                                          • Child friendly

                                          from £140 / night

                                          £980 - £2,035 / week

                                          Book View

                                          Responds fast!
                                          avg. 3 hours 15 minutes

                                          from £140 / night

                                          (2) Average 

                                            42

                                            Siesta Key holiday condo let

                                            Florida / Siesta Key

                                            2 5 min stay varies

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

                                            from £144 / night

                                            £900 - £2,054 / week

                                            Book View

                                            Responds fast!
                                            avg. 4 minutes

                                            from £144 / night

                                              19

                                              Holiday apartment in Siesta Key

                                              Florida / Siesta Key

                                              3 8 7 nights min

                                              • 3 bedrooms
                                              • sleeps 8
                                              • 7 nights min
                                              • Swimming pool
                                              • Child friendly
                                              • Car not necessary

                                              from £141 / night

                                              £987 / week

                                              Book View

                                              from £141 / night

                                                16

                                                Holiday villa in Siesta Key

                                                Florida / Siesta Key

                                                2 6 min stay varies

                                                • 2 bedrooms
                                                • sleeps 6
                                                • min stay varies
                                                • Child friendly

                                                from £186 / night

                                                £1,297 / week

                                                Book View

                                                from £186 / night

                                                (5) Very Good 

                                                  42

                                                  Holiday condo with swimming pool in Siesta Key

                                                  Florida / Siesta Key

                                                  2 5 6 nights min

                                                  • 2 bedrooms
                                                  • sleeps 5
                                                  • 6 nights min
                                                  • Swimming pool
                                                  • Child friendly
                                                  • Air conditioning

                                                  from £93 / night

                                                  £646 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 2 hours 45 minutes

                                                  from £93 / night

                                                    31

                                                    Holiday home in Siesta Key

                                                    Florida / Siesta Key

                                                    2 4 7 nights min

                                                    • 2 bedrooms
                                                    • sleeps 4
                                                    • 7 nights min
                                                    • Swimming pool
                                                    • Child friendly
                                                    • Air conditioning

                                                    from £417 / night

                                                    £2,917 / week

                                                    Book View

                                                    from £417 / night

                                                    (1) Excellent 

                                                      36

                                                      Holiday home with swimming pool in Siesta Key

                                                      Florida / Siesta Key

                                                      4 6 min stay varies

                                                      • 4 bedrooms
                                                      • sleeps 6
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Child friendly
                                                      • Air conditioning

                                                      from £225 / night

                                                      £1,241 - £2,036 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 4 minutes

                                                      from £225 / night

                                                      (1)  

                                                        32

                                                        Siesta Key holiday apartment rental

                                                        Florida / Siesta Key

                                                        2 6 min stay varies

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

                                                        from £96 / night

                                                        £710 - £1,229 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 4 minutes

                                                        from £96 / night

                                                        (16) Excellent 

                                                          21

                                                          Siesta Key holiday apartment rental

                                                          Florida / Siesta Key

                                                          3 7 min stay varies

                                                          • 3 bedrooms
                                                          • sleeps 7
                                                          • min stay varies
                                                          • Beach / lakeside relaxation
                                                          • Nearest beach 1 km
                                                          • Child friendly

                                                          from £177 / night

                                                          £1,175 - £1,862 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 1 hour 28 minutes

                                                          from £177 / night

                                                          (4) Excellent 

                                                          Certificate of Excellence

                                                            36

                                                            Apartment rental in Siesta Key with shared pool

                                                            Florida / Siesta Key

                                                            2 6 7 nights min

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

                                                            Certificate of Excellence

                                                            from £125 / night

                                                            £801 - £1,819 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 4 minutes

                                                            from £125 / night

                                                            (1) Excellent 

                                                              42

                                                              Siesta Key holiday home rental

                                                              Florida / Siesta Key

                                                              3 8 min stay varies

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

                                                              from £125 / night

                                                              £944 - £1,601 / week

                                                              Book View

                                                              Responds fast!
                                                              avg. 4 minutes

                                                              from £125 / night

                                                                36

                                                                Apartment rental in Siesta Key with shared pool

                                                                Florida / Siesta Key

                                                                2 4 14 nights min

                                                                • 2 bedrooms
                                                                • sleeps 4
                                                                • 14 nights min
                                                                • Swimming pool
                                                                • Child friendly
                                                                • Air conditioning

                                                                from £115 / night

                                                                £652 - £1,186 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 4 minutes

                                                                from £115 / night

                                                                (7) Very Good 

                                                                  26

                                                                  Siesta Key holiday villa rental

                                                                  Florida / Siesta Key

                                                                  2 6 min stay varies

                                                                  • 2 bedrooms
                                                                  • sleeps 6
                                                                  • min stay varies
                                                                  • Beach / lakeside relaxation
                                                                  • Nearest beach 0.2 km
                                                                  • Swimming pool

                                                                  from £160 / night

                                                                  £1,507 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 3 hours 3 minutes

                                                                  from £160 / night

                                                                  (5) Very Good 

                                                                    36

                                                                    Siesta Key holiday apartment rental

                                                                    Florida / Siesta Key

                                                                    2 6 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 6
                                                                    • min stay varies
                                                                    • Beach / lakeside relaxation
                                                                    • Nearest beach 0.2 km
                                                                    • Swimming pool

                                                                    from £89 / night

                                                                    £621 - £1,153 / week

                                                                    Book View

                                                                    from £89 / night

                                                                    (2) Very Good 

                                                                      24

                                                                      Siesta Key holiday apartment rental

                                                                      Florida / Siesta Key

                                                                      1 4 min stay varies

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

                                                                      from £95 / night

                                                                      £664 - £1,255 / week

                                                                      Book View

                                                                      from £95 / night

                                                                      (5) Excellent 

                                                                        47

                                                                        Holiday villa rental

                                                                        Florida / Siesta Key

                                                                        2 6 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 6
                                                                        • min stay varies
                                                                        • Beach / lakeside relaxation
                                                                        • Nearest beach 0.1 km
                                                                        • Swimming pool

                                                                        from £136 / night

                                                                        £950 / week

                                                                        Book View

                                                                        Responds fast!
                                                                        avg. 2 hours 12 minutes

                                                                        from £136 / night

                                                                        (12) Excellent 

                                                                        Certificate of Excellence

                                                                          50

                                                                          Hotel apartment rental in Siesta Key

                                                                          Florida / Siesta Key

                                                                          3 6 7 nights min

                                                                          • 3 bedrooms
                                                                          • sleeps 6
                                                                          • 7 nights min
                                                                          • Beach / lakeside relaxation
                                                                          • Swimming pool
                                                                          • Child friendly

                                                                          Certificate of Excellence

                                                                          from £191 / night

                                                                          £1,335 - £1,769 / week

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 1 hour 0 minutes

                                                                          from £191 / night

                                                                            36

                                                                            Siesta Key holiday condo rental

                                                                            Florida / Siesta Key

                                                                            1 4 min stay varies

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

                                                                            from £135 / night

                                                                            £689 - £1,521 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 4 minutes

                                                                            from £135 / night

                                                                              40

                                                                              Siesta Key holiday villa rental

                                                                              Florida / Siesta Key

                                                                              2 6 7 nights min

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

                                                                              from £177 / night

                                                                              £1,235 / week

                                                                              Book View

                                                                              from £177 / night

                                                                              (21) Excellent 

                                                                              Certificate of Excellence

                                                                                42

                                                                                Home rental in Siesta Key

                                                                                Florida / Siesta Key

                                                                                1 4 3 nights min

                                                                                • 1 bedroom
                                                                                • sleeps 4
                                                                                • 3 nights min
                                                                                • Beach / lakeside relaxation
                                                                                • Nearest beach 0.1 km
                                                                                • Child friendly

                                                                                Certificate of Excellence

                                                                                from £79 / night

                                                                                £553 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 2 hours 23 minutes

                                                                                from £79 / night

                                                                                  32

                                                                                  Siesta Key holiday apartment rental

                                                                                  Florida / Siesta Key

                                                                                  2 8 7 nights min

                                                                                  • 2 bedrooms
                                                                                  • sleeps 8
                                                                                  • 7 nights min
                                                                                  • Child friendly
                                                                                  • Pet friendly

                                                                                  from £186 / night

                                                                                  £1,297 / week

                                                                                  Book View

                                                                                  from £186 / night

                                                                                  Top Destination reviews

                                                                                  2/2 Ground Floor Condo with Patio on Intracoastal
                                                                                  Siesta Key Condo

                                                                                  Condo is beautifully situated on instracoastal shoreline on Siesta Key looking out to Sarasota on mainland. It takes approximately 10 min to walk on to the stunning beach looking out to Mexican Gulf. The condo itself was spotless and had all the amenities required to make our stay so enjoyable. The patio with table, chairs and hammock were a welcome bonus and allowed to appreciate the beautiful surroundings without having to leave the condo !!! Since the original booking, the owner has been easily contactable and responsive with any questions we had prior to our arrival. Great value for money and would not hesitate to rebook for future visits.see more
                                                                                  Siesta Key 3 Bdrm Private House with Heated Pool minutes from village and beach
                                                                                  Mr

                                                                                  My wife and I enjoyed the most wonderful holiday in this excellent villa. It was very comfortable, had everything we needed and more, and is perfectly situated for the beaches and Siesta Key village is a short walk or bike ride away. The pool was a great bonus. All together, this was a great holiday.see more
                                                                                  Remodeled 2br 2ba with private patio, beautiful water views, walk to #1 beach
                                                                                  Paradise

                                                                                  The apt is very well appointed and spacious. Ruth is very amenable and easy to get in touch with. Having a land line so that family could contact us was a great bonus. Saved us using our u.k. mobile which can be very expensive.. local calls are free. We visit siesta every year for a month and this is one of the best places we have stayed.. close to the wonderful beach. The pool area Iis very picturesque . This with the unique siesta village nightlife. Makes it a perfect place for all ages Thanks Ruthsee more
                                                                                  Siesta Key - 2bdrm on the beach - amazing views!!
                                                                                  Awesome place! Comforts of home, but with an amazing view!!!

                                                                                  Loved our stay. Very comfortable beach getaway. Everything we needed was here. Great sunsets, beach, and pool. Saw two manatee, lots of pelican, and one turtle. The lanai overlooking the beach and water was a real hit! Would definitely stay again! … see more

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