Anna Maria Island cottages: Stay in luxury Anna Maria Island cottages with Holidaylettings.co.uk

Close

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

Filters applied: Cottage

68 cottages

(10) Excellent 

    53

    Holiday cottage in Bradenton Beach

    Anna Maria Island / Bradenton Beach

    3 8 min stay varies

    • 3 bedrooms
    • sleeps 8
    • min stay varies
    • Beach / lakeside relaxation
    • Child friendly
    • Car not necessary
    “Clean and modern in great location” Entire house recently renovated with modern appliances, central a/C, flat screen TV, dependable Wifi, unique design touches, cheery environment. Delightful owners very responsive. Young neighbors threw loud party while we were there. No idea if this is common. Twin beds designed more for children.

    from £96 / night

    £801 - £2,012 / week

    Book View

    from £96 / night

      25

      Bradenton Beach holiday cottage rental

      Anna Maria Island / Bradenton Beach

      1 4 min stay varies

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

      from £100 / night

      £664 - £823 / week

      Book View

      Responds fast!
      avg. 1 hour 30 minutes

      from £100 / night

      (6) Excellent 

        13

        Cottage rental in Holmes Beach

        Anna Maria Island / Holmes Beach

        2 6 4 nights min

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

        from £165 / night

        £1,044 / week

        Book View

        Responds fast!
        avg. 2 hours 16 minutes

        from £165 / night

        (1) Excellent 

          31

          Bradenton Beach holiday cottage rental

          Anna Maria Island / Bradenton Beach

          2 4 3 nights min

          • 2 bedrooms
          • sleeps 4
          • 3 nights min
          • Nearest beach 0 km
          • Child friendly
          • Car not necessary

          from £164 / night

          £1,035 - £2,555 / week

          Book View

          Responds fast!
          avg. 2 hours 57 minutes

          from £164 / night

          (2) Very Good 

            57

            Cottage rental in Bradenton Beach

            Anna Maria Island / Bradenton Beach

            4 15 7 nights min

            • 4 bedrooms
            • sleeps 15
            • 7 nights min
            • Beach / lakeside relaxation
            • Child friendly
            • Air conditioning

            from £118 / night

            £823 - £3,201 / week

            Book View

            from £118 / night

            (6) Excellent 

              31

              Bradenton Beach holiday cottage rental

              Anna Maria Island / Bradenton Beach

              2 6 min stay varies

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

              from £119 / night

              £827 / week

              Book View

              Responds fast!
              avg. 1 hour 45 minutes

              from £119 / night

              (2) Excellent 

                22

                Holmes Beach holiday cottage let

                Anna Maria Island / Holmes Beach

                2 6 4 nights min

                • 2 bedrooms
                • sleeps 6
                • 4 nights min
                • Beach / lakeside relaxation
                • Nearest beach 0.02 km
                • Swimming pool

                from £182 / night

                £1,189 / week

                Book View

                Responds fast!
                avg. 1 hour 17 minutes

                from £182 / night

                (2) Excellent 

                  31

                  Holiday cottage with swimming pool in Holmes Beach

                  Anna Maria Island / Holmes Beach

                  3 6 30 nights min

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

                  from £206 / night

                  £1,134 / week

                  Book View

                  from £206 / night

                  (1) Excellent 

                    21

                    Cottage rental in Anna Maria

                    Anna Maria Island / Anna Maria

                    2 4 min stay varies

                    • 2 bedrooms
                    • sleeps 4
                    • min stay varies
                    • Beach / lakeside relaxation
                    • Child friendly
                    • Air conditioning

                    from £173 / night

                    £1,212 / week

                    Book View

                    from £173 / night

                    (9) Very Good 

                    Certificate of Excellence

                      16

                      Holiday cottage in Anna Maria

                      Anna Maria Island / Anna Maria

                      3 6 min stay varies

                      • 3 bedrooms
                      • sleeps 6
                      • min stay varies
                      • Child friendly
                      • Air conditioning
                      • Private garden

                      Certificate of Excellence

                      from £182 / night

                      £1,274 / week

                      Book View

                      from £182 / night

                        12

                        Holiday cottage in Holmes Beach

                        Anna Maria Island / Holmes Beach

                        2 4 4 nights min

                        • 2 bedrooms
                        • sleeps 4
                        • 4 nights min
                        • Beach / lakeside relaxation
                        • Child friendly
                        • Car not necessary

                        from £165 / night

                        £1,044 / week

                        Book View

                        Responds fast!
                        avg. 2 hours 16 minutes

                        from £165 / night

                          13

                          Cottage rental in Bradenton Beach

                          Anna Maria Island / Bradenton Beach

                          1 2 min stay varies

                          • 1 bedroom
                          • sleeps 2
                          • min stay varies

                          from £87 / night

                          £579 - £671 / week

                          Book View

                          Responds fast!
                          avg. 1 hour 30 minutes

                          from £87 / night

                            12

                            Cottage rental in Holmes Beach

                            Anna Maria Island / Holmes Beach

                            1 5 7 nights min

                            • 1 bedroom
                            • sleeps 5
                            • 7 nights min
                            • Ask owner if suitable for children
                            • Air conditioning

                            from £58 / night

                            £404 / week

                            Book View

                            Responds fast!
                            avg. 2 hours 56 minutes

                            from £58 / night

                            (1) Excellent 

                              19

                              Holiday cottage rental

                              Anna Maria Island / Bradenton Beach

                              1 4 min stay varies

                              • 1 bedroom
                              • sleeps 4
                              • min stay varies

                              from £104 / night

                              £689 - £824 / week

                              Book View

                              Responds fast!
                              avg. 1 hour 30 minutes

                              from £104 / night

                                15

                                Holiday cottage in Bradenton Beach

                                Anna Maria Island / Bradenton Beach

                                1 2 min stay varies

                                • 1 bedroom
                                • sleeps 2
                                • min stay varies

                                from £83 / night

                                £548 - £700 / week

                                Book View

                                Responds fast!
                                avg. 1 hour 30 minutes

                                from £83 / night

                                  26

                                  Bradenton Beach holiday cottage rental

                                  Anna Maria Island / Bradenton Beach

                                  1 4 3 nights min

                                  • 1 bedroom
                                  • sleeps 4
                                  • 3 nights min

                                  from £110 / night

                                  £731 - £823 / week

                                  Book View

                                  Responds fast!
                                  avg. 1 hour 30 minutes

                                  from £110 / night

                                    20

                                    Holiday cottage rental

                                    Anna Maria Island / Bradenton Beach

                                    1 2 3 nights min

                                    • 1 bedroom
                                    • sleeps 2
                                    • 3 nights min
                                    • Child friendly

                                    from £91 / night

                                    £571 - £692 / week

                                    Book View

                                    Responds fast!
                                    avg. 1 hour 30 minutes

                                    from £91 / night

                                    (1)  

                                      5

                                      Holiday cottage in Bradenton Beach

                                      Anna Maria Island / Bradenton Beach

                                      2 7 7 nights min

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

                                      from £158 / night

                                      £1,101 / week

                                      Book View

                                      from £158 / night

                                      Great rentals within 20 miles that match your search

                                      Distance approx 19.5 miles from Anna Maria Island

                                      (1) Very Good 

                                        32

                                        Holiday cottage with swimming pool in Sarasota

                                        Southwest Gulf Coast / Sarasota

                                        1 2 7 nights min

                                        • 1 bedroom
                                        • sleeps 2
                                        • 7 nights min
                                        • Nearest beach 0.1 km
                                        • Swimming pool
                                        • Ask owner if suitable for children

                                        from £341 / night

                                        £2,386 / week

                                        Book View

                                        from £341 / night

                                        Distance approx 18.39 miles from Anna Maria Island

                                        (2) Excellent 

                                          11

                                          Madeira Beach holiday cottage rental

                                          Florida / Madeira Beach

                                          1 2 min stay varies

                                          • 1 bedroom
                                          • sleeps 2
                                          • min stay varies
                                          • Beach / lakeside relaxation
                                          • Child friendly

                                          from £138 / night

                                          £1,028 / week

                                          Book View

                                          from £138 / night

                                          Distance approx 18.39 miles from Anna Maria Island

                                            24

                                            Madeira Beach holiday cottage rental

                                            Florida / Madeira Beach

                                            1 2 min stay varies

                                            • 1 bedroom
                                            • sleeps 2
                                            • min stay varies
                                            • Swimming pool
                                            • Air conditioning
                                            • Ask about pets

                                            from £138 / night

                                            £1,028 / week

                                            Book View

                                            from £138 / night

                                            Distance approx 19.8 miles from Anna Maria Island

                                              8

                                              Holiday cottage letting

                                              Southwest Gulf Coast / Sarasota

                                              1 2 1 night min

                                              • 1 bedroom
                                              • sleeps 2
                                              • 1 night min
                                              • Child friendly
                                              • Air conditioning
                                              • Private garden

                                              from £69 / night

                                              £480 / week

                                              Book View

                                              Responds fast!
                                              avg. 25 minutes

                                              from £69 / night

                                              Distance approx 14.75 miles from Anna Maria Island

                                                20

                                                St. Pete Beach holiday cottage rental

                                                Florida / St. Pete Beach

                                                1 3 3 nights min

                                                • 1 bedroom
                                                • sleeps 3
                                                • 3 nights min
                                                • Child friendly
                                                • Air conditioning

                                                from £126 / night

                                                £877 / week

                                                Book View

                                                Responds fast!
                                                avg. 1 hour 7 minutes

                                                from £126 / night

                                                Distance approx 11.85 miles from Anna Maria Island

                                                  26

                                                  St. Pete Beach holiday cottage rental

                                                  St. Pete Beach / Pass-a-Grille

                                                  2 6 1 night min

                                                  • 2 bedrooms
                                                  • sleeps 6
                                                  • 1 night min
                                                  • Beach / lakeside relaxation
                                                  • Nearest beach 1 km
                                                  • Child friendly

                                                  from £229 / night

                                                  £1,341 / week

                                                  Book View

                                                  from £229 / night

                                                  Distance approx 11.82 miles from Anna Maria Island

                                                    16

                                                    Holiday cottage in St. Pete Beach

                                                    Florida / St. Pete Beach

                                                    1 4 1 night min

                                                    • 1 bedroom
                                                    • sleeps 4
                                                    • 1 night min
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 1 km
                                                    • Child friendly

                                                    from £128 / night

                                                    £794 / week

                                                    Book View

                                                    from £128 / night

                                                    Distance approx 17.53 miles from Anna Maria Island

                                                    (5) Excellent 

                                                      20

                                                      Cottage rental in Treasure Island

                                                      Florida / Treasure Island

                                                      2 5 3 nights min

                                                      • 2 bedrooms
                                                      • sleeps 5
                                                      • 3 nights min
                                                      • Beach / lakeside relaxation
                                                      • Nearest beach 0 km
                                                      • Child friendly

                                                      from £170 / night

                                                      £1,191 / week

                                                      Book View

                                                      from £170 / night

                                                      Distance approx 18.96 miles from Anna Maria Island

                                                      (3) Excellent 

                                                        61

                                                        Holiday cottage in Madeira Beach

                                                        Florida / Madeira Beach

                                                        2 6 3 nights min

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • 3 nights min
                                                        • Nearest beach 1 km
                                                        • Swimming pool
                                                        • Child friendly

                                                        from £146 / night

                                                        £1,018 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 1 hour 35 minutes

                                                        from £146 / night

                                                        Distance approx 18.39 miles from Anna Maria Island

                                                          25

                                                          Madeira Beach holiday cottage rental

                                                          Florida / Madeira Beach

                                                          1 2 min stay varies

                                                          • 1 bedroom
                                                          • sleeps 2
                                                          • min stay varies
                                                          • Beach / lakeside relaxation
                                                          • Swimming pool
                                                          • Air conditioning

                                                          from £138 / night

                                                          £1,025 / week

                                                          Book View

                                                          from £138 / night

                                                          Distance approx 11.84 miles from Anna Maria Island

                                                            26

                                                            St. Pete Beach holiday cottage rental

                                                            Florida / St. Pete Beach

                                                            1 4 1 night min

                                                            • 1 bedroom
                                                            • sleeps 4
                                                            • 1 night min
                                                            • Beach / lakeside relaxation
                                                            • Child friendly
                                                            • Car not necessary

                                                            from £149 / night

                                                            £917 / week

                                                            Book View

                                                            from £149 / night

                                                            Distance approx 11.32 miles from Anna Maria Island

                                                            (3) Very Good 

                                                              16

                                                              Holiday cottage in St. Pete Beach

                                                              Florida / St. Pete Beach

                                                              1 4 1 night min

                                                              • 1 bedroom
                                                              • sleeps 4
                                                              • 1 night min
                                                              • Beach / lakeside relaxation
                                                              • Nearest beach 1 km
                                                              • Child friendly

                                                              from £133 / night

                                                              £794 / week

                                                              Book View

                                                              from £133 / night

                                                              Distance approx 18.99 miles from Anna Maria Island

                                                              (8) Excellent 

                                                              Certificate of Excellence

                                                                23

                                                                Cottage accommodation in Madeira Beach

                                                                Florida / Madeira Beach

                                                                4 3 nights min

                                                                • sleeps 4
                                                                • 3 nights min
                                                                • Swimming pool
                                                                • Child friendly
                                                                • Air conditioning

                                                                Certificate of Excellence

                                                                from £69 / night

                                                                £412 - £458 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 34 minutes

                                                                from £69 / night

                                                                Distance approx 18.73 miles from Anna Maria Island

                                                                  24

                                                                  Holiday cottage in Sarasota

                                                                  Southwest Gulf Coast / Sarasota

                                                                  1 2 30 nights min

                                                                  • 1 bedroom
                                                                  • sleeps 2
                                                                  • 30 nights min
                                                                  • Air conditioning

                                                                  from £92 / night

                                                                  £641 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 33 minutes

                                                                  from £92 / night

                                                                  Distance approx 18.94 miles from Anna Maria Island

                                                                  (1) Excellent 

                                                                    4

                                                                    Madeira Beach holiday cottage rental

                                                                    Florida / Madeira Beach

                                                                    1 2 3 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 2
                                                                    • 3 nights min
                                                                    • Nearest beach 0.01 km
                                                                    • Swimming pool
                                                                    • Car not necessary

                                                                    from £74 / night

                                                                    £458 / week

                                                                    Book View

                                                                    from £74 / night

                                                                    Distance approx 17.66 miles from Anna Maria Island

                                                                      26

                                                                      Cottage rental in St. Petersburg

                                                                      Florida / St. Petersburg

                                                                      3 6 min stay varies

                                                                      • 3 bedrooms
                                                                      • sleeps 6
                                                                      • min stay varies
                                                                      • Child friendly
                                                                      • Air conditioning

                                                                      from £151 / night

                                                                      £1,058 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 33 minutes

                                                                      from £151 / night

                                                                      Distance approx 15.94 miles from Anna Maria Island

                                                                        24

                                                                        Cottage rental in St. Petersburg

                                                                        Florida / St. Petersburg

                                                                        1 4 2 nights min

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

                                                                        from £83 / night

                                                                        £577 / week

                                                                        Book View

                                                                        Responds fast!
                                                                        avg. 33 minutes

                                                                        from £83 / night

                                                                        Distance approx 9.44 miles from Anna Maria Island

                                                                          32

                                                                          Holiday cottage in Palmetto

                                                                          Florida / Palmetto

                                                                          3 7 2 nights min

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

                                                                          from £119 / night

                                                                          £649 / week

                                                                          Book View

                                                                          from £119 / night

                                                                          Distance approx 17.46 miles from Anna Maria Island

                                                                            25

                                                                            Cottage accommodation in Treasure Island

                                                                            Florida / Treasure Island

                                                                            1 4 3 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • 3 nights min
                                                                            • Child friendly
                                                                            • Air conditioning
                                                                            • Pet friendly

                                                                            from £83 / night

                                                                            £577 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 33 minutes

                                                                            from £83 / night

                                                                            Distance approx 17.46 miles from Anna Maria Island

                                                                              25

                                                                              Holiday cottage rental

                                                                              Florida / Treasure Island

                                                                              2 4 3 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • 3 nights min
                                                                              • Child friendly
                                                                              • Air conditioning
                                                                              • Pet friendly

                                                                              from £97 / night

                                                                              £673 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 33 minutes

                                                                              from £97 / night

                                                                              Distance approx 4.79 miles from Anna Maria Island Show on Map

                                                                                24

                                                                                Holiday cottage in Cortez

                                                                                Florida / Cortez

                                                                                2 4 5 nights min

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

                                                                                from £92 / night

                                                                                £641 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 33 minutes

                                                                                from £92 / night

                                                                                Distance approx 9.44 miles from Anna Maria Island

                                                                                  13

                                                                                  Longboat Key holiday cottage rental

                                                                                  Florida / Longboat Key

                                                                                  1 4 7 nights min

                                                                                  • 1 bedroom
                                                                                  • sleeps 4
                                                                                  • 7 nights min
                                                                                  • Swimming pool
                                                                                  • Child friendly
                                                                                  • Air conditioning

                                                                                  from £115 / night

                                                                                  £802 / week

                                                                                  Book View

                                                                                  from £115 / night

                                                                                  Also consider