Vacation Rentals with Pool in Holmes Beach

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Filtering by: Swimming pool

2,037 vacation rentals
    18

    runaway bay 2 bedroom condo with wonderful access to restaurant, beach, shopping

    Anna Maria Island / Holmes Beach

    Holmes Beach apartment

    2 6 30 nights min

    • 2 bedrooms
    • sleeps 6
    • 30 nights min
    • Nearest beach 1 mi
    • Swimming pool
    • Car not necessary

    Price per night from

    $176

    Price per night from

    $176

    (9) Very Good 

      31

      Anna Maria Island, 2 Bed, 2 Bath Condo in quiet setting near to Beaches

      Anna Maria Island / Holmes Beach

      Holmes Beach condo

      2 4 7 nights min

      • 2 bedrooms
      • sleeps 4
      • 7 nights min
      • Beach / lakeside relaxation
      • Nearest beach 0.8 mi
      • Swimming pool
      “Beautiful condo, close to everything!” Everything was perfect in the condo which was new and updated! The 2 new full size beds in the 2nd bedroom were too hard. The pool was a nice size and stayed sunny most of the day. Shopping was close and the c
      …see more

      Price per night from

      $105

      Price per night from

      $105

      (47) Excellent 

        22

        Gulf Beach Place - Just a few steps from the Beach

        Anna Maria Island / Holmes Beach

        Holmes Beach condo

        2 6 min stay varies

        • 2 bedrooms
        • sleeps 6
        • min stay varies
        • Beach / lakeside relaxation
        • Nearest beach 0 mi
        • Swimming pool
        “Another Fantastic Stay” This is my second time staying at Kay’s Gulf Place Condo! Very clean, comfortable and charming! Location has it all! Sunsets from the rooftop deck are to die for! No detail missed!
        …see more

        Price per night from

        $120

        Responds fast!
        avg. 2 hours 31 minutes

        Price per night from

        $120

        (4) Excellent 

          22

          Cozy Cabana West - Private Pool - Close to Beach

          Anna Maria Island / Holmes Beach

          Holmes Beach villa

          2 6 min stay varies

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

          Price per night from

          $185

          Responds fast!
          avg. 2 hours 32 minutes

          Price per night from

          $185

          (9) Excellent 

            26

            Blue Bayou

            Anna Maria Island / Holmes Beach

            Holmes Beach apartment

            2 6 min stay varies

            • 2 bedrooms
            • sleeps 6
            • min stay varies
            • Swimming pool
            • Child Friendly
            • Air conditioning
            “"Home from Home"” A very well appointed apartment in a great location that had everything you would wish for to enhance your vacation experience. A real home from home that is clean, well furnished and spacious. The owners have been great to deal wi
            …see more

            Price per night from

            $143

            Price per night from

            $143

              29

              Pet-Friendly Holmes Beach Home - Steps to Beach!

              Anna Maria Island / Holmes Beach

              Holmes Beach house

              3 6 7 nights min

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

              Price per night from

              $296

              Responds fast!
              avg. 36 minutes

              Price per night from

              $296

                54

                Professionally decorated home w/ private pool, 2 blocks from beach! Dogs OK!

                Anna Maria Island / Holmes Beach

                Holmes Beach house

                3 6 7 nights min

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

                Price per night from

                $241

                Responds fast!
                avg. 1 hour 58 minutes

                Price per night from

                $241

                (31) Excellent 

                Certificate of Excellence

                  52

                  Happy Island Cottage with heated private Pool

                  Anna Maria Island / Holmes Beach

                  Holmes Beach house

                  3 8 6 nights min

                  • 3 bedrooms
                  • sleeps 8
                  • 6 nights min
                  • Beach / lakeside relaxation
                  • Swimming pool
                  • Child Friendly
                  “Exceeded expectations!” For several years, I've wanted to spend Christmas on AMI with my family. This past Christmas, I was able to do that, and we stayed at Happy Island Cottage. This was a wonderful house to stay in, and Alex was great and very re
                  …see more

                  Certificate of Excellence

                  Price per night from

                  $308

                  Responds fast!
                  avg. 2 hours 13 minutes

                  Price per night from

                  $308

                    35

                    Mediterranean-style home w/ private pool, jetted tub, and easy beach access!

                    Anna Maria Island / Holmes Beach

                    Holmes Beach house

                    2 6 7 nights min

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

                    Price per night from

                    $170

                    Responds fast!
                    avg. 1 hour 58 minutes

                    Price per night from

                    $170

                    (5) Average 

                      26

                      Anthony Beach Cottages Island Retreat

                      Anna Maria Island / Holmes Beach

                      Holmes Beach house

                      4 8 3 nights min

                      • 4 bedrooms
                      • sleeps 8
                      • 3 nights min
                      • Swimming pool
                      • Child Friendly
                      • Air conditioning
                      “Family friendly” My family and I enjoyed our stay in Florida and we all loved being able to be under one roof again. My mothers dream was to take us 6 kids, now adults, to the ocean again. Also, she wanted her two new grand-sons to see the ocean fir t
                      …see more

                      Price per night from

                      $344

                      Responds fast!
                      avg. 2 hours 48 minutes

                      Price per night from

                      $344

                      (6) Very Good 

                        17

                        Coconuts Beach Front 106 Ground Floor

                        Anna Maria Island / Holmes Beach

                        Holmes Beach apartment

                        1 4 min stay varies

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

                        Price per night from

                        $229

                        Responds fast!
                        avg. 2 hours 26 minutes

                        Price per night from

                        $229

                          62

                          Gulf-front condo w/ balcony & shared heated pool - steps to the beach & trolley!

                          Anna Maria Island / Holmes Beach

                          Holmes Beach house

                          2 6 7 nights min

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

                          Price per night from

                          $152

                          Responds fast!
                          avg. 1 hour 42 minutes

                          Price per night from

                          $152

                          (31) Excellent 

                          Certificate of Excellence

                            39

                            A Pearl of a Beach Home - with luxury private heated pool and hot tub

                            Anna Maria Island / Holmes Beach

                            Holmes Beach house

                            3 6 7 nights min

                            • 3 bedrooms
                            • sleeps 6
                            • 7 nights min
                            • Beach / lakeside relaxation
                            • Nearest beach 0.4 mi
                            • Swimming pool
                            “out standing place to stay” I would/will stay here again when we come back down. Everything is top notch and the home has everything you need. We enjoyed the pool and hot tube, used it every night. Mike and Lesley are very easy to work with and do
                            …see more

                            Certificate of Excellence

                            Price per night from

                            $270

                            Responds fast!
                            avg. 1 hour 35 minutes

                            Price per night from

                            $270

                              0

                              NEW LISTING! Great condo w/shared pool & access to beach, shopping & dining

                              Anna Maria Island / Holmes Beach

                              Holmes Beach house

                              2 6 28 nights min

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

                              Price per night from

                              $212

                              Responds fast!
                              avg. 1 hour 58 minutes

                              Price per night from

                              $212

                              (7) Excellent 

                              Certificate of Excellence

                                21

                                Absolutely Perfect - Cove at Sandy Pointe #207

                                Anna Maria Island / Holmes Beach

                                Holmes Beach condo

                                2 4 min stay varies

                                • 2 bedrooms
                                • sleeps 4
                                • min stay varies
                                • Beach / lakeside relaxation
                                • Swimming pool
                                • Child Friendly

                                Certificate of Excellence

                                Price per night from

                                $121

                                Price per night from

                                $121

                                (3) Excellent 

                                  23

                                  510 Bayview

                                  Anna Maria Island / Holmes Beach

                                  Holmes Beach house

                                  5 10 min stay varies

                                  • 5 bedrooms
                                  • sleeps 10
                                  • min stay varies
                                  • Swimming pool
                                  • Child Friendly

                                  Price per night from

                                  $818

                                  Price per night from

                                  $818

                                  (36) Excellent 

                                    34

                                    Luxury 3 Bedrooms/3 Full Baths, Private Heated Pool with Waterfall, Beach

                                    Anna Maria Island / Holmes Beach

                                    Holmes Beach house

                                    3 8 7 nights min

                                    • 3 bedrooms
                                    • sleeps 8
                                    • 7 nights min
                                    • Beach / lakeside relaxation
                                    • Nearest beach 0.3 mi
                                    • Swimming pool
                                    “Christmas at the Beach” It was a wonderful family vacation for two families going away for Christmas! There were 4 adults and 6 children! The pool was amazing and the house was perfect! Anna Maria Island is gorgeous and the house is in a perfect locat
                                    …see more

                                    Price per night from

                                    $258

                                    Responds fast!
                                    avg. 1 hour 46 minutes

                                    Price per night from

                                    $258

                                      74

                                      Bright and spacious family home - two blocks from the beach with shared pool

                                      Anna Maria Island / Holmes Beach

                                      Holmes Beach house

                                      3 6 7 nights min

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

                                      Price per night from

                                      $215

                                      Responds fast!
                                      avg. 1 hour 58 minutes

                                      Price per night from

                                      $215

                                      (6) Excellent 

                                        22

                                        Coconuts Poolside Unit 104

                                        Anna Maria Island / Holmes Beach

                                        Holmes Beach apartment

                                        1 4 min stay varies

                                        • 1 bedroom
                                        • sleeps 4
                                        • min stay varies
                                        • Beach / lakeside relaxation
                                        • Swimming pool
                                        • Child Friendly
                                        “The BEST spot on the island!” 24 hours ago we got home from our vacation to Anna Maria at the Coconuts! I'm already wishing we could get a plane and head back!! We absolutely love this island.. And finally lucked out finding the perfect place to stay
                                        …see more

                                        Price per night from

                                        $189

                                        Responds fast!
                                        avg. 2 hours 26 minutes

                                        Price per night from

                                        $189

                                          0

                                          Upscale tropical getaway with private pool, hot tub, elevator, and more!

                                          Anna Maria Island / Holmes Beach

                                          Holmes Beach house

                                          3 6 min stay varies

                                          • 3 bedrooms
                                          • sleeps 6
                                          • min stay varies
                                          • Swimming pool
                                          • Child Friendly
                                          • Car not necessary

                                          Price per night from

                                          $303

                                          Responds fast!
                                          avg. 1 hour 58 minutes

                                          Price per night from

                                          $303

                                          (4) Excellent 

                                          Certificate of Excellence

                                            25

                                            LARGE Key West style POOL HOME Private Tropical Paradise near beach! Anna Maria

                                            Anna Maria Island / Holmes Beach

                                            Holmes Beach house

                                            4 7 min stay varies

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

                                            Certificate of Excellence

                                            Price per night from

                                            $229

                                            Responds fast!
                                            avg. 1 hour 42 minutes

                                            Price per night from

                                            $229

                                              19

                                              Coconuts Beach Front 105 Ground Floor

                                              Anna Maria Island / Holmes Beach

                                              Holmes Beach apartment

                                              1 4 min stay varies

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

                                              Price per night from

                                              $229

                                              Responds fast!
                                              avg. 2 hours 26 minutes

                                              Price per night from

                                              $229

                                              (1) Excellent 

                                                20

                                                Coconuts Beach Front 109 Upstairs

                                                Anna Maria Island / Holmes Beach

                                                Holmes Beach apartment

                                                1 4 7 nights min

                                                • 1 bedroom
                                                • sleeps 4
                                                • 7 nights min
                                                • Beach / lakeside relaxation
                                                • Swimming pool
                                                • Child Friendly

                                                Price per night from

                                                $183

                                                Responds fast!
                                                avg. 2 hours 26 minutes

                                                Price per night from

                                                $183

                                                  0

                                                  Charming cottage-style condo w/ shared pool, Gulf views & easy beach access!

                                                  Anna Maria Island / Holmes Beach

                                                  Holmes Beach house

                                                  1 2 7 nights min

                                                  • 1 bedroom
                                                  • sleeps 2
                                                  • 7 nights min
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Car not necessary

                                                  Price per night from

                                                  $134

                                                  Responds fast!
                                                  avg. 1 hour 58 minutes

                                                  Price per night from

                                                  $134

                                                    23

                                                    3A Villa's on Anna Maria Island

                                                    Anna Maria Island / Holmes Beach

                                                    Holmes Beach villa

                                                    1 4 min stay varies

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

                                                    Price per night from

                                                    $164

                                                    Responds fast!
                                                    avg. 2 hours 26 minutes

                                                    Price per night from

                                                    $164

                                                    (4) Excellent 

                                                      30

                                                      90 steps to the Beach!

                                                      Anna Maria Island / Holmes Beach

                                                      Holmes Beach condo

                                                      2 5 7 nights min

                                                      • 2 bedrooms
                                                      • sleeps 5
                                                      • 7 nights min
                                                      • Beach / lakeside relaxation
                                                      • Swimming pool
                                                      • Child Friendly
                                                      “Amazing” Absolutely loved our stay! Beautiful condo right next to the beach. Had everything we needed! We will definitely be back!
                                                      …see more

                                                      Price per night from

                                                      $201

                                                      Price per night from

                                                      $201

                                                      (5) Very Good 

                                                        23

                                                        Coconuts Two Bedroom 118 Upstairs Courtyard

                                                        Anna Maria Island / Holmes Beach

                                                        Holmes Beach apartment

                                                        2 6 min stay varies

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

                                                        Price per night from

                                                        $229

                                                        Responds fast!
                                                        avg. 2 hours 26 minutes

                                                        Price per night from

                                                        $229

                                                          120

                                                          Oceanview getaway with shared pool & private patio - steps from the beach

                                                          Anna Maria Island / Holmes Beach

                                                          Holmes Beach house

                                                          3 6 min stay varies

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Car not necessary

                                                          Price per night from

                                                          $367

                                                          Responds fast!
                                                          avg. 1 hour 58 minutes

                                                          Price per night from

                                                          $367

                                                            23

                                                            Coconuts Two Bedroom Unit 117 Upstairs Courtyard

                                                            Anna Maria Island / Holmes Beach

                                                            Holmes Beach villa

                                                            1 8 min stay varies

                                                            • 1 bedroom
                                                            • sleeps 8
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Child Friendly
                                                            • Car not necessary

                                                            Price per night from

                                                            $235

                                                            Responds fast!
                                                            avg. 2 hours 26 minutes

                                                            Price per night from

                                                            $235

                                                            (5) Very Good 

                                                              29

                                                              LaPlayita Condo

                                                              Anna Maria Island / Holmes Beach

                                                              Holmes Beach apartment

                                                              2 6 min stay varies

                                                              • 2 bedrooms
                                                              • sleeps 6
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Child Friendly
                                                              “This facility was just what we expected” La Playita is very plain from the outside but the interior was very comfortable. The pool is adequate and the proximity to the beach is convenient. Everything in this condo worked which is often not the case in
                                                              …see more

                                                              Price per night from

                                                              $131

                                                              Price per night from

                                                              $131

                                                              (6) Very Good 

                                                                24

                                                                Coconuts Courtyard 119 Upstairs

                                                                Anna Maria Island / Holmes Beach

                                                                Holmes Beach apartment

                                                                1 4 min stay varies

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

                                                                Price per night from

                                                                $172

                                                                Responds fast!
                                                                avg. 2 hours 26 minutes

                                                                Price per night from

                                                                $172

                                                                  0

                                                                  Charming condo w/ shared pool, Gulf views & great location - walk to the beach!

                                                                  Anna Maria Island / Holmes Beach

                                                                  Holmes Beach house

                                                                  2 4 7 nights min

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

                                                                  Price per night from

                                                                  $152

                                                                  Responds fast!
                                                                  avg. 1 hour 58 minutes

                                                                  Price per night from

                                                                  $152

                                                                    18

                                                                    Coconuts Beach Front 107 Ground Floor

                                                                    Anna Maria Island / Holmes Beach

                                                                    Holmes Beach apartment

                                                                    1 4 min stay varies

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

                                                                    Price per night from

                                                                    $229

                                                                    Responds fast!
                                                                    avg. 2 hours 26 minutes

                                                                    Price per night from

                                                                    $229

                                                                      68

                                                                      Stylish, cozy duplex with shared pool & easy beach access - free WiFi!

                                                                      Anna Maria Island / Holmes Beach

                                                                      Holmes Beach house

                                                                      2 4 7 nights min

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

                                                                      Price per night from

                                                                      $162

                                                                      Responds fast!
                                                                      avg. 1 hour 58 minutes

                                                                      Price per night from

                                                                      $162

                                                                        0

                                                                        Dog-friendly getaway w/ a shared heated pool - walk to the beach!

                                                                        Anna Maria Island / Holmes Beach

                                                                        Holmes Beach house

                                                                        2 6 7 nights min

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

                                                                        Price per night from

                                                                        $169

                                                                        Responds fast!
                                                                        avg. 1 hour 58 minutes

                                                                        Price per night from

                                                                        $169

                                                                        (2) Excellent 

                                                                          22

                                                                          Anna Maria The Pink Flamingo

                                                                          Anna Maria Island / Holmes Beach

                                                                          Holmes Beach cottage

                                                                          2 6 4 nights min

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

                                                                          Price per night from

                                                                          $234

                                                                          Responds fast!
                                                                          avg. 1 hour 36 minutes

                                                                          Price per night from

                                                                          $234

                                                                            52

                                                                            Dog-friendly seaside home w/ private pool & hot tub - great location near beach

                                                                            Anna Maria Island / Holmes Beach

                                                                            Holmes Beach house

                                                                            2 6 7 nights min

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

                                                                            Price per night from

                                                                            $205

                                                                            Responds fast!
                                                                            avg. 1 hour 58 minutes

                                                                            Price per night from

                                                                            $205

                                                                            (1) Excellent 

                                                                              19

                                                                              Coconuts Beach Front 108 Ground floor

                                                                              Anna Maria Island / Holmes Beach

                                                                              Holmes Beach apartment

                                                                              1 4 min stay varies

                                                                              • 1 bedroom
                                                                              • sleeps 4
                                                                              • min stay varies
                                                                              • Beach / lakeside relaxation
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              “Great” Great location! Beautiful view. The condo was was spacious enough for a small group. The beds were a little harder than I would like but the location of the condo and view were great.
                                                                              …see more

                                                                              Price per night from

                                                                              $229

                                                                              Responds fast!
                                                                              avg. 2 hours 26 minutes

                                                                              Price per night from

                                                                              $229