Vacation Rentals with Pool in Madeira Beach

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Filtering by: Swimming pool

1,832 vacation rentals

(7) Excellent 

    24

    Madeira Norte #304 - Across from John's Pass

    Florida / Madeira Beach

    Madeira Beach apartment

    2 5 7 nights min

    • 2 bedrooms
    • sleeps 5
    • 7 nights min
    • Swimming pool
    • Ask about children
    • Air conditioning
    “Great condo!!” We have stayed in this condo before and LOVE IT!! Having 2 full baths with 2 teenagers is definetly a plus when getting ready!! Love sitting out on the balcony over looking Johns Pass and listening to the music at Bamboo Hut!! We will d
    …see more

    Price per night from

    $115

    Price per night from

    $115

    (8) Excellent 

    Certificate of Excellence

      23

      Quaint and charming studio cottage by the beach

      Florida / Madeira Beach

      Madeira Beach cottage

      4 3 nights min

      • sleeps 4
      • 3 nights min
      • Swimming pool
      • Child Friendly
      • Air conditioning
      “Great place” We enjoyed our vacation in this cozy cottage very much. It is well supplied, clean and comfortable. Love the high ceiling and the Murphy bed which gives a more spacious appeal to the small space. Appliances are good. The heated pool is de
      …see more

      Certificate of Excellence

      Price per night from

      $86

      Responds fast!
      avg. 1 hour 16 minutes

      Price per night from

      $86

      (8) Excellent 

        17

        Yacht Club Best!

        Florida / Madeira Beach

        Madeira Beach condo

        2 4 7 nights min

        • 2 bedrooms
        • sleeps 4
        • 7 nights min
        • Beach / lakeside relaxation
        • Nearest beach 0.5 mi
        • Swimming pool
        “get away” My experience was kinda shaky at first , I was given the wrong gate code to get in complex, plus there were a couple of wristbands for pool entry missing and a blind that was messed up,but was able to be fixed in about 15 minutes. Our reserv
        …see more

        Price per night from

        $81

        Price per night from

        $81

        (3) Average 

          24

          BEACH FRONT CONDO *** MADEIRA BEACH

          Florida / Madeira Beach

          Madeira Beach condo

          2 6 7 nights min

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

          Price per night from

          $205

          Price per night from

          $205

            24

            Waterfront Condo w/ Patio & Pool on Madeira Beach!

            Florida / Madeira Beach

            Madeira Beach apartment

            2 6 7 nights min

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

            Price per night from

            $144

            Responds fast!
            avg. 47 minutes

            Price per night from

            $144

              31

              Las Brisas 202-Huge balcony/Amazing views/Sunsets/BBQ/Free Pkg.+WiFi

              Florida / Madeira Beach

              Madeira Beach apartment

              3 8 min stay varies

              • 3 bedrooms
              • sleeps 8
              • min stay varies
              • Swimming pool
              • Ask about children
              • Air conditioning

              Price per night from

              $193

              Price per night from

              $193

                45

                116 - North Madeira

                Florida / Madeira Beach

                Madeira Beach condo

                2 6 7 nights min

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

                Price per night from

                $139

                Responds fast!
                avg. 3 minutes

                Price per night from

                $139

                  27

                  Villa Madeira #502 - Beach Front for up to 6 people!

                  Florida / Madeira Beach

                  Madeira Beach apartment

                  2 6 7 nights min

                  • 2 bedrooms
                  • sleeps 6
                  • 7 nights min
                  • Swimming pool
                  • Ask about children
                  • Air conditioning

                  Price per night from

                  $148

                  Price per night from

                  $148

                    19

                    Late Spring Availability - Affordable - 1 Bedroom overlooking water at MBYC

                    Florida / Madeira Beach

                    Madeira Beach condo

                    1 4 7 nights min

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

                    Price per night from

                    $100

                    Price per night from

                    $100

                      33

                      April is perfect for a beach vaca - 1 BR - Affordable Updated Condo at MBYC!

                      Florida / Madeira Beach

                      Madeira Beach apartment

                      1 4 7 nights min

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

                      Price per night from

                      $92

                      Price per night from

                      $92

                      (1) Excellent 

                        4

                        Charming studio cottage at Gulf Gardens Resort in Madeira Beach

                        Florida / Madeira Beach

                        Madeira Beach cottage

                        1 2 min stay varies

                        • 1 bedroom
                        • sleeps 2
                        • min stay varies
                        • Nearest beach 0.01 mi
                        • Swimming pool
                        • Car not necessary

                        Price per night from

                        $82

                        Price per night from

                        $82

                        (1) Excellent 

                          25

                          Ocean Sands 504 Beachfront Studio Condo

                          Florida / Madeira Beach

                          Madeira Beach apartment

                          1 2 14 nights min

                          • 1 bedroom
                          • sleeps 2
                          • 14 nights min
                          • Swimming pool
                          • Ask about children
                          • Air conditioning

                          Price per night from

                          $89

                          Responds fast!
                          avg. 2 hours 13 minutes

                          Price per night from

                          $89

                          (1) Excellent 

                            25

                            Villa Madeira #301 - Beach Front for up to 6 people!

                            Florida / Madeira Beach

                            Madeira Beach apartment

                            2 6 7 nights min

                            • 2 bedrooms
                            • sleeps 6
                            • 7 nights min
                            • Swimming pool
                            • Ask about children
                            • Air conditioning

                            Price per night from

                            $177

                            Price per night from

                            $177

                            (2) Excellent 

                              28

                              Two Heated Pools! Rare new opening 4/23-4/30!

                              Florida / Madeira Beach

                              Madeira Beach condo

                              2 6 7 nights min

                              • 2 bedrooms
                              • sleeps 6
                              • 7 nights min
                              • Nearest beach 0.5 mi
                              • Swimming pool
                              • Child Friendly

                              Price per night from

                              $115

                              Price per night from

                              $115

                              (9) Excellent 

                                28

                                Beautiful water view condo at the Skyline Resort

                                Florida / Madeira Beach

                                Madeira Beach apartment

                                2 6 min stay varies

                                • 2 bedrooms
                                • sleeps 6
                                • min stay varies
                                • Beach / lakeside relaxation
                                • Swimming pool
                                • Child Friendly
                                “Awesome weekend!” Absolutely love this condo! Perfect location across from the beach, wonderful heated pool: fun for kids and adults. Condo equipped with every need including beach chairs and toys. Kitchen well stocked with dishes, pots, pans. Just ne
                                …see more

                                Price per night from

                                $125

                                Responds fast!
                                avg. 1 hour 11 minutes

                                Price per night from

                                $125

                                (1) Excellent 

                                  26

                                  2BR Madeira Beach Condo Steps from the Beach!

                                  Florida / Madeira Beach

                                  Madeira Beach apartment

                                  2 8 7 nights min

                                  • 2 bedrooms
                                  • sleeps 8
                                  • 7 nights min
                                  • Swimming pool
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $258

                                  Responds fast!
                                  avg. 47 minutes

                                  Price per night from

                                  $258

                                  (54) Excellent 

                                    28

                                    The best guest rated condos at Madeira Beach area!

                                    Florida / Madeira Beach

                                    Madeira Beach apartment

                                    1 4 4 nights min

                                    • 1 bedroom
                                    • sleeps 4
                                    • 4 nights min
                                    • Beach / lakeside relaxation
                                    • Nearest beach 3 mi
                                    • Swimming pool
                                    “Wonderful apartment” Me and my family spent a week in apartment #310 and had a magnificent time. The apartment is fully equipt with everything you possibly could want for your vacation. Nice locaion. Beautiful view from the balcony. The information fr
                                    …see more

                                    Price per night from

                                    $85

                                    Price per night from

                                    $85

                                      24

                                      Direct Beachfront Corner Unit 2 Bed/2 Bath

                                      Florida / Madeira Beach

                                      Madeira Beach condo

                                      2 6 14 nights min

                                      • 2 bedrooms
                                      • sleeps 6
                                      • 14 nights min
                                      • Swimming pool
                                      • Ask about children
                                      • Air conditioning

                                      Price per night from

                                      $155

                                      Price per night from

                                      $155

                                        49

                                        208 - Las Brisas

                                        Florida / Madeira Beach

                                        Madeira Beach apartment

                                        2 6 min stay varies

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

                                        Price per night from

                                        $115

                                        Responds fast!
                                        avg. 3 minutes

                                        Price per night from

                                        $115

                                        (5) Excellent 

                                          20

                                          # 514 Madeira Norte, Madeira Beach

                                          Florida / Madeira Beach

                                          Madeira Beach condo

                                          2 4 7 nights min

                                          • 2 bedrooms
                                          • sleeps 4
                                          • 7 nights min
                                          • Beach / lakeside relaxation
                                          • Nearest beach 0 mi
                                          • Swimming pool
                                          “Perfectly awesome!” Absolutely gorgeous condo. Kitchen and bathroom had everything needed and more. Best location,private type beach, great for families and beautiful. Planning on staying at 514 next year. I personally would install a window treatmen
                                          …see more

                                          Price per night from

                                          $221

                                          Price per night from

                                          $221

                                          (4) Very Good 

                                            45

                                            409 - Madeira Bay Resort

                                            Florida / Madeira Beach

                                            Madeira Beach apartment

                                            2 6 min stay varies

                                            • 2 bedrooms
                                            • sleeps 6
                                            • min stay varies
                                            • Swimming pool
                                            • Child Friendly
                                            • Air conditioning
                                            “409 Madeira Bay Resorts” I Had a great time and would definitely go back!!!! Great views and the unit had everything you could need to cook. Location was excellent!
                                            …see more

                                            Price per night from

                                            $126

                                            Responds fast!
                                            avg. 3 minutes

                                            Price per night from

                                            $126

                                            (3) Excellent 

                                              45

                                              211 - Sandy Shores

                                              Florida / Madeira Beach

                                              Madeira Beach apartment

                                              2 6 min stay varies

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

                                              Price per night from

                                              $127

                                              Responds fast!
                                              avg. 3 minutes

                                              Price per night from

                                              $127

                                              (1) Excellent 

                                                25

                                                Trillium #2C - Beach Front Condo with private balcony!

                                                Florida / Madeira Beach

                                                Madeira Beach apartment

                                                2 6 7 nights min

                                                • 2 bedrooms
                                                • sleeps 6
                                                • 7 nights min
                                                • Swimming pool
                                                • Ask about children
                                                • Air conditioning

                                                Price per night from

                                                $160

                                                Price per night from

                                                $160

                                                  24

                                                  Direct BEACH FRONT! 1/1 Kitchen/Heated Pool/at Johns Pass!

                                                  Florida / Madeira Beach

                                                  Madeira Beach condo

                                                  1 3 min stay varies

                                                  • 1 bedroom
                                                  • sleeps 3
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Air conditioning

                                                  Price per night from

                                                  $126

                                                  Responds fast!
                                                  avg. 2 hours 59 minutes

                                                  Price per night from

                                                  $126

                                                    24

                                                    Posh 1BR Gulf-Front w/ Private Beach & Balcony—Near Shopping & Recreation

                                                    Florida / Madeira Beach

                                                    Madeira Beach condo

                                                    1 4 14 nights min

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

                                                    Price per night from

                                                    $189

                                                    Price per night from

                                                    $189

                                                      83

                                                      Vacation in Paradise... 'Living the Dream'

                                                      Florida / Madeira Beach

                                                      Madeira Beach apartment

                                                      2 6 6 nights min

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

                                                      Price per night from

                                                      $180

                                                      Price per night from

                                                      $180

                                                      (9) Very Good 

                                                        33

                                                        Madeira Norte Unit 416

                                                        Florida / Madeira Beach

                                                        Madeira Beach condo

                                                        2 6 7 nights min

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • 7 nights min
                                                        • Nearest beach 0 mi
                                                        • Swimming pool
                                                        • Child Friendly
                                                        “Wonderful” We had a wonderful time in unit 416. There was everything we needed in the unit and then some!!!!! Don was so accommodating and we felt as if we were in our home. Would definitely go back to Madeira Norte and stay in unit 416.
                                                        …see more

                                                        Price per night from

                                                        $154

                                                        Responds fast!
                                                        avg. 2 hours 34 minutes

                                                        Price per night from

                                                        $154

                                                        (5) Excellent 

                                                          25

                                                          Ocean Sands I Condominium 1208

                                                          Florida / Madeira Beach

                                                          Madeira Beach apartment

                                                          2 4 14 nights min

                                                          • 2 bedrooms
                                                          • sleeps 4
                                                          • 14 nights min
                                                          • Swimming pool
                                                          • Ask about children
                                                          “Great Get Away for 2 Old Stinkers” Our two weeks were spent walking the beaches and lounging at the pool. Yes, it was rough! On our breaks we got dressed and went to different restaurants and relaxed while shopping thru the various boutiques... Yep, t
                                                          …see more

                                                          Price per night from

                                                          $155

                                                          Price per night from

                                                          $155

                                                          (19) Very Good 

                                                            30

                                                            Imagine your dream Florida vacation!

                                                            Florida / Madeira Beach

                                                            Madeira Beach apartment

                                                            2 6 1 night min

                                                            • 2 bedrooms
                                                            • sleeps 6
                                                            • 1 night min
                                                            • Beach / lakeside relaxation
                                                            • Swimming pool
                                                            • Child Friendly
                                                            “Nice getaway” This unit 510 was very nice .my only complaint S was street noise was very loud and the walls super thin could hear everything and everyone's conversations.ceiling fans need cleaning very dusty bathroom shower light out in both bathroo
                                                            …see more

                                                            Price per night from

                                                            $110

                                                            Price per night from

                                                            $110

                                                              26

                                                              Villa Madeira #410 - Beach Front for up to 6 people!

                                                              Florida / Madeira Beach

                                                              Madeira Beach apartment

                                                              2 6 7 nights min

                                                              • 2 bedrooms
                                                              • sleeps 6
                                                              • 7 nights min
                                                              • Swimming pool
                                                              • Ask about children
                                                              • Air conditioning

                                                              Price per night from

                                                              $148

                                                              Price per night from

                                                              $148

                                                              (19) Very Good 

                                                                17

                                                                HAVE IT ALL, WITHOUT BREAKING THE BANK

                                                                Florida / Madeira Beach

                                                                Madeira Beach apartment

                                                                2 6 7 nights min

                                                                • 2 bedrooms
                                                                • sleeps 6
                                                                • 7 nights min
                                                                • Beach / lakeside relaxation
                                                                • Swimming pool
                                                                • Child Friendly
                                                                “A relaxing and memorable vacation” A beautifully decorated condo 3-4 blocks from a great stretch of gulf coast beach. I'd recommend driving over if you want to bring chairs, cooler, etc. Beach parking is inexpensive. The condo itself is quiet, clea
                                                                …see more

                                                                Price per night from

                                                                $116

                                                                Price per night from

                                                                $116

                                                                (3) Excellent 

                                                                  24

                                                                  3 BR Penthouse Condo Located on Boca Ciega Bay

                                                                  Florida / Madeira Beach

                                                                  Madeira Beach condo

                                                                  3 8 7 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 8
                                                                  • 7 nights min
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Air conditioning
                                                                  “Lovely home, Great location!” The condo was very well furnished with everything you could need. We cooked an entire Christmas dinner! My family very much enjoyed our stay here through Christmas and look forward to returning next year. The owner was co
                                                                  …see more

                                                                  Price per night from

                                                                  $172

                                                                  Responds fast!
                                                                  avg. 2 hours 16 minutes

                                                                  Price per night from

                                                                  $172

                                                                  (2) Very Good 

                                                                    12

                                                                    1 Bedroom Madeira Beach Cottage

                                                                    Florida / Madeira Beach

                                                                    Madeira Beach condo

                                                                    1 4 3 nights min

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

                                                                    Price per night from

                                                                    $126

                                                                    Responds fast!
                                                                    avg. 3 hours 49 minutes

                                                                    Price per night from

                                                                    $126

                                                                    (1) Excellent 

                                                                      24

                                                                      Madeira Beach Yacht Club - April Escapes at Incredible Prices!

                                                                      Florida / Madeira Beach

                                                                      Madeira Beach apartment

                                                                      2 6 7 nights min

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

                                                                      Price per night from

                                                                      $104

                                                                      Price per night from

                                                                      $104

                                                                        11

                                                                        Madeira Norte Direct Gulf Front Corner Condo

                                                                        Florida / Madeira Beach

                                                                        Madeira Beach apartment

                                                                        2 6 7 nights min

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

                                                                        Price per night from

                                                                        $298

                                                                        Responds fast!
                                                                        avg. 3 hours 14 minutes

                                                                        Price per night from

                                                                        $298

                                                                          20

                                                                          March cancellation adorable cottage - very affordable! 2 Night Min!

                                                                          Florida / Madeira Beach

                                                                          Madeira Beach studio

                                                                          Studio 3 2 nights min

                                                                          • Studio
                                                                          • sleeps 3
                                                                          • 2 nights min
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $75

                                                                          Price per night from

                                                                          $75

                                                                          (3) Excellent 

                                                                            25

                                                                            Trillium #1C - Beach Front Condo with private balcony!

                                                                            Florida / Madeira Beach

                                                                            Madeira Beach apartment

                                                                            2 6 7 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 6
                                                                            • 7 nights min
                                                                            • Swimming pool
                                                                            • Ask about children
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $160

                                                                            Price per night from

                                                                            $160

                                                                              25

                                                                              The Flamingo Cottage. Walk to Beach, Shops, Dining

                                                                              Florida / Madeira Beach

                                                                              Madeira Beach cottage

                                                                              1 2 7 nights min

                                                                              • 1 bedroom
                                                                              • sleeps 2
                                                                              • 7 nights min
                                                                              • Beach / lakeside relaxation
                                                                              • Swimming pool
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $131

                                                                              Price per night from

                                                                              $131