Vacation Rentals & Beach Rentals in Anna Maria Island

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3,140 beach rentals

(30) Very Good 

    18

    ISLAND TOWNHOUSE - 200 Steps to the BEACH

    Anna Maria Island / Holmes Beach

    Holmes Beach house

    2 4 5 nights min

    • 2 bedrooms
    • sleeps 4
    • 5 nights min
    • Nearest beach 0 mi
    • Child Friendly
    • Air conditioning
    “Even better than you can imagine!” We are so thrilled to have discovered this gem. Barb really has thought of everything you need for a perfect vacation - short or long stay. Quaint boutique shops, excellent dining - one of the best "Lobstah" dinner
    …see more

    Price per night from

    $130

    Responds fast!
    avg. 1 hour 10 minutes

    Price per night from

    $130

    (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

      (38) Excellent 

        123

        Ocean View 3 bedroom, pool, North Shore Drive

        Anna Maria Island / Anna Maria

        Anna Maria house

        3 6 min stay varies

        • 3 bedrooms
        • sleeps 6
        • min stay varies
        • Beach / lakeside relaxation
        • Nearest beach 0 mi
        • Swimming pool
        “Amazing Oceanview Pool Home and Perfect Location On Anna Maria Island” Let me first say that Mark (the home owner) exceeded any and all expectations for our 15th wedding Anniversary! We booked last minute and when we wanted to stay an additional day M
        …see more

        Price per night from

        $237

        Responds fast!
        avg. 49 minutes

        Price per night from

        $237

          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

          $172

          Price per night from

          $172

            48

            Midnightchannel

            Florida / Anna Maria Island

            Anna Maria Island house

            7 16 min stay varies

            • 7 bedrooms
            • sleeps 16
            • min stay varies
            • Swimming pool
            • Child Friendly
            • Air conditioning

            Price per night from

            $573

            Price per night from

            $573

            (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 32 minutes

              Price per night from

              $120

              (28) Very Good 

                17

                Condo In Paradise On Anna Maria Island

                Anna Maria Island / Bradenton Beach

                Bradenton Beach apartment

                2 4 3 nights min

                • 2 bedrooms
                • sleeps 4
                • 3 nights min
                • Beach / lakeside relaxation
                • Child Friendly
                • Car not necessary
                “Perfect island vacation condo” The location is amazing - the beach right across the street and the Bay just 3 blocks on the other side. Shopping and great restaurants were close by. Larry (the owner) is easily accessible and pleasant to deal with. W
                …see more

                Price per night from

                $160

                Responds fast!
                avg. 1 hour 37 minutes

                Price per night from

                $160

                (47) Excellent 

                  44

                  Dolphin Shores Direct Beachfront on Gulf of Mexico

                  Anna Maria Island / Holmes Beach

                  Holmes Beach condo

                  3 4 7 nights min

                  • 3 bedrooms
                  • sleeps 4
                  • 7 nights min
                  • Beach / lakeside relaxation
                  • Child Friendly
                  • Air conditioning
                  “This condo and beach are the the best of the best, great set up,awesome vacation spot!” This was our second year staying here and we absolutely love it! The beach is clean and not crowded at all even on a holiday weekend. The weather is excellent and
                  …see more

                  Price per night from

                  $228

                  Responds fast!
                  avg. 45 minutes

                  Price per night from

                  $228

                    30

                    Two Bed One Bath Beach Side Rental on Anna Maria Island steps to Holmes Beach

                    Anna Maria Island / Holmes Beach

                    Holmes Beach condo

                    1 6 min stay varies

                    • 1 bedroom
                    • sleeps 6
                    • min stay varies
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $92

                    Price per night from

                    $92

                      0

                      Charming cottage w/ free WiFi just two blocks from the beach, near free trolley!

                      Anna Maria Island / Anna Maria

                      Anna Maria house

                      3 8 min stay varies

                      • 3 bedrooms
                      • sleeps 8
                      • min stay varies
                      • Child Friendly
                      • Car not necessary
                      • Air conditioning

                      Price per night from

                      $170

                      Responds fast!
                      avg. 2 hours 30 minutes

                      Price per night from

                      $170

                        185

                        Bright and cheery waterfront home with private pool and spa

                        Anna Maria Island / Anna Maria

                        Anna Maria house

                        3 6 min stay varies

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

                        Price per night from

                        $323

                        Responds fast!
                        avg. 2 hours 30 minutes

                        Price per night from

                        $323

                          21

                          Canalfront home w/ pool, dock & lanai - 2 blocks to the beach, dogs OK!

                          Anna Maria Island / Anna Maria

                          Anna Maria house

                          3 6 min stay varies

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

                          Price per night from

                          $241

                          Responds fast!
                          avg. 2 hours 30 minutes

                          Price per night from

                          $241

                          (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

                            $186

                            Responds fast!
                            avg. 2 hours 32 minutes

                            Price per night from

                            $186

                            (10) Excellent 

                              53

                              2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!

                              Anna Maria Island / Bradenton Beach

                              Bradenton Beach cottage

                              3 8 7 nights min

                              • 3 bedrooms
                              • sleeps 8
                              • 7 nights min
                              • Beach / lakeside relaxation
                              • Child Friendly
                              • Car not necessary
                              “Perfect Beach House” We loved the quaint little duplex. The house was clean and ready for us when we arrived. Tim was a dream to work with. The A/C one of the units went out while we were there, and he had someone there first thing to take care of i
                              …see more

                              Price per night from

                              $119

                              Price per night from

                              $119

                              (2) Very Good 

                                19

                                BAY FRONT HOUSE WITH PRIVATE DOCK

                                Anna Maria Island / Bradenton Beach

                                Bradenton Beach house

                                2 6 2 nights min

                                • 2 bedrooms
                                • sleeps 6
                                • 2 nights min
                                • Nearest beach 0.1 mi
                                • Car not necessary
                                • Air conditioning

                                Price per night from

                                $201

                                Price per night from

                                $201

                                  0

                                  NEW LISTING! Breezy condo w/shared pool -minutes from beach & dining

                                  Anna Maria Island / Bradenton Beach

                                  Bradenton Beach house

                                  1 4 min stay varies

                                  • 1 bedroom
                                  • sleeps 4
                                  • min stay varies
                                  • Swimming pool
                                  • Child Friendly
                                  • Car not necessary

                                  Price per night from

                                  $92

                                  Responds fast!
                                  avg. 2 hours 30 minutes

                                  Price per night from

                                  $92

                                  (1) Excellent 

                                    14

                                    AMI Bradenton Beach Ground Condo

                                    Anna Maria Island / Bradenton Beach

                                    Bradenton Beach condo

                                    2 4 7 nights min

                                    • 2 bedrooms
                                    • sleeps 4
                                    • 7 nights min
                                    • Beach / lakeside relaxation
                                    • Swimming pool
                                    • Air conditioning

                                    Price per night from

                                    $172

                                    Price per night from

                                    $172

                                    (3) Excellent 

                                      28

                                      250 Feet from the Beach

                                      Anna Maria Island / Bradenton Beach

                                      Bradenton Beach townhouse

                                      2 6 4 nights min

                                      • 2 bedrooms
                                      • sleeps 6
                                      • 4 nights min
                                      • Child Friendly
                                      • Car not necessary
                                      • Air conditioning

                                      Price per night from

                                      $171

                                      Responds fast!
                                      avg. 1 hour 33 minutes

                                      Price per night from

                                      $171

                                        31

                                        742 Jacaranda Rd

                                        Anna Maria Island / Anna Maria

                                        Anna Maria house

                                        3 6 min stay varies

                                        • 3 bedrooms
                                        • sleeps 6
                                        • min stay varies
                                        • Child Friendly

                                        Price per night from

                                        $213

                                        Price per night from

                                        $213

                                          43

                                          Beautiful, well-maintained home w/private pool - walk to beach, dining, & more!

                                          Anna Maria Island / Anna Maria

                                          Anna Maria 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. 2 hours 30 minutes

                                          Price per night from

                                          $303

                                            0

                                            Oceanfront dog-friendly home w/private pool & ocean view - right on the beach!

                                            Anna Maria Island / Anna Maria

                                            Anna Maria house

                                            3 6 min stay varies

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

                                            Price per night from

                                            $535

                                            Responds fast!
                                            avg. 2 hours 30 minutes

                                            Price per night from

                                            $535

                                              0

                                              Spacious house w/ private yard & great location near the beach - dogs ok!

                                              Anna Maria Island / Anna Maria

                                              Anna Maria house

                                              2 6 min stay varies

                                              • 2 bedrooms
                                              • sleeps 6
                                              • min stay varies
                                              • Child Friendly
                                              • Car not necessary
                                              • Air conditioning

                                              Price per night from

                                              $170

                                              Responds fast!
                                              avg. 2 hours 30 minutes

                                              Price per night from

                                              $170

                                              (23) Very Good 

                                                17

                                                Ohana Hale North 2 Bedroom on Anna Maria

                                                Anna Maria Island / Holmes Beach

                                                Holmes Beach house

                                                2 6 min stay varies

                                                • 2 bedrooms
                                                • sleeps 6
                                                • min stay varies
                                                • Beach / lakeside relaxation
                                                • Child Friendly
                                                • Car not necessary
                                                “Home is very comfortable and we really enjoyed our stay” Home is very comfortable. Loved the kitchen and owners could not be more accomadating.
                                                …see more

                                                Price per night from

                                                $155

                                                Responds fast!
                                                avg. 3 hours 59 minutes

                                                Price per night from

                                                $155

                                                  28

                                                  Bermuda Bay 1467

                                                  Anna Maria Island / Bradenton Beach

                                                  Bradenton Beach condo

                                                  3 6 min stay varies

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

                                                  Price per night from

                                                  $172

                                                  Responds fast!
                                                  avg. 2 hours 30 minutes

                                                  Price per night from

                                                  $172

                                                  (12) Excellent 

                                                  Certificate of Excellence

                                                    27

                                                    Watch Sunsets, Dolphins, or Just Relax - Bermuda Bay 1453

                                                    Anna Maria Island / Bradenton Beach

                                                    Bradenton Beach apartment

                                                    3 7 7 nights min

                                                    • 3 bedrooms
                                                    • sleeps 7
                                                    • 7 nights min
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 0 mi
                                                    • Swimming pool
                                                    “Great place, great location, and everything you need!” We stayed here to go to my sister's wedding at The Beach House. We loved this townhouse. It had spacious rooms, beautiful decor, and a great view of the ocean from the balcony. I was really imp
                                                    …see more

                                                    Certificate of Excellence

                                                    Price per night from

                                                    $196

                                                    Price per night from

                                                    $196

                                                      81

                                                      Dog-friendly cottage w/ private heated pool - minutes from beaches & more!

                                                      Anna Maria Island / Anna Maria

                                                      Anna Maria house

                                                      4 8 min stay varies

                                                      • 4 bedrooms
                                                      • sleeps 8
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Child Friendly
                                                      • Car not necessary

                                                      Price per night from

                                                      $356

                                                      Responds fast!
                                                      avg. 2 hours 30 minutes

                                                      Price per night from

                                                      $356

                                                      (1) Excellent 

                                                        14

                                                        Coconuts Tahitian 205

                                                        Anna Maria Island / Holmes Beach

                                                        Holmes Beach apartment

                                                        1 4 min stay varies

                                                        • 1 bedroom
                                                        • sleeps 4
                                                        • min stay varies
                                                        • Child Friendly
                                                        • Air conditioning
                                                        “60th birthday” This rental was exactly what we were told and was a perfect location. Slept three perfectly. Beds were very comfy and anything you needed was available. Thinking of renting for month next year!
                                                        …see more

                                                        Price per night from

                                                        $148

                                                        Responds fast!
                                                        avg. 2 hours 26 minutes

                                                        Price per night from

                                                        $148

                                                          0

                                                          Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK!

                                                          Anna Maria Island / Anna Maria

                                                          Anna Maria house

                                                          2 6 min stay varies

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

                                                          Price per night from

                                                          $187

                                                          Responds fast!
                                                          avg. 2 hours 30 minutes

                                                          Price per night from

                                                          $187

                                                          (1) Excellent 

                                                            56

                                                            Cute cottage with patio and amazing location near Pine St. and the beach

                                                            Anna Maria Island / Anna Maria

                                                            Anna Maria house

                                                            2 6 3 nights min

                                                            • 2 bedrooms
                                                            • sleeps 6
                                                            • 3 nights min
                                                            • Child Friendly
                                                            • Car not necessary
                                                            • Air conditioning

                                                            Price per night from

                                                            $212

                                                            Responds fast!
                                                            avg. 2 hours 30 minutes

                                                            Price per night from

                                                            $212

                                                            (4) Excellent 

                                                              22

                                                              BEACHFRONT HOME, PRIVATE BEACH, DOGS STAY FREE, GREAT VIEWS, WALKING BEACH

                                                              Anna Maria Island / Anna Maria

                                                              Anna Maria house

                                                              3 8 min stay varies

                                                              • 3 bedrooms
                                                              • sleeps 8
                                                              • min stay varies
                                                              • Child Friendly
                                                              • Car not necessary
                                                              • Air conditioning

                                                              Price per night from

                                                              $227

                                                              Responds fast!
                                                              avg. 1 hour 47 minutes

                                                              Price per night from

                                                              $227

                                                              (2) Very Good 

                                                                15

                                                                AMI Island Living -Walk to Beach-Ground Level Unit

                                                                Anna Maria Island / Bradenton Beach

                                                                Bradenton Beach apartment

                                                                2 4 7 nights min

                                                                • 2 bedrooms
                                                                • sleeps 4
                                                                • 7 nights min
                                                                • Beach / lakeside relaxation
                                                                • Swimming pool
                                                                • Suitable for children age 5+

                                                                Price per night from

                                                                $172

                                                                Price per night from

                                                                $172

                                                                  33

                                                                  'Seascape' PEACEFUL, Newly renovated, steps to beach & fishing dock on bay

                                                                  Anna Maria Island / Bradenton Beach

                                                                  Bradenton Beach condo

                                                                  1 2 3 nights min

                                                                  • 1 bedroom
                                                                  • sleeps 2
                                                                  • 3 nights min
                                                                  • Nearest beach 0 mi
                                                                  • Child Friendly
                                                                  • Car not necessary

                                                                  Price per night from

                                                                  $205

                                                                  Responds fast!
                                                                  avg. 3 hours 44 minutes

                                                                  Price per night from

                                                                  $205

                                                                  (1) Very Good 

                                                                    58

                                                                    Waterfront and dog-friendly home with private pool, dock, views, and lanai!

                                                                    Anna Maria Island / Anna Maria

                                                                    Anna Maria house

                                                                    3 8 min stay varies

                                                                    • 3 bedrooms
                                                                    • sleeps 8
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Child Friendly
                                                                    • Car not necessary

                                                                    Price per night from

                                                                    $281

                                                                    Responds fast!
                                                                    avg. 2 hours 30 minutes

                                                                    Price per night from

                                                                    $281

                                                                    (22) Very Good 

                                                                      42

                                                                      Steps to Beach, Gulf View, Footprints in the Sand

                                                                      Anna Maria Island / Bradenton Beach

                                                                      Bradenton Beach apartment

                                                                      2 4 7 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 4
                                                                      • 7 nights min
                                                                      • Beach / lakeside relaxation
                                                                      • Nearest beach 0 mi
                                                                      • Child Friendly
                                                                      “Footprints in the sand” We had a great time on Anna Maria Island. Footprints in the sand,its closeness to the beaches,restaurants and shops made it very convenient.The place was well stocked with all basic needs & amenities that were listed. Thanks
                                                                      …see more

                                                                      Price per night from

                                                                      $146

                                                                      Responds fast!
                                                                      avg. 2 hours 9 minutes

                                                                      Price per night from

                                                                      $146

                                                                      (2) Excellent 

                                                                        26

                                                                        CHARMING 2 Bed 2 Bath with Heated PRIVATE HEATED Pool SPA Sleeps 6 F

                                                                        Anna Maria Island / Holmes Beach

                                                                        Holmes Beach townhouse

                                                                        2 6 min stay varies

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

                                                                        Price per night from

                                                                        $228

                                                                        Price per night from

                                                                        $228

                                                                        (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

                                                                          $144

                                                                          Price per night from

                                                                          $144

                                                                          (1) Excellent 

                                                                            74

                                                                            Charming house with private heated pool, patio, and grill - steps from beach

                                                                            Anna Maria Island / Anna Maria

                                                                            Anna Maria house

                                                                            3 6 min stay varies

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

                                                                            Price per night from

                                                                            $241

                                                                            Responds fast!
                                                                            avg. 2 hours 30 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

                                                                              About Anna Maria Island

                                                                              Just south of Tampa Bay on the turquoise Gulf of Mexico, sits a quaint Barrier Island located on Florida's West Coast. Lined by a seven-mile strip of beautiful white-sand beaches, Anna Maria Island is a cozy paradise that has long been considered one of the state's hidden gems. Here, "Old Florida" charm abounds and visitors can get a feel for Florida, the way it used to be.

                                                                              With seven miles of uninterrupted beach, Anna Maria Island offers plenty of opportunities to enjoy fun in the sun and explore. The island shares its beach life with local wildlife. Turtles visit from May - November every year (nest tours are offered in the summer) and year round visitors shouldn't be surprised to see manatees, dolphins, rays and exotic fish beyond the waves.

                                                                              In addition to its picturesque beaches, Anna Maria Island is home to many award-winning dining options, including bistros, cafes and restaurants (there are no chain restaurants to be found). The island has been recognized nationally for its locally sourced food, unique menu items and on-the-water locations offering top views. Diners can expect gourmet dining options offering cuisine from England, France, Germany, Italy, Asia and Spain, as well as "Floribbean" dishes and seafood delicacies straight from the nearby sea. Top seafood choices include: grouper, red snapper, mullet and blue crab. Visitors are even invited to bring their catch into some of the area's top restaurants, like the Sandbar and Beachhouse.

                                                                              For guests looking for fun off the sand as well, there are many art galleries, museums or aquariums in the area. And, the island is surrounded by nature parks and gorgeous naturally landscaped paths worth exploring.

                                                                              Anna Maria Island also offers many top options for shopping at its many souvenir, jewelry, clothing and antique stores. Pine Avenue (known as the Greenest Little Main Street in America) is lined by great stylish boutiques and specialty shops and leads directly on to the 100 year old Anna Maria City Pier which offers picturesque views of the bay. Holmes Beach offers seven blocks of stores, small unique gift shops, adorable café's, art galleries and a grocery store. Additionally, stores on the newly restored Bridge Street in Bradenton Beach offers an unusual blend of arts and crafts unique to the island, reflecting its Bohemian roots.

                                                                              Anna Maria Island also boasts a wide variety of accommodations ranging from historic bed and breakfasts, to beach-side cottages, cozy luxury homes, as well as condo rentals and spacious villas, which are all locally owned and operated and offer a unique experience. Tall sky-rise and commercial buildings do not exist on Anna Maria Island, with most accommodations measuring at less than three stories.

                                                                              Additionally, the island is becoming a top choice for beach destination weddings. So much so that many are referring to the setting as the "Beach Wedding Capital of Florida". Forbes named Anna Maria Island the "#3 Prettiest City in the Country" in 2013 and was a "TripAdvisor Traveler's Choice Destination Winner 2013 and 2014" and #3 of the top 10 islands in the US to go to in 2014.

                                                                              Information provided by: Bradenton Area Convention and Visitor's Bureau