Vacation Rentals & Apartments in Holmes Beach

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

3,330 apartments

(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

    (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

        (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

            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

              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

              (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

                (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

                  (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

                    (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

                      (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

                        $149

                        Responds fast!
                        avg. 1 hour 32 minutes

                        Price per night from

                        $149

                        (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. 1 hour 32 minutes

                          Price per night from

                          $229

                          (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

                              22

                              Gulf Sound - A

                              Anna Maria Island / Holmes Beach

                              Holmes Beach condo

                              2 6 min stay varies

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

                              Price per night from

                              $163

                              Responds fast!
                              avg. 2 hours 30 minutes

                              Price per night from

                              $163

                                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 37 minutes

                                Price per night from

                                $170

                                  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

                                  $315

                                  Responds fast!
                                  avg. 1 hour 27 minutes

                                  Price per night from

                                  $315

                                    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 37 minutes

                                    Price per night from

                                    $241

                                    (1) Excellent 

                                      34

                                      private pool/spa beach gear

                                      Anna Maria Island / Holmes Beach

                                      Holmes Beach townhouse

                                      4 8 min stay varies

                                      • 4 bedrooms
                                      • sleeps 8
                                      • min stay varies
                                      • Child Friendly
                                      • Air conditioning

                                      Price per night from

                                      $434

                                      Price per night from

                                      $434

                                      (5) Excellent 

                                        15

                                        Fully Remodeled Vacation Rental Anna Maria Island

                                        Anna Maria Island / Holmes Beach

                                        Holmes Beach apartment

                                        2 6 min stay varies

                                        • 2 bedrooms
                                        • sleeps 6
                                        • min stay varies
                                        • Beach / lakeside relaxation
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $126

                                        Responds fast!
                                        avg. 2 hours 31 minutes

                                        Price per night from

                                        $126

                                          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 37 minutes

                                          Price per night from

                                          $215

                                          (4) Very Good 

                                            14

                                            Anna Maria Island (blue) Cast Away Rental

                                            Anna Maria Island / Holmes Beach

                                            Holmes Beach apartment

                                            2 6 3 nights min

                                            • 2 bedrooms
                                            • sleeps 6
                                            • 3 nights min
                                            • Beach / lakeside relaxation
                                            • Child Friendly
                                            • Car not necessary

                                            Price per night from

                                            $212

                                            Price per night from

                                            $212

                                            (5) Very Good 

                                              14

                                              Spectacular Beach House With GulfView Only Steps to a Pristine Beach

                                              Anna Maria Island / Holmes Beach

                                              Holmes Beach house

                                              3 6 7 nights min

                                              • 3 bedrooms
                                              • sleeps 6
                                              • 7 nights min
                                              • Child Friendly
                                              • Air conditioning
                                              • Private garden

                                              Price per night from

                                              $344

                                              Price per night from

                                              $344

                                                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 27 minutes

                                                Price per night from

                                                $152

                                                (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

                                                  (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

                                                      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. 29 minutes

                                                      Price per night from

                                                      $296

                                                      (6) Excellent 

                                                        13

                                                        On the Beach Paradise d

                                                        Anna Maria Island / Holmes Beach

                                                        Holmes Beach cottage

                                                        2 6 4 nights min

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • 4 nights min
                                                        • Beach / lakeside relaxation
                                                        • Child Friendly
                                                        • Air conditioning
                                                        “Absolutely beautiful!” Everything was perfect. Enjoyed coffee on the beach every morning and beautiful sunsets every evening. Can't wait to go back next year!
                                                        …see more

                                                        Price per night from

                                                        $207

                                                        Responds fast!
                                                        avg. 1 hour 54 minutes

                                                        Price per night from

                                                        $207

                                                        (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

                                                          $252

                                                          Responds fast!
                                                          avg. 1 hour 46 minutes

                                                          Price per night from

                                                          $252

                                                          (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

                                                            (5) Excellent 

                                                              27

                                                              Island Love Nest

                                                              Anna Maria Island / Holmes Beach

                                                              Holmes Beach apartment

                                                              2 6 5 nights min

                                                              • 2 bedrooms
                                                              • sleeps 6
                                                              • 5 nights min
                                                              • Beach / lakeside relaxation
                                                              • Nearest beach 0.3 mi
                                                              • Child Friendly
                                                              “Relaxing refuge” We had such a relaxing time during our stay. The condo is very clean and comfy with lots of little touches to make your stay even better. Its cozy enough for a couple but also has room for thr whole family. We enjoyed reading by the
                                                              …see more

                                                              Price per night from

                                                              $229

                                                              Price per night from

                                                              $229

                                                              (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

                                                                (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

                                                                  $179

                                                                  Responds fast!
                                                                  avg. 1 hour 32 minutes

                                                                  Price per night from

                                                                  $179

                                                                    48

                                                                    Light-filled home w/ screened balcony - one block to the beach, small dogs OK!

                                                                    Anna Maria Island / Holmes Beach

                                                                    Holmes Beach house

                                                                    2 6 7 nights min

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

                                                                    Price per night from

                                                                    $152

                                                                    Responds fast!
                                                                    avg. 1 hour 27 minutes

                                                                    Price per night from

                                                                    $152

                                                                      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 37 minutes

                                                                      Price per night from

                                                                      $212

                                                                        29

                                                                        Holmes Beach on Anna Maria Island Vacation Rental Cottage Steps to the Beach

                                                                        Anna Maria Island / Holmes Beach

                                                                        Holmes Beach condo

                                                                        2 5 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 5
                                                                        • min stay varies
                                                                        • Child Friendly
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $109

                                                                        Price per night from

                                                                        $109

                                                                          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 37 minutes

                                                                          Price per night from

                                                                          $134

                                                                          (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

                                                                            (4) Excellent 

                                                                              15

                                                                              Shady Palms - Real Beachfront on the Gulf of Mexico

                                                                              Anna Maria Island / Holmes Beach

                                                                              Holmes Beach house

                                                                              2 6 7 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 6
                                                                              • 7 nights min
                                                                              • Beach / lakeside relaxation
                                                                              • Child Friendly
                                                                              • Air conditioning
                                                                              “Old Florida Charm” This home had all the beauty and grace of Old Florida! It was well furnished with amenities plus delightful treasures of decor.The view of the Gulf was outstanding from many windows throughout the house as well as from the shady ba
                                                                              …see more

                                                                              Price per night from

                                                                              $425

                                                                              Price per night from

                                                                              $425

                                                                              About Holmes Beach

                                                                              Holmes Beach is a stretch of pristine white sand along the shoreline of Anna Maria Island, a tropical paradise just off south Florida's Gulf Coast. The beach and the entire island make a postcard perfect summer vacation destination. Despite Anna Maria's tropical beauty, inviting local culture and fascinating natural biodiversity, the island has remained protected from over development and feels warm, friendly and secluded even during the height of the summer.

                                                                              Come here for the best of a southern Florida family vacation or romantic island getaway. Explore the museums and cultural venues, experience world class restaurants and nightspots with a relaxed, laid back atmosphere, and soak in the golden sun of Anna Maria's gorgeous beaches. There's no better way to escape from the bustle of everyday life and make some fun and lasting memories.

                                                                              Here are a few additional suggestions as you plan your trip:

                                                                              • Explore the island by bicycle: Anna Maria is a perfect place to explore by foot, but a bicycle offers a fun way to get around and see the sights. Rent a bike for an afternoon or a weekend and explore the markets, the beach and the trails.
                                                                              • Take an eco-tour: Rent a kayak and take a guided excursion or schedule a charter boat tour to learn more about the dazzling biodiversity of Florida's ocean ecosystems, coastlines and salt marshes.
                                                                              • Play on the beach: surf, swim, scuba dive, or go parasailing and see the coastline from above. Or just bring a book, stake out a place in the soft sand, and relax.
                                                                              • See a show: Enjoy a live theater performance courtesy of the Island Players or Manatee Players, or book tickets to a music or dance performance at the Asolo Center for the Performing Arts.
                                                                              • Hike the trails: Go hiking, exploring and bird watching along the trails of DeSoto National Park.
                                                                              • Visit the museums: Start with the Ringling Museum of art and the G-Wiz Science Museum for fascinating hands-on exhibits. Most of the museums and cultural venues around Holmes beach are perfect for adults and children of any age.

                                                                              You'll never run out of things to do on Anna Maria Island. Play a round golf, enjoy an afternoon of luxury in an elegant spa, or splash the day away at any of several local water parks. Just be sure to find a sleek summer condo or elegant vacation house with beautiful views of the ocean so that when you're ready to end the day you can return to the perfect vacation rental that offers everything you and your family need.