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Holmes Beach Vacation Rentals

Holmes Beach is a small beach town on Anna Maria Island with that charming Old Florida Town feel that vacationers crave. Holmes Beach is a year-round vacation destination with some of the best sunsets anywhere in the country. There’s miles of soft, white, sandy beaches to explore and gorgeous emerald green water to swim in. With around 5,000 residents, Holmes Beach is the largest of the three communities that make up Anna Maria Island.

You’ll find the perfect Holmes Beach vacation rental at Island Real. Whether you’re looking for a luxury rental with private pool access, a rental with its own canal access, or a beachfront house rental big enough for the whole family - we have you covered! If you’re traveling with a canine companion, be sure to check out our pet friendly rentals.

Check out our favorite things to do in Holmes Beach, read our “Top 10” guides, and more on our blog!

  • 78 properties returned
  • Sort by: Random
  • Coconuts 108

    Condominium
    • 1
    • 1
    • Pool
    • No Pets
    • Sleeps 4
    • 20 Views
  • 5

    Gulf Place #23

    Condominium
    • 2
    • 2
    • Pool
    • No Pets
    • Sleeps 6
    • 31 Views
  • 12

    My Big Fat Beach House

    Home
    • 5
    • 3
    • Pool
    • No Pets
    • Sleeps 10
    • 50 Views
  • 3

    Casa Sierra 205A

    Condominium
    • 2
    • 2
    • Pool
    • Dogs Allowed
    • Sleeps 6
    • 16 Views
  • 7

    Fernweh

    Home
    • 4
    • 4
    • Pool
    • No Pets
    • Sleeps 8
    • 42 Views
  • 1

    Coconuts 101

    Condominium
    • 1
    • 1
    • Pool
    • No Pets
    • Sleeps 4
    • 32 Views
  • 1

    DreAMI

    Home
    • 3
    • 3 Full Baths , 1 Half Baths
    • Pool
    • Dogs Allowed
    • Sleeps 6
    • 18 Views
  • 2

    Palm Isle Village 3203 - Pink Flamingo

    Condominium
    • 2
    • 2
    • Pool
    • No Pets
    • Sleeps 6
    • 12 Views
  • 1

    Harrington Bungalow 6

    Home
    • 3
    • 2
    • Pool
    • No Pets
    • Sleeps 6
    • 25 Views
  • EverLasting SunSets A

    Multi-Family
    • 1
    • 1
    • Pool
    • No Pets
    • Sleeps 3
    • 23 Views
  • 9

    Appletini

    Multi-Family
    • 2
    • 2
    • Pool
    • Dogs Allowed
    • Sleeps 6
    • 42 Views
  • 8

    Sea Glass

    Multi-Family
    • 3
    • 2
    • Pool
    • No Pets
    • Sleeps 6
    • 113 Views