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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!

  • 74 properties returned
  • Sort by: Random
  • Flip Flop Oasis

    Multi-Family
    • 6
    • 6
    • Pool
    • No Pets
    • Sleeps 12
    • 7 Views
  • 3

    Blue Lagoon 5

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

    Buena Vista 4

    Condominium
    • 4
    • 3 Full Baths , 1 Half Baths
    • Pool
    • No Pets
    • Sleeps 8
    • 80 Views
  • 2

    Palm Isle Village 3201 - TipSea Turtle

    Condominium
    • 2
    • 2
    • Pool
    • No Pets
    • Sleeps 6
    • 26 Views
  • 7

    Aquarius

    Home
    • 4
    • 3
    • Pool
    • Dogs Allowed
    • Sleeps 8
    • 45 Views
  • 5

    Coquina Sands

    Multi-Family
    • 3
    • 3 Full Baths , 1 Half Baths
    • Pool
    • Dogs Allowed
    • Sleeps 6
    • 24 Views
  • 2

    The Villas 3B

    Condominium
    • 2
    • 1
    • No Pets
    • Sleeps 6
    • 40 Views
  • Island Jewel

    Home
    • 3
    • 2 Full Baths , 1 Half Baths
    • Pool
    • No Pets
    • Sleeps 6
    • 54 Views
  • 29

    Coral Castle

    Home
    • 5
    • 3 Full Baths , 1 Half Baths
    • Pool
    • Dogs Allowed
    • Sleeps 10
    • 70 Views
  • Seashells and Sunsets

    Home
    • 5
    • 6
    • Pool
    • No Pets
    • Sleeps 10
    • 15 Views
  • 1

    Martinique404N

    Condominium
    • 2
    • 2
    • Pool
    • Dogs Allowed
    • Sleeps 6
    • 38 Views
  • 4

    La Casa Marie

    Condominium
    • 3
    • 2 Full Baths , 1 Half Baths
    • Pool
    • No Pets
    • Sleeps 6
    • 16 Views