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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!

  • 76 properties returned
  • Sort by: Random
  • North Beach Village 40 - Sans Souci

    Condominium
    • 3
    • 2 Full Baths , 1 Half Baths
    • Pool
    • No Pets
    • Sleeps 6
    • 17 Views
  • 5

    Casa Morado

    Home
    • 4
    • 3 Full Baths , 1 Half Baths
    • Pool
    • Dogs Allowed
    • Sleeps 8
    • 37 Views
  • 1

    Palm Isle Village 3210

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

    The Villas 3A

    Condominium
    • 1
    • 1
    • Pool
    • No Pets
    • Sleeps 4
    • 19 Views
  • 3

    Flirty Flamingo

    Home
    • 2
    • 2
    • No Pets
    • Sleeps 4
    • 30 Views
  • Coquina Sands

    Multi-Family
    • 3
    • 3 Full Baths , 1 Half Baths
    • Pool
    • Dogs Allowed
    • Sleeps 6
    • 17 Views
  • 8

    North Beach Village 6301

    Condominium
    • 3
    • 2
    • Pool
    • No Pets
    • Sleeps 6
    • 44 Views
  • 7

    Aquarius

    Home
    • 4
    • 3
    • Pool
    • Dogs Allowed
    • Sleeps 8
    • 44 Views
  • Waters Edge 209S

    Condominium
    • 2
    • 2
    • Pool
    • No Pets
    • Sleeps 4
    • 25 Views
  • 10

    Palm Isle Village 3211

    Condominium
    • 1
    • 1 Full Baths , 1 Half Baths
    • Pool
    • Dogs Allowed
    • Sleeps 4
    • 16 Views
  • Hidden Haven

    Home
    • 4
    • 2
    • Pool
    • No Pets
    • Sleeps 8
    • 29 Views
  • The Haven

    Home
    • 3
    • 2 Full Baths , 1 Half Baths
    • Pool
    • Dogs Allowed
    • Sleeps 8
    • 21 Views