Holiday travel on Anna Maria Island
Holiday and Long-Weekend Guides
Plan your holiday escape in Holmes Beach with guides that match your dates. Each page points you to open dates and a relaxed rhythm for beach days, pool resets, and easy island dining.
Holiday travel
New Year's Day Stays in Holmes Beach (Anna Maria Island)
Plan a New Year's Day escape in Holmes Beach with beach walks, a private heated pool, and easy access to Anna Maria Island dining.
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Long weekends
New Year's Eve Stays in Holmes Beach (Anna Maria Island)
Celebrate New Year's Eve on Anna Maria Island with a boutique Holmes Beach stay, a private pool, and easy beach access.
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Family breaks
New Year's Week Stays in Holmes Beach (Anna Maria Island)
Plan a New Year's Week stay in Holmes Beach with a private heated pool, walk-to-beach access, and a relaxed island rhythm.
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Couples escapes
New Year's Weekend Stays in Holmes Beach (Anna Maria Island)
Book a New Year's Weekend trip to Anna Maria Island for beach walks, a private pool, and relaxed Holmes Beach dining.
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Holiday travel
MLK Weekend Stays in Holmes Beach (Anna Maria Island)
Plan an MLK Weekend escape in Holmes Beach with walk-to-beach access, a private heated pool, and easy island dining.
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Long weekends
Presidents' Day Weekend Stays in Holmes Beach (Anna Maria Island)
Escape for Presidents' Day Weekend in Holmes Beach with a private pool, walk-to-beach access, and a calm island pace.
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Family breaks
Presidents' Week Stays in Holmes Beach (Anna Maria Island)
Plan a Presidents' Week stay on Anna Maria Island for beach time, a private heated pool, and easy family routines.
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Couples escapes
Valentine's Weekend Stays in Holmes Beach (Anna Maria Island)
Plan a Valentine's Weekend escape in Holmes Beach with a private heated pool, walkable dining, and quiet beach sunsets.
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Holiday travel
Spring Break Stays in Holmes Beach (Anna Maria Island)
Book a Spring Break stay on Anna Maria Island with walk-to-beach access, a private heated pool, and a relaxed Holmes Beach base.
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Long weekends
Spring Break Week Stays in Holmes Beach (Anna Maria Island)
Plan a full Spring Break week in Holmes Beach with a private pool, walkable dining, and easy beach access.
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Family breaks
Easter Weekend Stays in Holmes Beach (Anna Maria Island)
Celebrate Easter Weekend on Anna Maria Island with beach walks, a private heated pool, and a peaceful Holmes Beach base.
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Couples escapes
Easter Week Stays in Holmes Beach (Anna Maria Island)
Plan an Easter Week stay in Holmes Beach with a private heated pool, walk-to-beach access, and an easy island rhythm.
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Holiday travel
Mother's Day Weekend Stays in Holmes Beach (Anna Maria Island)
Treat mom to a Mother's Day Weekend in Holmes Beach with a private heated pool, beach walks, and easy dining options.
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Long weekends
Memorial Day Weekend Stays in Holmes Beach (Anna Maria Island)
Kick off summer with Memorial Day Weekend in Holmes Beach, featuring walk-to-beach access, a private pool, and a relaxed island vibe.
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Family breaks
Memorial Day Week Stays in Holmes Beach (Anna Maria Island)
Plan a Memorial Day Week stay in Holmes Beach with a heated pool, walk-to-beach access, and a calm island routine.
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Couples escapes
Father's Day Weekend Stays in Holmes Beach (Anna Maria Island)
Plan a Father's Day Weekend escape to Holmes Beach with a private heated pool, walkable dining, and easy beach access.
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Holiday travel
Fourth of July Stays in Holmes Beach (Anna Maria Island)
Celebrate the Fourth of July on Anna Maria Island with walk-to-beach access, a private heated pool, and a Holmes Beach home base.
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Long weekends
Fourth of July Week Stays in Holmes Beach (Anna Maria Island)
Book a full Fourth of July Week on Anna Maria Island with a private heated pool, beach access, and a relaxed Holmes Beach base.
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Family breaks
Fourth of July Weekend Stays in Holmes Beach (Anna Maria Island)
Spend Fourth of July Weekend in Holmes Beach with walk-to-beach access, a private heated pool, and easy island dining.
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Couples escapes
Labor Day Weekend Stays in Holmes Beach (Anna Maria Island)
Wrap up summer with Labor Day Weekend in Holmes Beach, featuring walk-to-beach access and a private heated pool.
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Holiday travel
Labor Day Week Stays in Holmes Beach (Anna Maria Island)
Book a Labor Day Week stay in Holmes Beach for late-summer beach time, a private heated pool, and easy island routines.
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Long weekends
Veterans Day Weekend Stays in Holmes Beach (Anna Maria Island)
Plan a Veterans Day Weekend trip to Holmes Beach with a private heated pool, beach access, and a calm fall rhythm.
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Family breaks
Indigenous Peoples Day Weekend Stays in Holmes Beach (Anna Maria Island)
Take an Indigenous Peoples Day Weekend escape to Holmes Beach with a private heated pool and walk-to-beach access.
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Couples escapes
Fall Break Stays in Holmes Beach (Anna Maria Island)
Plan a Fall Break stay in Holmes Beach with a private heated pool, walk-to-beach access, and an easy island pace.
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Holiday travel
Halloween Week Stays in Holmes Beach (Anna Maria Island)
Spend Halloween Week on Anna Maria Island with beach days, a private heated pool, and a relaxed Holmes Beach base.
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Long weekends
Halloween Weekend Stays in Holmes Beach (Anna Maria Island)
Book a Halloween Weekend stay in Holmes Beach with walk-to-beach access, a private heated pool, and an easy island vibe.
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Family breaks
Thanksgiving Stays in Holmes Beach (Anna Maria Island)
Plan a Thanksgiving stay on Anna Maria Island with a private heated pool, walk-to-beach access, and a calm Holmes Beach home base.
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Couples escapes
Thanksgiving Week Stays in Holmes Beach (Anna Maria Island)
Book a Thanksgiving Week in Holmes Beach with a private heated pool, beach access, and easy island routines.
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Holiday travel
Thanksgiving Weekend Stays in Holmes Beach (Anna Maria Island)
Take a Thanksgiving Weekend break in Holmes Beach with a private heated pool, walkable dining, and easy beach access.
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Long weekends
Christmas Stays in Holmes Beach (Anna Maria Island)
Spend Christmas on Anna Maria Island with a private heated pool, walk-to-beach access, and a calm Holmes Beach base.
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Family breaks
Christmas Week Stays in Holmes Beach (Anna Maria Island)
Book a Christmas Week stay in Holmes Beach with a private heated pool, beach access, and easy holiday routines.
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Couples escapes
Christmas Weekend Stays in Holmes Beach (Anna Maria Island)
Celebrate Christmas Weekend in Holmes Beach with a private heated pool, walk-to-beach access, and easy island dining.
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Holiday travel
Hanukkah Stays in Holmes Beach (Anna Maria Island)
Spend Hanukkah on Anna Maria Island with a private heated pool, beach access, and a relaxed Holmes Beach base.
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Long weekends
Winter Break Stays in Holmes Beach (Anna Maria Island)
Plan a Winter Break stay in Holmes Beach with a private heated pool, walk-to-beach access, and an easy island routine.
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Family breaks
Winter Holiday Week Stays in Holmes Beach (Anna Maria Island)
Book a Winter Holiday Week in Holmes Beach with a private heated pool, walkable dining, and easy beach access.
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Couples escapes
Midwinter Break Stays in Holmes Beach (Anna Maria Island)
Take a Midwinter Break in Holmes Beach with a private heated pool, walk-to-beach access, and a calm island vibe.
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Planning a holiday stay?
Choose a holiday guide, then match it to open dates for a low-stress beach trip. Private pool, walk-to-beach access, and a calm Holmes Beach base.