Holiday travel on Anna Maria Island
Holiday Weeks in Holmes Beach
Every stay at The Sandbox is at least 7 nights, so each guide builds a full week around the holiday, soonest first. Each one checks the live calendar for that week, so you can see at a glance whether it is still open.
Holiday travel
Halloween Week Stays in Holmes Beach (Anna Maria Island)
Halloween Week: Sat, Oct 31, 2026
Spend Halloween Week on Anna Maria Island with beach days, a private saltwater pool, and a relaxed Holmes Beach base.
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Holiday weeks
A Week Around Halloween Weekend on Anna Maria Island (Holmes Beach)
Halloween Weekend: Sat, Oct 31, 2026
Book a week around Halloween in Holmes Beach with direct beach access, a private saltwater pool, and an easy island vibe.
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Family breaks
A Week Around Veterans Day Weekend on Anna Maria Island (Holmes Beach)
Veterans Day Weekend: Wed, Nov 11, 2026
Plan a week around Veterans Day in Holmes Beach with a private saltwater pool, beach access, and a calm fall rhythm.
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Couples escapes
Thanksgiving Stays in Holmes Beach (Anna Maria Island)
Thanksgiving: Thu, Nov 26, 2026
Plan a Thanksgiving week on Anna Maria Island with a private saltwater pool, direct beach access, and a calm Holmes Beach home base.
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Holiday travel
Thanksgiving Week Stays in Holmes Beach (Anna Maria Island)
Thanksgiving Week: Thu, Nov 26, 2026
Book a Thanksgiving Week in Holmes Beach with a private saltwater pool, beach access, and easy island routines.
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Holiday weeks
A Week Around Thanksgiving Weekend on Anna Maria Island (Holmes Beach)
Thanksgiving Weekend: Thu, Nov 26, 2026
Plan a week in Holmes Beach around Thanksgiving weekend, with a private saltwater pool, dinners out, and direct beach access.
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Family breaks
Hanukkah Stays in Holmes Beach (Anna Maria Island)
Hanukkah: Fri, Dec 4, 2026
Spend Hanukkah on Anna Maria Island with a private saltwater pool, beach access, and a relaxed Holmes Beach base.
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Couples escapes
Christmas Stays in Holmes Beach (Anna Maria Island)
Christmas: Fri, Dec 25, 2026
Spend Christmas on Anna Maria Island with a private saltwater pool, direct beach access, and a calm Holmes Beach base.
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Holiday travel
Christmas Week Stays in Holmes Beach (Anna Maria Island)
Christmas Week: Fri, Dec 25, 2026
Book a Christmas Week stay in Holmes Beach with a private saltwater pool, beach access, and easy holiday routines.
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Holiday weeks
A Week Around Christmas Weekend on Anna Maria Island (Holmes Beach)
Christmas Weekend: Fri, Dec 25, 2026
Make Christmas weekend part of a full week in Holmes Beach, with a private saltwater pool, direct beach access, and easy island dining.
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Family breaks
New Year's Week in Holmes Beach: A 7-Night Stay Over the Holidays
New Year's Week: Thu, Dec 31, 2026
Spend New Year's Eve and New Year's Day in a Holmes Beach cottage one house off the beach: a 7-night stay with a private saltwater pool, and the live calendar for the week.
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Couples escapes
A Week Around MLK Weekend on Anna Maria Island (Holmes Beach)
MLK Weekend: Mon, Jan 18, 2027
Plan a week in Holmes Beach around MLK weekend, with direct beach access, a private saltwater pool, and easy island dining.
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Holiday travel
A Week Around Valentine's Weekend on Anna Maria Island (Holmes Beach)
Valentine's Weekend: Sun, Feb 14, 2027
Plan a week around Valentine's Day in Holmes Beach with a private saltwater pool, dinners out, and quiet beach sunsets.
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Holiday weeks
A Week Around Presidents' Day Weekend on Anna Maria Island (Holmes Beach)
Presidents' Day Weekend: Mon, Feb 15, 2027
Spend a week in Holmes Beach around Presidents' Day weekend, with a private pool, direct beach access, and a calm island pace.
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Family breaks
Presidents' Week Stays in Holmes Beach (Anna Maria Island)
Presidents' Week: Mon, Feb 15, 2027
Plan a Presidents' Week stay on Anna Maria Island for beach time, a private saltwater pool, and easy family routines.
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Couples escapes
A Week Around Easter Weekend on Anna Maria Island (Holmes Beach)
Easter Weekend: Sun, Mar 28, 2027
Build a week around Easter weekend on Anna Maria Island, with beach walks, a private saltwater pool, and a peaceful Holmes Beach base.
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Holiday travel
Easter Week Stays in Holmes Beach (Anna Maria Island)
Easter Week: Sun, Mar 28, 2027
Plan an Easter Week stay in Holmes Beach with a private saltwater pool, direct beach access, and an easy island rhythm.
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Holiday weeks
A Week Around Mother's Day Weekend on Anna Maria Island (Holmes Beach)
Mother's Day Weekend: Sun, May 9, 2027
Treat mom to a week in Holmes Beach around Mother's Day, with a private saltwater pool, beach walks, and easy dining nearby.
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Family breaks
A Week Around Memorial Day Weekend on Anna Maria Island (Holmes Beach)
Memorial Day Weekend: Mon, May 31, 2027
Kick off summer with a week in Holmes Beach around Memorial Day weekend: direct beach access, a private pool, and a relaxed island vibe.
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Couples escapes
Memorial Day Week Stays in Holmes Beach (Anna Maria Island)
Memorial Day Week: Mon, May 31, 2027
Plan a Memorial Day Week stay in Holmes Beach with a private saltwater pool, direct beach access, and a calm island routine.
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Holiday travel
A Week Around Father's Day Weekend on Anna Maria Island (Holmes Beach)
Father's Day Weekend: Sun, Jun 20, 2027
Plan a week around Father's Day in Holmes Beach with a private saltwater pool, a gas grill, and direct beach access.
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Holiday weeks
Fourth of July Week 2027 in Holmes Beach, Anna Maria Island
Fourth of July: Sun, Jul 4, 2027
Plan the Fourth of July 2027 on Anna Maria Island: a 7-night stay in a Holmes Beach cottage one house off the beach, with a private saltwater pool, the live calendar for July 4th week, and where the parade runs.
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Family breaks
A Week Around Labor Day Weekend on Anna Maria Island (Holmes Beach)
Labor Day Weekend: Mon, Sep 6, 2027
Wrap up summer with a week in Holmes Beach around Labor Day weekend, with direct beach access and a private saltwater pool.
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Couples escapes
Labor Day Week Stays in Holmes Beach (Anna Maria Island)
Labor Day Week: Mon, Sep 6, 2027
Book a Labor Day Week stay in Holmes Beach for late-summer beach time, a private saltwater pool, and easy island routines.
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Holiday travel
A Week Around Indigenous Peoples Day Weekend on Anna Maria Island (Holmes Beach)
Indigenous Peoples Day Weekend: Mon, Oct 11, 2027
Take a week around Indigenous Peoples Day in Holmes Beach with a private saltwater pool and direct beach access.
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Holiday weeks
Spring Break Stays in Holmes Beach (Anna Maria Island)
Book a Spring Break week on Anna Maria Island with direct beach access, a private saltwater pool, and a relaxed Holmes Beach base.
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Family breaks
Spring Break Week Stays in Holmes Beach (Anna Maria Island)
Plan a full Spring Break week in Holmes Beach with a private pool, casual spots within walking distance, and direct 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 saltwater pool, direct beach access, and an easy island pace.
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Holiday travel
Winter Break Stays in Holmes Beach (Anna Maria Island)
Plan a Winter Break stay in Holmes Beach with a private saltwater pool, direct beach access, and an easy island routine.
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Holiday weeks
Winter Holiday Week Stays in Holmes Beach (Anna Maria Island)
Book a Winter Holiday Week in Holmes Beach with a private saltwater pool, casual spots within walking distance, and direct beach access.
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Family breaks
Midwinter Break Stays in Holmes Beach (Anna Maria Island)
Take a Midwinter Break week in Holmes Beach with a private saltwater pool, direct 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 week. Private saltwater pool, direct beach access one house off the beach, and a calm Holmes Beach base for up to 6 guests.