Seasonal travel on Anna Maria Island
Seasonal Trip Guides
Find the best time of year for your Holmes Beach getaway. These seasonal guides highlight the pace, weather feel, and open-date timing that make planning easier.
Seasonal travel
January Beach Weeks in Holmes Beach (Anna Maria Island)
Plan January beach weeks in Holmes Beach with a private heated pool, walk-to-beach access, and a relaxed island rhythm.
Read more->
Quiet weeks
February Beach Weeks in Holmes Beach (Anna Maria Island)
Plan February beach weeks on Anna Maria Island with a private heated pool, walkable dining, and easy beach access.
Read more->
Family timing
March Spring Weeks in Holmes Beach (Anna Maria Island)
Book March spring weeks in Holmes Beach with a private heated pool, walk-to-beach access, and a relaxed island pace.
Read more->
Couples time
April Spring Weeks in Holmes Beach (Anna Maria Island)
Plan April spring weeks on Anna Maria Island with a private heated pool, walkable dining, and a calm Holmes Beach base.
Read more->
Seasonal travel
May Pre-Summer Weeks in Holmes Beach (Anna Maria Island)
Plan May pre-summer weeks in Holmes Beach with a private heated pool, walk-to-beach access, and easy island routines.
Read more->
Quiet weeks
June Summer Weeks in Holmes Beach (Anna Maria Island)
Book June summer weeks in Holmes Beach with a private heated pool, walkable dining, and easy beach access.
Read more->
Family timing
July Summer Weeks in Holmes Beach (Anna Maria Island)
Plan July summer weeks on Anna Maria Island with a private heated pool, walk-to-beach access, and a relaxed Holmes Beach base.
Read more->
Couples time
August Late-Summer Weeks in Holmes Beach (Anna Maria Island)
Book August late-summer weeks in Holmes Beach with a private heated pool, walkable dining, and easy beach access.
Read more->
Seasonal travel
September Shoulder Season in Holmes Beach (Anna Maria Island)
Plan September shoulder-season stays in Holmes Beach with a private heated pool, walk-to-beach access, and a quieter island pace.
Read more->
Quiet weeks
October Fall Beach Weeks in Holmes Beach (Anna Maria Island)
Book October fall beach weeks in Holmes Beach with a private heated pool, walkable dining, and easy beach access.
Read more->
Family timing
November Fall Beach Weeks in Holmes Beach (Anna Maria Island)
Plan November fall beach weeks in Holmes Beach with a private heated pool, walk-to-beach access, and an easy island rhythm.
Read more->
Couples time
December Holiday Sun in Holmes Beach (Anna Maria Island)
Spend December in Holmes Beach with holiday sun, a private heated pool, and easy beach access.
Read more->
Seasonal travel
Winter Sun Escapes in Holmes Beach (Anna Maria Island)
Plan a winter sun escape to Holmes Beach with a private heated pool, walkable dining, and easy beach access.
Read more->
Quiet weeks
Snowbird Stays in Holmes Beach (Anna Maria Island)
Plan snowbird stays in Holmes Beach with a private heated pool, walk-to-beach access, and a relaxed island routine.
Read more->
Family timing
Extended Monthly Stays in Holmes Beach (Anna Maria Island)
Plan extended monthly stays in Holmes Beach with a private heated pool, walkable dining, and easy beach access.
Read more->
Couples time
Early Spring Resets in Holmes Beach (Anna Maria Island)
Plan early spring reset trips to Holmes Beach with a private heated pool, walk-to-beach access, and easy island routines.
Read more->
Seasonal travel
Late Spring Sun in Holmes Beach (Anna Maria Island)
Book late spring sun trips to Holmes Beach with a private heated pool, walkable dining, and easy beach access.
Read more->
Quiet weeks
Early Summer Kickoff in Holmes Beach (Anna Maria Island)
Kick off summer in Holmes Beach with a private heated pool, walk-to-beach access, and an easy island pace.
Read more->
Family timing
Midsummer Family Weeks in Holmes Beach (Anna Maria Island)
Plan midsummer family weeks in Holmes Beach with a private heated pool, walkable dining, and easy beach access.
Read more->
Couples time
Late Summer Deals in Holmes Beach (Anna Maria Island)
Find late summer deals in Holmes Beach with a private heated pool, walk-to-beach access, and a calm island rhythm.
Read more->
Seasonal travel
Early Fall Resets in Holmes Beach (Anna Maria Island)
Plan early fall reset trips to Holmes Beach with a private heated pool, walk-to-beach access, and easy island routines.
Read more->
Quiet weeks
Late Fall Warmth in Holmes Beach (Anna Maria Island)
Chase late fall warmth in Holmes Beach with a private heated pool, walkable dining, and easy beach access.
Read more->
Family timing
Shoulder Season Deals in Holmes Beach (Anna Maria Island)
Find shoulder season deals in Holmes Beach with a private heated pool, walk-to-beach access, and a calm island pace.
Read more->
Couples time
Quiet Season Stays in Holmes Beach (Anna Maria Island)
Plan quiet season stays in Holmes Beach with a private heated pool, walkable dining, and easy beach access.
Read more->
Seasonal travel
Pool Season in Holmes Beach (Anna Maria Island)
Plan pool season stays in Holmes Beach with a private heated pool, walk-to-beach access, and easy island routines.
Read more->
Quiet weeks
Beach Morning Season in Holmes Beach (Anna Maria Island)
Plan beach morning season stays in Holmes Beach with walk-to-beach access, a private heated pool, and easy island routines.
Read more->
Family timing
Sunset Season in Holmes Beach (Anna Maria Island)
Plan sunset season stays in Holmes Beach with walk-to-beach access, a private heated pool, and easy island routines.
Read more->
Couples time
Walkable Season in Holmes Beach (Anna Maria Island)
Plan walkable season stays in Holmes Beach with easy access to the beach, Pine Avenue, and Bridge Street.
Read more->
Seasonal travel
Pet-Friendly Season in Holmes Beach (Anna Maria Island)
Plan pet-friendly season stays in Holmes Beach with walk-to-beach access and a private heated pool. Small dogs 35 lbs or less welcome.
Read more->
Quiet weeks
Couples Season in Holmes Beach (Anna Maria Island)
Plan couples season stays in Holmes Beach with a private heated pool, walkable dining, and easy beach access.
Read more->
Family timing
Family Season in Holmes Beach (Anna Maria Island)
Plan family season stays in Holmes Beach with a private heated pool, walk-to-beach access, and easy island routines.
Read more->
Couples time
Wellness Season in Holmes Beach (Anna Maria Island)
Plan wellness season stays in Holmes Beach with a private heated pool, walkable beach access, and a calm island pace.
Read more->
Seasonal travel
Foodie Season in Holmes Beach (Anna Maria Island)
Plan foodie season stays in Holmes Beach with walkable dining, a private heated pool, and easy beach access.
Read more->
Quiet weeks
Fishing Season in Holmes Beach (Anna Maria Island)
Plan fishing season stays in Holmes Beach with a private heated pool, easy beach access, and a calm home base after time on the water.
Read more->
Family timing
Trolley Season in Holmes Beach (Anna Maria Island)
Plan trolley season stays in Holmes Beach with easy access to the free island trolley, walkable beaches, and a private heated pool.
Read more->
Couples time
Bay Sunrise Season in Holmes Beach (Anna Maria Island)
Plan bay sunrise season stays in Holmes Beach with calm mornings, walkable beach access, and a private heated pool.
Read more->
Seasonal travel
Island Hopping Season in Holmes Beach (Anna Maria Island)
Plan island hopping season stays in Holmes Beach with easy access to Anna Maria City, Bradenton Beach, and a private heated pool.
Read more->
Quiet weeks
Weekend Escape Season in Holmes Beach (Anna Maria Island)
Plan weekend escape season stays in Holmes Beach with walk-to-beach access, a private heated pool, and an easy island rhythm.
Read more->
Family timing
Midweek Escapes in Holmes Beach (Anna Maria Island)
Plan midweek escape stays in Holmes Beach with a private heated pool, walk-to-beach access, and a calm island pace.
Read more->
Couples time
Last-Minute Season in Holmes Beach (Anna Maria Island)
Find last-minute season stays in Holmes Beach with a private heated pool, walkable dining, and easy beach access.
Read more->
Choose your season
Pick the timing that fits your trip style, then match it to open dates for a low-stress beach escape in Holmes Beach.