Houses in Anna Maria Island, FL
Houses in Anna Maria Island, FL, from $93 a night. Book direct on each manager's site, no OTA fee.
Find stays in Anna Maria Island, FL
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Stays, best documented first
Bayou Vista Retreat
House · 3 bed · 2 bath · sleeps 6
Bradenton, FL
From $100 a night
- kitchen
- wifi
- free parking on premises
- tv
Exact location
Book direct on Anna Maria Island Vacation Homes
Dans Florida Condos Island Charm at Runaway Bay
House · 2 bed · 2 bath · sleeps 6
Bradenton Beach, FL
From $133 a night
- beach access
- kitchen
- fast wifi – 368 mbps
- dedicated workspace
Exact location
Book direct on Dan's Florida Condos
Dans Florida Condos Sea Pelican At Runaway Bay
House · 1 bed · 1 bath · sleeps 4
Bradenton Beach, FL
From $135 a night
- beach access
- kitchen
- fast wifi – 644 mbps
- dedicated workspace
Exact location
Book direct on Dan's Florida Condos
Happy Island Cottage
House · 3 bed · 2.5 bath · sleeps 6
Holmes Beach, FL
From $265 a night
- pet friendly
- new fancy ocean wave looking metal roof
- central air
- fast wi-fi
Exact location
Book direct on Happy Island Cottage: Anna Maria Island rentals, book direct
Island Break
House · 2 bed · 2 bath · sleeps 6
Holmes Beach, FL
From $273 a night
- beach access
- kitchen
- wifi
- free parking on premises
Exact location
Book direct on Anna Maria Island Vacation Homes
Island Interlude
House · 2 bed · 2 bath · sleeps 6
Holmes Beach, FL
From $273 a night
- kitchen
- wifi
- free parking on premises
- shared outdoor pool - available all year
Exact location
Book direct on Anna Maria Island Vacation Homes
Beach House Resort #8
House · 1 bed · 1 bath · sleeps 2
Bradenton Beach, FL
From $275 a night
- ocean view
- shared beach access – beachfront
- kitchen
- wifi
Exact location
Book direct on Anna Maria Island Vacation Homes
Seas The Day
House · 2 bed · 2 bath · sleeps 5
Bradenton, FL
From $315 a night
- kitchen
- wifi
- free parking on premises
- shared pool - heated
Exact location
Book direct on Anna Maria Island Vacation Homes
Sunrise On The Bay
House · 2 bed · 2 bath · sleeps 6
Bradenton Beach, FL
From $335 a night
- beach access
- kitchen
- wifi
- free parking on premises
Exact location
Book direct on Anna Maria Island Vacation Homes
Poolside Paradise
House · 3 bed · 2 bath · sleeps 10
Bradenton, FL
From $473 a night
- internet / wifi
- air conditioning
- central heating
- linens provided
Exact location
Book direct on Anna Maria Island Vacation Homes
Shore To Please
House · 4 bed · 4 bath · sleeps 8
Holmes Beach, FL
From $550 a night
- kitchen
- wifi
- free parking on premises – 4 spaces
- exterior security cameras on property
Exact location
Book direct on Anna Maria Island Vacation Homes
Sail Away
House · 4 bed · 4 bath · sleeps 8
Holmes Beach, FL
From $588 a night
- beach access
- kitchen
- wifi
- free residential garage on premises – 4
Exact location
Book direct on Anna Maria Island Vacation Homes
Tiny Carriage House Riverwalk, Downtown
House · 1 bed · 1.5 bath · sleeps 3
Bradenton, FL
From $110 a night
- air conditioning
- central heating
- linens provided
- towels provided
Exact location
Book direct on The Amazing Co-Host, Short Term Rentals
Sun and Sand Getaway
House · 3 bed · 3 bath · sleeps 6
Bradenton, FL
From $131 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on .
915 Palma Rosa
House · 2 bed · 2 bath
Bradenton, FL
From $160 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on Wisconsin & Bradenton Vacation Rentals
919 Palma Janoli
House · 3 bed · 2 bath
Bradenton, FL
From $160 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on Wisconsin & Bradenton Vacation Rentals
Island Girl East
House · 2 bed · 2 bath · sleeps 5
Anna Maria, FL
From $162 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Island Girl West
House · 2 bed · 2 bath · sleeps 5
Anna Maria, FL
From $162 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
L'Oasis East
House · 2 bed · 2 bath · sleeps 4
Anna Maria, FL
From $178 a night
- dryer
- hair dryer
- hangers
- heating
City-level location
Book direct on Anna Maria Island Beach Rentals
L'Oasis West
House · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $178 a night
- dryer
- hair dryer
- hangers
- heating
City-level location
Book direct on Anna Maria Island Beach Rentals
The Bahamas
House · 4 bed · 2 bath · sleeps 8
Bradenton, FL
From $182 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Driftwood Cottage
House · 4 bed · 2 bath · sleeps 6
Bradenton, FL
From $184 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Catching Waves
House · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $185 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Once Upon a Pond
House · 4 bed · 3 bath · sleeps 9
Bradenton, FL
From $192 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Palm Haven
House · 4 bed · 2 bath · sleeps 6
Bradenton, FL
From $194 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Cozy Cabana East
House · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $196 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Lucky Charm
House · 4 bed · 3 bath · sleeps 7
Bradenton, FL
From $201 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Aqua Palm
House · 4 bed · 3 bath · sleeps 11
Bradenton, FL
From $206 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Casa Del Mar
House · 5 bed · 3 bath · sleeps 10
Bradenton, FL
From $206 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Coco Vista
House · 4 bed · 3 bath · sleeps 7
Bradenton, FL
From $206 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Florisun
House · 4 bed · 2 bath · sleeps 7
Sarasota, FL
From $206 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Royal Eden
House · 4 bed · 3 bath · sleeps 6
Bradenton, FL
From $206 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Fins Up
House · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $207 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
AMI Beach Home 2 BR, 201 69th St., Holmes Beach, Florida
House · 2 bed · 3 bath · sleeps 4
Holmes Beach, FL
From $209 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on Anna Maria Island!
Hidden Palms
House · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $211 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
AMI Beach Home 3 BR, 201 69th St., Holmes Beach, Florida
House · 3 bed · 3 bath · sleeps 5
Holmes Beach, FL
From $223 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on Anna Maria Island!
Riverside Château
House · 4 bed · 3 bath · sleeps 6
Bradenton, FL
From $225 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Lakeshore
House · 5 bed · 2 bath · sleeps 8
Bradenton, FL
From $227 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Maison de la Mer
House · 4 bed · 3 bath · sleeps 7
Bradenton, FL
From $227 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Robinson Recluse
House · 4 bed · 4 bath · sleeps 9
Bradenton, FL
From $227 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Camingo
House · 4 bed · 3 bath · sleeps 8
Bradenton, FL
From $236 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
SPECIALS FOR COUPLES ! BIG SUNNY QUITE POOL ! Beach, restaurants, shopping
House · 3 bed · 2 bath · sleeps 3
Bradenton, FL
From $239 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on Sunnyside NW
Sandy Pants
House · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $242 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Mahalo
House · 5 bed · 3 bath · sleeps 8
Bradenton, FL
From $244 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Your home away from home
House · 3 bed · 2 bath · sleeps 6
Sarasota, FL
From $250 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair accessible
Exact location
Book direct on The Sea is Calling 2.0
Mango Bay
House · 2 bed · 3 bath · sleeps 8
Anna Maria, FL
From $252 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Paradise Awaits
House · 5 bed · 4 bath · sleeps 9
Bradenton, FL
From $256 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Moroccan Moon
House · 5 bed · 4 bath · sleeps 8
Bradenton, FL
From $260 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Vela Mar
House · 2 bed · 4 bath · sleeps 8
Anna Maria, FL
From $261 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Champion Retreat
House · 5 bed · 5 bath · sleeps 9
Bradenton, FL
From $268 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Moonlit Cove
House · 5 bed · 3 bath · sleeps 8
Bradenton, FL
From $268 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
AMI Beach Home 4 BR, 201 69th St., Holmes Beach, Florida
House · 4 bed · 4 bath · sleeps 6
Holmes Beach, FL
From $273 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on Anna Maria Island!
Bonjour AMI
House · 5 bed · 5 bath · sleeps 8
Bradenton, FL
From $288 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
Point's Hideaway
House · 2 bed · 3 bath · sleeps 8
Anna Maria, FL
From $296 a night
- bed linens
- cable/satellite tv
- clothing storage
- dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
AMI Peppertree Paradise
House · 2 bed · 2 bath · sleeps 8
Anna Maria, FL
From $304 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
Royal Palms
House · 5 bed · 4 bath · sleeps 11
Bradenton, FL
From $304 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on STAYAWHILEWITHUS
She's Always Right
House · 2 bed · 4 bath · sleeps 8
Anna Maria, FL
From $304 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
7mi to AMI w/ Pickleball+Golf | Htd Pool+Tiki Hut
House · 5 bed · 3 bath · sleeps 16
Bradenton, FL
From $315 a night
- internet
- wireless
- air conditioning
- swimming pool
Exact location
Book direct on Poconos Vacation Rentals
Sol Mate
House · 2 bed · 2 bath · sleeps 8
Anna Maria, FL
From $315 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
The Palm at Bean Point
House · 2 bed · 2 bath · sleeps 6
Anna Maria, FL
From $324 a night
- bed linens
- clothing storage
- dryer
- hair dryer
City-level location
Book direct on Anna Maria Island Beach Rentals
These are the cheapest; there are more. Narrow by facet above, or ask an agent through https://otaless.com/mcp.
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Managers here
How prices are computed
Lowest rate the manager has published. Your dates may cost more; the real price is on their site. The "from" figure is the lowest nightly rate the manager published on that listing page when we last fetched it. It excludes taxes, cleaning and other fees, it is not a quote, and it is not live availability.
Updated 2026-10-31 08:46 UTC. Prices and facts are whatever the manager published on their own site.